(-)-Benzyl 2,3-dide-oxy-β-d-erythro-hex-2-eno-pyran-oside.

In the title compound, C13H16O4, the six-membered ring of the sugar moiety shows a half-chair conformation. In the crystal, mol-ecules are connected via O-H⋯O hydrogen bonds, forming columns around twofold screw axes along the b-axis direction. There is a disorder of the benz-yloxy group, which has two possible orientations with the phenyl group lying on a common plane [site-occupancy factors = 0.589 (9) and 0.411 (9)].

Related literature

For the phenolic Ferrier reaction, see: Ferrier & Prasad (1969 ▶); Noshita et al. (1995 ▶). For the structure of the related compound α-glycoside, see: Wingert et al. (1984 ▶). For the synthesis of β-glycoside, see: Di Bussolo et al. (2002 ▶, 2004 ▶). For the enzymatic regioselective acyl­ation of d-glucal, see: Calveras et al. (2010 ▶).

Experimental

Crystal data

C13H16O4

M = 236.26

Monoclinic,

a = 19.500 (9) Å

b = 5.291 (2) Å

c = 6.0809 (15) Å

β = 94.27 (3)°

V = 625.7 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 292 K

0.60 × 0.40 × 0.20 mm

Data collection

Rigaku AFC-7R diffractometer

1713 measured reflections

1585 independent reflections

786 reflections with F 2 > 2σ(F 2)

R int = 0.034

3 standard reflections every 150 reflections intensity decay: 0.8%

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.255

S = 1.04

1579 reflections

193 parameters

33 restraints

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.17 e Å−3

Data collection: WinAFC Diffractometer Control Software (Rigaku, 1999 ▶); cell refinement: WinAFC Diffractometer Control Software (Rigaku, 1999 ▶); data reduction: CrystalStructure (Rigaku, 2010 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: CrystalStructure (Rigaku, 2010 ▶).

Crystal structure: contains datablock(s) General, I. DOI: 10.1107/S1600536813031140/is5321sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813031140/is5321Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813031140/is5321Isup3.cdx

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C13H16O4	F(000) = 252.00
Mr = 236.26	Dx = 1.254 Mg m−3
Monoclinic, P21	Melting point = 353–354 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71069 Å
a = 19.500 (9) Å	Cell parameters from 25 reflections
b = 5.291 (2) Å	θ = 10.1–12.5°
c = 6.0809 (15) Å	µ = 0.09 mm−1
β = 94.27 (3)°	T = 292 K
V = 625.7 (4) Å3	Plate, colorless
Z = 2	0.60 × 0.40 × 0.20 mm

Rigaku AFC-7R diffractometer	Rint = 0.034
Radiation source: Rigaku rotating Mo anode	θmax = 27.5°
Graphite plate monochromator	h = −9→25
ω–2θ scans	k = 0→6
1713 measured reflections	l = −7→7
1585 independent reflections	3 standard reflections every 150 reflections
786 reflections with F2 > 2σ(F2)	intensity decay: 0.8%

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056	H-atom parameters constrained
wR(F2) = 0.255	w = 1/[σ2(Fo2) + (0.1473P)2 + 0.0601P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
1579 reflections	Δρmax = 0.16 e Å−3
193 parameters	Δρmin = −0.17 e Å−3
33 restraints	Absolute structure: see text
Primary atom site location: structure-invariant direct methods

Experimental. Spectroscopic data: IR ν max: 3292, 2937, 2872, 1377, 1325, 1176, 1144, 1122, 1051, 970, 951, 876, 787, 744, 696 cm-1; 1H NMR (CDCl3): δ = 7.26–7.40 (m, 5H), 6.14 (ddd, J = 1.3, 4.6, 10.0 Hz, 1H), 5.89 (ddd, J = 1.0, 1.1, 10.0 Hz, 1H), 5.18 (ddd, J = 1.1, 1.3, 1.5 Hz, 1H), 4.92 (d, J = 11.8 Hz, 1H), 4.70 (d, J = 11.8 Hz, 1H), 4.02–4.09 (m, 1H), 3.97 (ddd, J = 5.9, 6.7, 12.0 Hz, 1H), 3.88 (ddd, J = 4.3, 7.3, 12.0 Hz, 1H), 3.79 (ddd, J = 3.1, 4.3, 6.7 Hz, 1H), 2.21 (dd, J = 5.9, 7.3 Hz, 1H), 1.97 (d, J = 10.6 Hz, 1H); 13C NMR (CDCl3): δ = 137.2, 130.9, 130.2, 128.4, 128.0, 127.9, 96.5, 75.1, 70.3, 62.9, 62.5.

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factor (gt).

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.3098 (2)	0.1914 (7)	0.7411 (7)	0.0920 (13)
O2	0.4326 (4)	−0.2905 (9)	0.9178 (11)	0.152 (3)
O3	0.4652 (2)	0.2679 (10)	0.7637 (8)	0.0988 (14)
O4A	0.2323 (7)	0.485 (3)	0.5340 (18)	0.090 (4)	0.589 (9)
O4B	0.2402 (8)	0.476 (4)	0.638 (2)	0.068 (4)	0.411 (9)
C5	0.3777 (5)	−0.1093 (15)	0.9332 (13)	0.116 (3)
C6	0.3606 (3)	0.0062 (11)	0.7108 (10)	0.0822 (15)
C7	0.4216 (3)	0.1300 (14)	0.6082 (9)	0.0837 (16)
C8	0.3960 (3)	0.2985 (17)	0.4253 (8)	0.0933 (19)
C9	0.3317 (3)	0.3656 (15)	0.3939 (10)	0.096 (2)
C10	0.2796 (3)	0.2768 (14)	0.5335 (12)	0.0946 (17)
C11A	0.1683 (5)	0.409 (3)	0.605 (3)	0.097 (4)	0.589 (9)
C11B	0.1941 (7)	0.406 (4)	0.797 (4)	0.107 (6)	0.411 (9)
C12A	0.1400 (7)	0.603 (3)	0.754 (2)	0.078 (4)	0.589 (9)
C12B	0.1432 (11)	0.611 (4)	0.826 (4)	0.078 (4)	0.411 (9)
C13A	0.1743 (7)	0.635 (3)	0.960 (2)	0.108 (4)	0.589 (9)
C13B	0.1432 (12)	0.747 (5)	1.019 (4)	0.108 (4)	0.411 (9)
C14A	0.1520 (9)	0.811 (4)	1.107 (3)	0.153 (8)	0.589 (9)
C14B	0.0960 (16)	0.938 (7)	1.038 (5)	0.153 (8)	0.411 (9)
C15A	0.0936 (10)	0.947 (4)	1.041 (3)	0.143 (8)	0.589 (9)
C15B	0.0485 (15)	0.990 (5)	0.867 (4)	0.143 (8)	0.411 (9)
C16A	0.0592 (8)	0.927 (3)	0.837 (3)	0.109 (4)	0.589 (9)
C16B	0.0481 (10)	0.852 (4)	0.674 (3)	0.109 (4)	0.411 (9)
C17A	0.0842 (9)	0.750 (3)	0.696 (3)	0.095 (4)	0.589 (9)
C17B	0.0940 (15)	0.661 (5)	0.659 (5)	0.095 (4)	0.411 (9)
H2	0.4679	−0.2355	0.9822	0.1820*
H3	0.4543	0.4176	0.7592	0.1185*
H51	0.3919	0.0215	1.0387	0.1391*
H52	0.3374	−0.1926	0.9836	0.1391*
H6	0.3411	−0.1243	0.6103	0.0986*
H7	0.4491	−0.0040	0.5463	0.1005*
H8	0.4271	0.3589	0.3291	0.1120*
H9	0.3188	0.4743	0.2779	0.1150*
H10A	0.2558	0.1336	0.4596	0.1135*	0.589 (9)
H10B	0.2496	0.1490	0.4601	0.1135*	0.411 (9)
H11A	0.1737	0.2499	0.6832	0.1165*	0.589 (9)
H11B	0.1361	0.3836	0.4779	0.1165*	0.589 (9)
H11C	0.2197	0.3725	0.9365	0.1280*	0.411 (9)
H11D	0.1701	0.2528	0.7494	0.1280*	0.411 (9)
H13A	0.2127	0.5360	1.0006	0.1298*	0.589 (9)
H13B	0.1750	0.7105	1.1365	0.1298*	0.411 (9)
H14A	0.1753	0.8367	1.2442	0.1836*	0.589 (9)
H14B	0.0965	1.0323	1.1672	0.1836*	0.411 (9)
H15A	0.0767	1.0598	1.1409	0.1720*	0.589 (9)
H15B	0.0164	1.1182	0.8812	0.1720*	0.411 (9)
H16A	0.0211	1.0264	0.7962	0.1307*	0.589 (9)
H16B	0.0168	0.8893	0.5555	0.1307*	0.411 (9)
H17A	0.0621	0.7311	0.5564	0.1141*	0.589 (9)
H17B	0.0920	0.5625	0.5324	0.1141*	0.411 (9)

	U11	U22	U33	U12	U13	U23
O1	0.089 (3)	0.071 (3)	0.121 (3)	0.007 (2)	0.040 (3)	−0.013 (3)
O2	0.198 (6)	0.072 (3)	0.169 (5)	0.023 (4)	−0.094 (5)	−0.033 (3)
O3	0.083 (3)	0.091 (3)	0.117 (3)	0.003 (3)	−0.029 (2)	−0.023 (3)
O4A	0.079 (6)	0.079 (5)	0.111 (8)	0.007 (5)	0.009 (7)	0.007 (8)
O4B	0.051 (6)	0.067 (6)	0.087 (9)	0.012 (5)	0.010 (7)	0.010 (9)
C5	0.132 (6)	0.088 (5)	0.128 (5)	0.001 (5)	0.010 (5)	0.019 (5)
C6	0.089 (4)	0.060 (3)	0.097 (4)	0.007 (3)	0.003 (3)	−0.022 (3)
C7	0.076 (3)	0.093 (4)	0.082 (3)	0.020 (3)	−0.000 (3)	−0.032 (3)
C8	0.080 (4)	0.128 (6)	0.073 (3)	0.004 (4)	0.012 (3)	−0.012 (4)
C9	0.086 (4)	0.118 (6)	0.083 (3)	0.005 (4)	−0.001 (3)	−0.008 (4)
C10	0.067 (3)	0.075 (4)	0.141 (5)	0.010 (4)	0.005 (4)	−0.015 (4)
C11A	0.057 (5)	0.094 (8)	0.141 (9)	−0.013 (6)	0.016 (6)	−0.026 (8)
C11B	0.060 (8)	0.116 (13)	0.146 (15)	0.024 (9)	0.023 (9)	0.042 (13)
C12A	0.062 (4)	0.084 (4)	0.088 (10)	0.003 (4)	0.002 (6)	0.018 (6)
C12B	0.062 (4)	0.084 (4)	0.088 (10)	0.003 (4)	0.002 (6)	0.018 (6)
C13A	0.107 (9)	0.109 (10)	0.106 (8)	0.002 (7)	−0.009 (7)	−0.000 (8)
C13B	0.107 (9)	0.109 (10)	0.106 (8)	0.002 (7)	−0.009 (7)	−0.000 (8)
C14A	0.159 (14)	0.19 (2)	0.107 (10)	−0.077 (16)	0.007 (9)	−0.040 (11)
C14B	0.159 (14)	0.19 (2)	0.107 (10)	−0.077 (16)	0.007 (9)	−0.040 (11)
C15A	0.169 (16)	0.104 (10)	0.171 (17)	0.018 (11)	0.109 (13)	0.011 (11)
C15B	0.169 (16)	0.104 (10)	0.171 (17)	0.018 (11)	0.109 (13)	0.011 (11)
C16A	0.096 (7)	0.100 (9)	0.134 (11)	0.022 (7)	0.031 (8)	−0.012 (7)
C16B	0.096 (7)	0.100 (9)	0.134 (11)	0.022 (7)	0.031 (8)	−0.012 (7)
C17A	0.076 (7)	0.087 (13)	0.121 (7)	0.032 (8)	0.004 (6)	0.004 (8)
C17B	0.076 (7)	0.087 (13)	0.121 (7)	0.032 (8)	0.004 (6)	0.004 (8)

O1—C6	1.416 (8)	C16B—C17B	1.36 (4)
O1—C10	1.426 (8)	O2—H2	0.820
O2—C5	1.445 (11)	O3—H3	0.820
O3—C7	1.424 (8)	C5—H51	0.970
O4A—C10	1.438 (17)	C5—H52	0.970
O4A—C11A	1.409 (18)	C6—H6	0.980
O4B—C10	1.477 (19)	C7—H7	0.980
O4B—C11B	1.42 (3)	C8—H8	0.930
C5—C6	1.499 (10)	C9—H9	0.930
C6—C7	1.531 (9)	C10—H10A	0.980
C7—C8	1.483 (9)	C10—H10B	0.980
C8—C9	1.304 (9)	C11A—H11A	0.970
C9—C10	1.449 (9)	C11A—H11B	0.970
C11A—C12A	1.499 (19)	C11B—H11C	0.970
C11B—C12B	1.49 (3)	C11B—H11D	0.970
C12A—C13A	1.388 (18)	C13A—H13A	0.930
C12A—C17A	1.36 (3)	C13B—H13B	0.930
C12B—C13B	1.38 (3)	C14A—H14A	0.930
C12B—C17B	1.37 (4)	C14B—H14B	0.930
C13A—C14A	1.38 (3)	C15A—H15A	0.930
C13B—C14B	1.38 (4)	C15B—H15B	0.930
C14A—C15A	1.38 (3)	C16A—H16A	0.930
C14B—C15B	1.37 (4)	C16B—H16B	0.930
C15A—C16A	1.37 (3)	C17A—H17A	0.930
C15B—C16B	1.39 (3)	C17B—H17B	0.930
C16A—C17A	1.38 (3)
C6—O1—C10	110.5 (5)	C7—C6—H6	108.989
C10—O4A—C11A	111.4 (12)	O3—C7—H7	108.061
C10—O4B—C11B	118.8 (16)	C6—C7—H7	108.071
O2—C5—C6	109.1 (7)	C8—C7—H7	108.069
O1—C6—C5	106.0 (6)	C7—C8—H8	118.624
O1—C6—C7	109.3 (5)	C9—C8—H8	118.631
C5—C6—C7	114.5 (6)	C8—C9—H9	118.863
O3—C7—C6	113.1 (5)	C10—C9—H9	118.877
O3—C7—C8	109.9 (6)	O1—C10—H10A	108.127
C6—C7—C8	109.5 (5)	O1—C10—H10B	112.184
C7—C8—C9	122.7 (6)	O4A—C10—H10A	108.127
C8—C9—C10	122.3 (6)	O4B—C10—H10B	112.183
O1—C10—O4A	117.6 (7)	C9—C10—H10A	108.128
O1—C10—O4B	92.3 (7)	C9—C10—H10B	112.184
O1—C10—C9	111.1 (5)	O4A—C11A—H11A	109.342
O4A—C10—C9	103.3 (8)	O4A—C11A—H11B	109.349
O4B—C10—C9	115.4 (9)	C12A—C11A—H11A	109.342
O4A—C11A—C12A	111.4 (11)	C12A—C11A—H11B	109.335
O4B—C11B—C12B	110.7 (18)	H11A—C11A—H11B	107.980
C11A—C12A—C13A	117.0 (12)	O4B—C11B—H11C	109.503
C11A—C12A—C17A	123.9 (12)	O4B—C11B—H11D	109.498
C13A—C12A—C17A	119.1 (14)	C12B—C11B—H11C	109.496
C11B—C12B—C13B	121.7 (19)	C12B—C11B—H11D	109.495
C11B—C12B—C17B	119 (2)	H11C—C11B—H11D	108.069
C13B—C12B—C17B	119 (2)	C12A—C13A—H13A	119.650
C12A—C13A—C14A	120.7 (13)	C14A—C13A—H13A	119.655
C12B—C13B—C14B	120 (2)	C12B—C13B—H13B	120.088
C13A—C14A—C15A	117.1 (15)	C14B—C13B—H13B	120.082
C13B—C14B—C15B	120 (3)	C13A—C14A—H14A	121.432
C14A—C15A—C16A	124.1 (18)	C15A—C14A—H14A	121.427
C14B—C15B—C16B	120 (3)	C13B—C14B—H14B	119.853
C15A—C16A—C17A	116.3 (15)	C15B—C14B—H14B	119.850
C15B—C16B—C17B	119 (2)	C14A—C15A—H15A	117.945
C12A—C17A—C16A	122.6 (15)	C16A—C15A—H15A	117.953
C12B—C17B—C16B	122 (3)	C14B—C15B—H15B	120.031
C5—O2—H2	109.474	C16B—C15B—H15B	120.027
C7—O3—H3	109.475	C15A—C16A—H16A	121.839
O2—C5—H51	109.847	C17A—C16A—H16A	121.842
O2—C5—H52	109.853	C15B—C16B—H16B	120.433
C6—C5—H51	109.854	C17B—C16B—H16B	120.424
C6—C5—H52	109.864	C12A—C17A—H17A	118.712
H51—C5—H52	108.286	C16A—C17A—H17A	118.718
O1—C6—H6	108.978	C12B—C17B—H17B	119.115
C5—C6—H6	108.981	C16B—C17B—H17B	119.099
C6—O1—C10—O4A	−173.3 (5)	C8—C9—C10—O4A	147.8 (7)
C6—O1—C10—O4B	−173.0 (4)	C8—C9—C10—O4B	124.1 (7)
C6—O1—C10—C9	−54.6 (6)	O4A—C11A—C12A—C13A	−68.8 (15)
C10—O1—C6—C5	−168.0 (4)	O4A—C11A—C12A—C17A	109.9 (13)
C10—O1—C6—C7	68.1 (5)	O4B—C11B—C12B—C13B	−111.9 (19)
C10—O4A—C11A—C12A	139.3 (9)	O4B—C11B—C12B—C17B	70 (2)
C11A—O4A—C10—O1	−74.9 (11)	C11A—C12A—C13A—C14A	179.4 (11)
C11A—O4A—C10—O4B	−75.6 (14)	C11A—C12A—C17A—C16A	179.8 (12)
C11A—O4A—C10—C9	162.3 (9)	C13A—C12A—C17A—C16A	−2 (3)
C10—O4B—C11B—C12B	−160.8 (10)	C17A—C12A—C13A—C14A	1 (2)
C11B—O4B—C10—O1	−58.0 (13)	C11B—C12B—C13B—C14B	178.8 (17)
C11B—O4B—C10—O4A	121 (3)	C11B—C12B—C17B—C16B	−177.4 (19)
C11B—O4B—C10—C9	−172.7 (11)	C13B—C12B—C17B—C16B	4 (4)
O2—C5—C6—O1	−176.5 (5)	C17B—C12B—C13B—C14B	−3 (4)
O2—C5—C6—C7	−56.0 (7)	C12A—C13A—C14A—C15A	2 (3)
O1—C6—C7—O3	77.9 (6)	C12B—C13B—C14B—C15B	1 (4)
O1—C6—C7—C8	−45.0 (6)	C13A—C14A—C15A—C16A	−3 (3)
C5—C6—C7—O3	−40.7 (8)	C13B—C14B—C15B—C16B	−1 (5)
C5—C6—C7—C8	−163.7 (5)	C14A—C15A—C16A—C17A	3 (3)
O3—C7—C8—C9	−111.7 (7)	C14B—C15B—C16B—C17B	2 (4)
C6—C7—C8—C9	13.0 (9)	C15A—C16A—C17A—C12A	−0 (3)
C7—C8—C9—C10	−1.1 (11)	C15B—C16B—C17B—C12B	−4 (4)
C8—C9—C10—O1	20.8 (10)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3i	0.82	1.95	2.692 (8)	151
O3—H3···O2ii	0.82	1.89	2.614 (8)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3i	0.82	1.95	2.692 (8)	151
O3—H3⋯O2ii	0.82	1.89	2.614 (8)	147

Symmetry codes: (i) ; (ii) .