103597-19-9

Upstream product

• 103597-18-8 methyl-2,3,4-tri-O-benzyl-7,7,8,8-tetradehydro-7,8-dideoxy-α-D-glycero-D-gluco-octopyranoside 
• 3536-96-7 vinylmagnesium chloride 
• 83051-88-1 methyl 6-aldehydo-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 3162-96-7 methyl 4,6-O-benzylidene-α-D-glucopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 63734-12-3 methyl 6-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside 
• 166592-73-0 methyl 2,3,4-tri-O-benzyl-6-O-(tert-butyldimethylsilyl)-α-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 
• 1826-67-1 vinyl magnesium bromide 

Downstream Products

• 177897-27-7 (S)-Hydroxy-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-acetaldehyde 
• 103597-25-7 methyl 6,7-di-O-acetyl-2,3,4-tri-O-benzyl-L-glycero-α-D-gluco-heptopyranoside 
• 103597-21-3 methyl 6,7-di-O-acetyl-2,3,4-tri-O-benzyl-D-glycero-α-D-gluco-heptopyranoside 
• 103597-24-6 methyl 2,3,4-tri-O-benzyl-L-glycero-α-D-gluco-heptopyranoside 
• 103597-20-2 methyl 2,3,4-tri-O-benzyl-D-glycero-α-D-gluco-heptopyranoside 
• 103597-32-6 (R)-1-((2R,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-2-trityloxy-ethanol 
• 103597-32-6 (S)-1-((2R,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-2-trityloxy-ethanol 
• 103597-31-5 Benzoic acid (S)-1-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-2-trityloxy-ethyl ester 
• 103597-26-8 Methanesulfonic acid (R)-1-((2S,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-2-trityloxy-ethyl ester 
• 103597-29-1 (2R,3R,4S,5R,6S)-2-((S)-1-Azido-2-trityloxy-ethyl)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran 
• 103597-28-0 Acetic acid (R)-2-methanesulfonyloxy-2-((2S,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-ethyl ester 
• 103597-30-4 Acetic acid (S)-2-azido-2-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-ethyl ester 
• 103597-27-9 Methanesulfonic acid (R)-2-hydroxy-1-((2S,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-ethyl ester 
• 1401562-88-6 C₄₀H₄₁F₃O₈ 

Relevant academic research and scientific papers

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.

Ring-closing metathesis as a new strategy for the C-C coupling of monosaccharide derivatives via silicon tethering

Suitable carbohydrate-derived terminal olefins have been coupled by ring-closing metathesis reaction following a silicon tethering strategy, generating very long contiguous chains of carbon atoms each equipped with specific stereochemistry and functionali

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

Preparation of sugar-derived α-acetoxy-aldehydes

A convenient method for conversion of sugar diols (2a-2d) into a-acetoxy-aldehydes: 5-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranos-6-ulose (5a), 5-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranos-6-ulose (5b), methyl 6-O-acetyl-2,3,4-tri-O-benzyl-D-glycero-α-D-gluco- and L-glycero-α-D-gluco-heptopyranosid-7-uloses (5c and 5d respectively) is presented. This involves the protection (as TBDMS ether) of the primary hydroxyl group, acetylation of the remaining secondary one and desilylation followed by a Swern oxidation. Partial migration of the acetyl group during desilylation (with Bu4NF) was observed for compound 4a and complete migration for 4f. α-Acetoxy-aldehydes 5a-5d were characterized as adducts with Ph3P = CH-CO2Me (12a-12d).

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

Synthesis of Methyl 2,3,4-tri-O-benzyl-D- and L-glycero-α-D-glucoheptopyranosides

Title compounds 8 and 17 have been synthesized from methyl 2,3,4-tri-O-benzyl-7,8-dideoxy-D- and L-glycero-α-D-gluco-oct-7-ynopyranosides (6 and 15 respectively) in three steps: hydrogenation of the triple bond, ozonolytic cleavage of the resulting double