Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 Direct C-glycosylation of organotrifluoroborates with glycosyl fluorides and its application to the total synthesis of (+)-varitriol.

Literature DB >> 21114334

Direct C-glycosylation of organotrifluoroborates with glycosyl fluorides and its application to the total synthesis of (+)-varitriol.

Jing Zeng¹, Seenuvasan Vedachalam, Shaohua Xiang, Xue-Wei Liu.

Abstract

A mild, stereoselective, and quick approach to accessing alkynyl and alkenyl C-glycosides via BF(3)·Et(2)O promoted coupling of organotrifluoroborates and glycosyl fluorides is reported. The application of this method was further demonstrated by the concise and efficient total synthesis of (+)-varitriol in only seven steps.

Entities: Chemical

Mesh：

Substances：

Year: 2010 PMID： 21114334 DOI： 10.1021/ol102473k

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

Keyword Cloud
Cited

14 in total

1. Macrocyclic bis-thioureas catalyze stereospecific glycosylation reactions.

Authors: Yongho Park; Kaid C Harper; Nadine Kuhl; Eugene E Kwan; Richard Y Liu; Eric N Jacobsen
Journal: Science Date: 2017-01-13 Impact factor: 47.728

2. Facile Synthesis of Sugar Lactols via Bromine-Mediated Oxidation of Thioglycosides.

Authors: Shuai Meng; Bishwa Raj Bhetuwal; Padam P Acharya; Jianglong Zhu
Journal: J Carbohydr Chem Date: 2019-03-20 Impact factor: 1.667

3. Diastereoselective, Zinc-Catalyzed Alkynylation of α-Bromo Oxocarbenium Ions.

Authors: Tatsiana Haidzinskaya; Hilary A Kerchner; Jixin Liu; Mary P Watson
Journal: Org Lett Date: 2015-07-21 Impact factor: 6.005

4. Identification and Characterization of Enzymes Catalyzing Pyrazolopyrimidine Formation in the Biosynthesis of Formycin A.

Authors: Yeonjin Ko; Shao-An Wang; Yasushi Ogasawara; Mark W Ruszczycky; Hung-Wen Liu
Journal: Org Lett Date: 2017-02-24 Impact factor: 6.005

Direct C-glycosylation of organotrifluoroborates with glycosyl fluorides and its application to the total synthesis of (+)-varitriol.

1. Macrocyclic bis-thioureas catalyze stereospecific glycosylation reactions.

2. Facile Synthesis of Sugar Lactols via Bromine-Mediated Oxidation of Thioglycosides.

3. Diastereoselective, Zinc-Catalyzed Alkynylation of α-Bromo Oxocarbenium Ions.

4. Identification and Characterization of Enzymes Catalyzing Pyrazolopyrimidine Formation in the Biosynthesis of Formycin A.

5. Blue Light Photocatalytic Glycosylation without Electrophilic Additives.

6. Synthesis of a C-phosphonate mimic of maltose-1-phosphate and inhibition studies on Mycobacterium tuberculosis GlgE.

7. A Highly Efficient Glycosidation of Glycosyl Chlorides by Using Cooperative Silver(I) Oxide-Triflic Acid Catalysis.

8. β-D-Arabinosyl 1-C-sulfonic acid^.

9. Diastereoselective Synthesis of Aryl C-Glycosides from Glycosyl Esters via C-O Bond Homolysis.

10. Mild Cu(OTf)₂-Mediated C-Glycosylation with Chelation-Assisted Picolinate as a Leaving Group.