172297-88-0

Basic information

• Product Name: methyl 2,3,6-tri-O-benzyl-4-deoxy-β-L-threo-hex-4-enopyranoside
• Synonyms: methyl 2,3,6-tri-O-benzyl-4-deoxy-β-L-threo-hex-4-enopyranoside
• CAS NO: 172297-88-0
• Molecular Weight: 446.543
• Mol File: 172297-88-0.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: methyl 2,3,6-tri-O-benzyl-4-deoxy-β-L-threo-hex-4-enopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2,3,6-tri-O-benzyl-4-deoxy-β-L-threo-hex-4-enopyranoside(172297-88-0)
• EPA Substance Registry System: methyl 2,3,6-tri-O-benzyl-4-deoxy-β-L-threo-hex-4-enopyranoside(172297-88-0)

Safety Data

• Hazardous Substances Data: 172297-88-0(Hazardous Substances Data)

Upstream product

• 432038-84-1 methyl 2,3,6-tri-O-benzyl-4-O-(1H-imidazol-1-ylsulfonyl)-α-D-galactopyranoside 
• 288-94-8 1H-tetrazole 
• 88713-85-3 methyl 4-azido-2,3,6-tri-O-benzyl-4-deoxy-α-D-galactopyranoside 
• 121-45-9 phosphorous acid trimethyl ester 
• 19488-48-3 methyl 2,3,6-tri-O-benzyl-α-D-galactopyranoside 
• 7189-69-7 N,N`-sulfuryldiimidazole 
• 192637-12-0 methyl 2,3,6-tri-O-benzyl-4-O-triflyl-α-D-(4-2H)glucopyranoside 
• 184898-72-4 methyl 2,3,6-tri-O-benzyl-4-O-triflyl-α-D-(4-2H)galactopyranoside 
• 917-54-4 methyllithium 
• 112260-57-8 methyl 2,3,6-tri-O-benzyl-α-D-glucopyranoside 

Relevant articles and documents

α-Hydrogen Elimination in Some Carbohydrate Triflates

In some carbohydrate triflates, treatment with MeLi (or BuLi) in ether caused α-hydrogen elimination initially, then the resulting carbanion is stabilized to give either C-methyl(or butyl)-hydroxy derivatives or unsaturated products.

A New reaction for the direct conversion of 4-azido-4-deoxy-D-galactoside into a 4-deoxy-D-erythro-hexos-3-ulose

A new one-step reaction has been developed for converting 4-azido-4-deoxy-D-galactoside into 4-deoxy-D-erythro-hexos-3-ulose by phosphoramidites and tetrazole. It is proposed that the new reaction proceeds via an intramolecular Staudinger reaction of the

Reactions of some 2- and 4-O-triflylglycopyranosides with MeLi, t-BuOK, and pyridine

As an extension of our previous work on secondary triflates of carbohydrates [El Nemr, A.; Tsuchiya, T. Tetrahedron Lett. 1995, 36, 7665-7668. El Nemr, A.; Tsuchiya, T.; Kobayashi, Y. Carbohydr. Res. 1996, 293, 31-59. El Nemr, A.; Tsuchiya, T. Carbohydr. Res. 1997, 301, 77-87. El Nemr, A.; Tsuchiya, T. Carbohydr. Res. 1997, 303, 267-281], the reaction modes of several methyl 2- and 4-O-triflyl-D-glycopyranosides with MeLi (strong base), t-BuOK (moderately strong base), and pyridine (weak base) have been studied. This paper describes the reactions of 3-O-benzyl-4,6-O-benzylidene-2-O-triflyl-D-gluco and -mannopyranosides with MeLi to give mainly the corresponding 2-C-methyl derivatives through α-elimination, with t-BuOK to give either the 2,3-unsaturated compounds through β-elimination or detriflyl 2-ols, and with hot pyridine to give the corresponding 2-pyridinium salts with inversion (except for the 2-O-triflyl-α-D-mannopyranoside (8)). 2,3,6-Tri-O-benzyl-4-O-triflyl-α-D-gluco and -mannopyranosides were also examined similarly.