99212-41-6

Basic information

• Product Name: methyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside
• Synonyms: methyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside
• CAS NO: 99212-41-6
• Molecular Weight: 414.455
• Mol File: 99212-41-6.mol

Chemical Properties

• CAS DataBase Reference: methyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside(99212-41-6)
• EPA Substance Registry System: methyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside(99212-41-6)

Safety Data

• Hazardous Substances Data: 99212-41-6(Hazardous Substances Data)

Upstream product

• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 76375-66-1 methyl 2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 75-36-5 acetyl chloride 
• 108-24-7 acetic anhydride 
• 4288-93-1 methyl 4,6-O-benzylidene-α-D-galactopyranoside 

Downstream Products

• 99152-62-2 Methyl-3-O-acetyl-2-O-benzyl-4,6-di-O-mesyl-α-D-glucopyranosid 
• 99152-63-3 Methyl-3-O-acetyl-2-O-benzyl-6-desoxy-6-iodo-4-O-mesyl-α-D-glucopyranosid 
• 99152-67-7 Methyl-4-azido-2-O-benzyl-3-O-chloracetyl-4,6-didesoxy-α-D-galactopyranosid 
• 99152-64-4 Methyl-3-O-acetyl-2-O-benzyl-6-desoxy-4-O-mesyl-α-D-glucopyranosid 
• 99152-65-5 Methyl-3-O-acetyl-4-azido-2-O-benzyl-4,6-didesoxy-α-D-galactopyranosid 
• 99152-66-6 Methyl-4-azido-2-O-benzyl-4,6-didesoxy-α-D-galactopyranosid 
• 294178-45-3 Phosphoric acid (2R,3R,4S,6R)-4-azido-3-benzyloxy-6-methyl-tetrahydro-pyran-2-yl ester dibenzyl ester 
• 294178-40-8 Acetic acid (2S,3R,4R,5R,6R)-3-benzyloxy-5-chloro-6-chloromethyl-2-methoxy-tetrahydro-pyran-4-yl ester 
• 294178-41-9 Acetic acid (2S,3R,4S,6R)-3-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yl ester 
• 294178-43-1 (2S,3R,4S,6R)-4-Azido-3-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran 
• 451505-76-3 (2S,3R,4S,6R)-3-Benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-ol 
• 294178-42-0 (2S,3R,4R,6R)-3-Benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-ol 
• 72212-12-5 (2S,3S,6R)-3-Benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-one 
• 203717-53-7 methyl 2,6-di-O-benzyl-3-O-acetyl-α-D-glucopyranoside 

Relevant articles and documents

Synthetic studies on the carbohydrate moiety of amipurimycin

The carbohydrate core of amipurimycin in its fully acetylated form was synthesized in 24 steps starting from commercially available methyl 4,6-O-benzylidene-α-D-glucopyranoside to give an overall yield of 1.5%. The late-stage intermediates involved were suitable for total synthesis of amipurimycin. It was further discovered that the branches and the protecting groups on the sugar rings of involved intermediates had a significant influence on their conformations, which in turn resulted in new and interesting cyclization reactions. Copyright Taylor & Francis Group, LLC.

DesVI: A new member of the sugar N,N-dimethyltransferase family involved in the biosynthesis of desosamine

Purification and characterization of a new enzyme belonging to the amino sugar N,N-dimethyltransferase family has been achieved. DesVI catalyzes the successive transfer of two methyl groups in the biosynthetic pathway of desosamine (see scheme), an unusua

Synthesis, NMR spectroscopy and conformational studies of the four anomeric methyl glycosides of the trisaccharide D-Glcp-(1→3)-[D-Glcp-(1→4)]-α-D-Glcp

The four anomeric methyl glycosides of the vicinally disubstituted trisaccharide D-Glcp-(1→3)-[D-Glcp-(1→4)]-α-D-Glcp have been synthesized using silver trifluoromethanesulfonate mediated glycosylations. The 1H and 13C NMR resonances have been assigned and used for extraction of glycosylation shifts, i.e. the differences between chemical shifts for signals from the trisaccharides and those of the respective monomers, as well as those derived by addition of the glycosylation shifts for each disaccharide element. Glycosylation shifts are up to 0.5 ppm for proton and 10 ppm for carbon. Deviations from additivity are -0.2-0.1 ppm for proton and -4.5-2.3 ppm for carbon, usually confined to the atoms at the linkage positions. The conformational space spanned for the trisaccharides, and the constituent disaccharides, has been investigated by Metropolis Monte Carlo simulations using the HSEA force field. The α-linked glucosyl groups show larger conformational changes with multiple energy minima, whereas the β-linked glucosyl groups have a single energy minimum, close to that identified for the constituent disaccharide.

Synthesis and NMR studies of methyl 3-O-[(R)- and (S)-1-carboxyethyl]-α-D-gluco-, galacto- and manno- pyranosides

The title compounds were prepared by condensation of a suitably protected monosaccharide and (R)- or (S)-2-chloropropionic acid followed by removal of the protecting groups. Characterisation by 1H and 13C NMR spectroscopy and NOE difference experiments revealed both chemical shift and enhancement differences between the diastereomers which could be used in determination of the absolute configuration of the 1-carboxyethyl group. Copyright (C) 1998 Elsevier Science Ltd.

ALKYLATION OF METHYL 4,6-O-BENZYLIDENE-α-D-GALACTOPYRANOSIDE

The partial alkylation of methyl 4,6-benzylidene-α-D-galactopyranoside in dimethylformamide and dimethyl sulfoxide in the presence of barium oxide and hydroxide is described.It has been shown that methylation and benzylation lead predominantly to the 3-al