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Literature DB >> 30015496

Stereospecific Synthesis of the Saccharosamine-Rhamnose-Fucose Fragment Present in Saccharomicin B.

Abstract

A synthetic route has been developed for constructing the d-saccharosamine-l-rhamnose-d-fucose (Sac-Rha-Fuc) trisaccharide fragment present in the antibacterial natural product saccharomicin B. The Sac monosaccharide was synthesized through a modified nine step procedure starting from d-rhamnal in 23% overall yield. 1- O-TBS Sac donors were used to construct the β-linked Sac-Rha disaccharide. This disaccharide was coupled to a Fuc acceptor under BSP/Tf2O conditions to afford a trisaccharide properly functionalized for elaboration to saccharomicin B.

Entities: Chemical Disease Gene Species

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Year: 2018 PMID： 30015496 PMCID： PMC6094934 DOI： 10.1021/acs.orglett.8b02028

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

24 in total

1. Direct and stereoselective synthesis of beta-linked 2,6-deoxyoligosaccharides.

Authors: Hiroshi Tanaka; Atsushi Yoshizawa; Takashi Takahashi
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

2. Primary tert- and sec-allylamines via palladium-catalyzed hydroamination and allylic substitution with hydrazine and hydroxylamine derivatives.

Authors: Adam M Johns; Zhijian Liu; John F Hartwig
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

3. Reagent-Controlled Synthesis of the Branched Trisaccharide Fragment of the Antibiotic Saccharomicin B.

Authors: Sameh E Soliman; Clay S Bennett
Journal: Org Lett Date: 2018-05-23 Impact factor: 6.005

4. Synthesis of the saccharomicin fucose-aglycon conjugate and determination of absolute configuration.

Authors: Joseph M Pletcher; Frank E McDonald
Journal: Org Lett Date: 2005-10-13 Impact factor: 6.005

5. Mechanistic studies and methods to prevent aglycon transfer of thioglycosides.

Authors: Zhitao Li; Jeffrey C Gildersleeve
Journal: J Am Chem Soc Date: 2006-09-06 Impact factor: 15.419

6. Direct glycosylation of bioactive small molecules with glycosyl iodide and strained olefin as acid scavenger.

Authors: Xiangying Gu; Lin Chen; Xin Wang; Xiao Liu; Qidong You; Wenwei Xi; Li Gao; Guohua Chen; Yue-Lei Chen; Bing Xiong; Jingkang Shen
Journal: J Org Chem Date: 2014-02-07 Impact factor: 4.354

7. An Improved Approach to the Direct Construction of 2-Deoxy-β-Linked Sugars: Applications to Oligosaccharide Synthesis.

Authors: Dina Lloyd; Clay S Bennett
Journal: Chemistry Date: 2018-05-02 Impact factor: 5.236

8. 1-Benzenesulfinyl piperidine/trifluoromethanesulfonic anhydride: a potent combination of shelf-stable reagents for the low-temperature conversion of thioglycosides to glycosyl triflates and for the formation of diverse glycosidic linkages.

Authors: D Crich; M Smith
Journal: J Am Chem Soc Date: 2001-09-19 Impact factor: 15.419

9. Regioselectivity of rhodium nitrene insertion. Syntheses of protected glycals of l-daunosamine, d-saccharosamine, and l-ristosamine.

Authors: Kathlyn A Parker; Wonsuk Chang
Journal: Org Lett Date: 2005-04-28 Impact factor: 6.005

Stereospecific Synthesis of the Saccharosamine-Rhamnose-Fucose Fragment Present in Saccharomicin B.

1. Direct and stereoselective synthesis of beta-linked 2,6-deoxyoligosaccharides.

2. Primary tert- and sec-allylamines via palladium-catalyzed hydroamination and allylic substitution with hydrazine and hydroxylamine derivatives.

3. Reagent-Controlled Synthesis of the Branched Trisaccharide Fragment of the Antibiotic Saccharomicin B.

4. Synthesis of the saccharomicin fucose-aglycon conjugate and determination of absolute configuration.

5. Mechanistic studies and methods to prevent aglycon transfer of thioglycosides.

6. Direct glycosylation of bioactive small molecules with glycosyl iodide and strained olefin as acid scavenger.

7. An Improved Approach to the Direct Construction of 2-Deoxy-β-Linked Sugars: Applications to Oligosaccharide Synthesis.

8. 1-Benzenesulfinyl piperidine/trifluoromethanesulfonic anhydride: a potent combination of shelf-stable reagents for the low-temperature conversion of thioglycosides to glycosyl triflates and for the formation of diverse glycosidic linkages.

9. Regioselectivity of rhodium nitrene insertion. Syntheses of protected glycals of l-daunosamine, d-saccharosamine, and l-ristosamine.

10. Reagent controlled β-specific dehydrative glycosylation reactions with 2-deoxy-sugars.

1. Synthesis of the Non-Reducing Hexasaccharide Fragment of Saccharomicin B.

2. General Method for the Synthesis of α- or β-Deoxyaminoglycosides Bearing Basic Nitrogen.

3. Rapid de Novo Preparation of 2,6-Dideoxy Sugar Libraries through Gold-Catalyzed Homopropargyl Orthoester Cyclization.

Review 4. Glucose metabolism and glycosylation link the gut microbiota to autoimmune diseases.