Fluorination reactions at C-4 of methyl 2-O-benzyl-3,6-dideoxyhexopyranosides with diethylaminosulfur trifluoride (DAST) and with tris(dimethylamino)sulfonium difluorotrimethylsilicate (TASF)

DOI: 10.1248/cpb.39.1088

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 1088 - 1090 (1991)

Update date:2022-07-29

Topics:

Authors:

Mori Mori

Morishima

Read Full Text PDF DownLoad Join now for total 90,000,000 free articles

Article abstract of DOI:10.1248/cpb.39.1088

Fluorination at C-4 of methyl 2-O-benzyl-3,6-dideoxy-α-D-ribo- and α-D-arabino-hexopyranosides (1 and 5) using diethylaminosulfur trifluoride (DAST) proceeded with exclusive retention of configuration. But treating the triflates of 1 and 5 with tris(dimethylamino)sulfonium difluorotrimethylsilicate (TASF) afforded mostly the configurationally inverted fluorides.

Full text of DOI:10.1248/cpb.39.1088

NII-Electronic Library Service

Products guided by the article

Product name:(2S,3S,6R)-3-Benzyloxy-2-methoxy-6-methyl-3,6-dihydro-2H-pyran

Cas No:136087-22-4

R&D Labs maybe for 136087-22-4

JiangXi Keyuan Biopharma Co., LTD.

Contact:+86-563-6833666

Address:Guangde Fine Chemical Zone, Anhui Province, China
SYN Pharma Co., Ltd

Contact:86-21 60347964

Address:No.1304, West Meilong Road, Minhang District, Shanghai, China
Chengdu Herbpurify Co., Ltd

website:http://www.herbpurify.com

Contact:0086-028-85249238

Address:Room709-C1,Incubator Building, Tianfu Life Science Park No.88,Keyuan Road,Gaoxin district,Chengdu City,Sichuan Prov,China
Jintan City Mego Chemical Co., Ltd

Contact:+86-0519-82814387

Address:23# Dengguan Town, Jintan, Jiangsu Province, China
HAINAN JINYING IMPORT AND EXPORT CO. LTD

Contact:+86-898-32875423

Address:A SECTION 19TH FL, TIMES SQUARE, NO.2 GUO MAO AVENUE HAIKOU, HAINAN, P. R. OF CHINA

Relevant to this article

Accessing lipophilic ligands in dendrimer-based amphiphilic supramolecular assemblies for protein-induced disassembly

Doi:10.1002/chem.201102727
(2012)
Titanocene(II)-promoted cross-coupling of unsaturated compounds

Doi:10.1002/ejoc.200500976
(2006)
Development of a Large-Scale Route to Glecaprevir: Synthesis of the Macrocycle via Intramolecular Etherification

Doi:10.1021/acs.oprd.0c00244
(2020)
Effects of Steric Congestion on Photochemistry: Enol Ether Formation from α-Mesityl Ketones

Doi:10.1021/ja00210a057
(1988)
Synthesis of chiral α-ethylphenylamine salts of tartaric acid and novel application to cyanosilylation of prochiral ketones

Doi:10.1007/s11164-010-0132-7
(2010)
Synthesis of pyrrolophenanthridone alkaloid kalbretorine from indolecarboxylic acids via hypervalent iodine(III) mediated halodecarboxylation and reduction

Doi:10.1016/j.tetlet.2012.01.132
(2012)

Article Doi