103597-23-5

Basic information

• Product Name: methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-L-glycero-α-D-gluco-oct-7-ene-1,5-pyranoside
• CAS NO: 103597-23-5
• Molecular Weight: 490.596
• Mol File: 103597-23-5.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-L-glycero-α-D-gluco-oct-7-ene-1,5-pyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-L-glycero-α-D-gluco-oct-7-ene-1,5-pyranoside(103597-23-5)
• EPA Substance Registry System: methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-L-glycero-α-D-gluco-oct-7-ene-1,5-pyranoside(103597-23-5)

Safety Data

• Hazardous Substances Data: 103597-23-5(Hazardous Substances Data)

Upstream product

• 166592-73-0 methyl 2,3,4-tri-O-benzyl-6-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside 
• 63734-12-3 methyl 6-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 7177-79-9 methyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 3162-96-7 methyl 4,6-O-benzylidene-α-D-glucopyranoside 
• 3536-96-7 vinylmagnesium chloride 
• 83051-88-1 methyl 6-aldehydo-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 1826-67-1 vinyl magnesium bromide 
• 103597-22-4 methyl-2,3,4-tri-O-benzyl-7,7,8,8-tetradehydro-7,8-dideoxy-β-L-glycero-D-gluco-octopyranoside 

Downstream Products

• 103597-25-7 methyl 6,7-di-O-acetyl-2,3,4-tri-O-benzyl-L-glycero-α-D-gluco-heptopyranoside 
• 103597-24-6 methyl 2,3,4-tri-O-benzyl-L-glycero-α-D-gluco-heptopyranoside 
• 177897-16-4 (2S,3S)-3-Benzyloxy-3-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-propane-1,2-diol 
• 177897-21-1 Acetic acid (R)-2-oxo-1-((2S,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-ethyl ester 
• 286466-53-3 Diphenyl-bis-[(S)-1-((2S,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-allyloxy]-silane 
• 115520-86-0 methyl 2,3,4-tri-O-benzyl-D-threo-α-D-gluco-oct-1,5-pyranoside 
• 177897-29-9 (2R,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-((S)-1-benzyloxy-allyl)-6-methoxy-tetrahydro-pyran 

Relevant articles and documents

Construction of the octose 8-phosphate intermediate in lincomycin A biosynthesis: Characterization of the reactions catalyzed by LmbR and LmbN

Lincomycin A is a potent antimicrobial agent noted for its unusual C1 methylmercapto-substituted 8-carbon sugar. Despite its long clinical history for the treatment of Gram-positive infections, the biosynthesis of the C 8-sugar, methylthiolincosamide (MTL), is poorly understood. Here, we report our studies of the two initial enzymatic steps in the MTL biosynthetic pathway leading to the identification of d-erythro-d-gluco-octose 8-phosphate as a key intermediate. Our experiments demonstrate that this intermediate is formed via a transaldol reaction catalyzed by LmbR using d-fructose 6-phosphate or d-sedoheptulose 7-phosphate as the C3 donor and d-ribose 5-phosphate as the C5 acceptor. Subsequent 1,2-isomerization catalyzed by LmbN converts the resulting 2-keto C8-sugar (octulose 8-phosphate) to octose 8-phosphate. These results provide, for the first time, in vitro evidence for the biosynthetic origin of the C8 backbone of MTL.

Simple synthesis of D-erythro- and L-erythro-D-gluco-octoses

Synthesis of the previously unknown methyl 2,3,4-tri-O-benzyl-L-erythro-β-D-gluco-and D-erythro-α-D-gluco-oct-1,5-pyranosides (1 and 2) was accomplished on two independent routes via either cis-hydroxylation of stereoisomeric 6-C-vinyl-L-glycero-β-D-gluco

Chain-extension of carbohydrates. 5. Synthesis of the C-glycosyl amino acid moiety of miharamycins involving stereocontrolled ethynylation of methyl 2,3,4-tri-O-benzyl-α-D-gluco-hexodialdo-1,5-pyranoside

A multistep synthesis of the C-glycosyl amino acid moiety of miharamycins from methyl 2,3,4-tri-O-benzyl-α-D-gluco-hexodialdo-1,5-pyranoside (1) is described. The ethynyl group was employed as a synthetic equivalent of the carboxylic acid function. In the