129217-24-9

Basic information

• Product Name: 4,6-O-benzylidene-1-O-methyl-2-O-trifluoromethylsulfonate-α-D-glucopyranoside
• Synonyms: 4,6-O-benzylidene-1-O-methyl-2-O-trifluoromethylsulfonate-α-D-glucopyranoside
• CAS NO: 129217-24-9
• Molecular Weight: 414.356
• Mol File: 129217-24-9.mol
• Article Data: 16

Chemical Properties

• CAS DataBase Reference: 4,6-O-benzylidene-1-O-methyl-2-O-trifluoromethylsulfonate-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 4,6-O-benzylidene-1-O-methyl-2-O-trifluoromethylsulfonate-α-D-glucopyranoside(129217-24-9)
• EPA Substance Registry System: 4,6-O-benzylidene-1-O-methyl-2-O-trifluoromethylsulfonate-α-D-glucopyranoside(129217-24-9)

Safety Data

• Hazardous Substances Data: 129217-24-9(Hazardous Substances Data)

Upstream product

• 421-83-0 trifluoromethane sulfonyl chloride 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 97-30-3 methyl-alpha-D-glucopyranoside 

Downstream Products

• 144607-21-6 methyl 2,3-di-S,O-acetyl-4,6-O-(phenylmethylene)-2-thio-α-D-mannopyranoside 
• 129217-25-0 methyl 3-O-(benzoylcarbamyl)-4,6-O-(phenylmethylene)-2-O-<(trifluoromethyl)sulfonyl>-α-D-glucopyranoside 
• 68733-20-0 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-α-D-mannopyranoside 
• 6752-48-3 methyl 4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 
• 1621188-44-0 methyl 2,3,4-tri-O-benzyl-6-O-(4,6-O-benzylidene-3-O-triisopropylsilyl-2-deoxy-α-D-erythro-hexapyranosyl)-α-D-glucopyranoside 
• 1621188-45-1 methyl 2,3,4-tri-O-benzyl-6-O-(4,6-O-benzylidene-3-O-triisopropylsilyl-2-deoxy-β-D-erythro-hexapyranosyl)-α-D-glucopyranoside 
• 1644625-34-2 C₂₇H₃₄N₂O₈ 
• 1644625-33-1 C₂₄H₃₆N₂O₈ 
• 1644625-32-0 C₂₁H₃₀N₂O₈ 
• 1644625-31-9 C₂₂H₃₂N₂O₈ 
• 1644625-30-8 C₂₈H₃₆N₂O₈ 
• 1644625-29-5 C₂₇H₃₄N₂O₈ 
• 1644625-28-4 C₂₅H₃₈N₂O₈ 
• 1644625-42-2 C₃₄H₃₈N₂O₈S 

Relevant articles and documents

Synthesis of 2-azido-2-deoxy- and 2-acetamido-2-deoxy-D-manno derivatives as versatile building blocks

Reported herein is the synthesis of a number of building blocks of 2-amino-2-deoxy-D-mannose from common D-glucose precursors.

A robust synthesis of N-glycolyl muramyl dipeptide via azidonitration/reduction

A novel synthetic route leading to N-glycolyl muramyl dipeptide (MDP), a bacterial glycopeptide of particular interest in studies of nucleotide-binding oligomerization domain-containing protein 2 (NOD2), is described. The synthetic strategy hinges on the alkylation of benzylidene-protected glucal with 2-bromopropionic acid and thus circumvents a challenging and non-reproducible SN2 step at the C-3 position of glucosamine derivatives. The subsequent sequence includes an azidonitration and an unusual azide reduction/acylation step via an aza ylide/oxaphospholidine intermediate. This approach generates a protected N-glycolyl MDP that can be either subjected to a one-step global deprotection or differentially deprotected to obtain further derivatives.

Modular hydroxyamide and thioamide pyranoside-based ligand library from the sugar pool: New class of ligands for asymmetric transfer hydrogenation of ketones

A large library of pyranoside-based hydroxyamide and thioamide ligands has been synthesized for asymmetric transfer hydrogenation in an attempt to expand the scope of the substrates to cover a broader range of challenging heteroaromatic and aryl/fluoroalkyl ketones. These ligands have the advantage that they are prepared from commercial D-glucose, D-glucosamine and α-amino acids, inexpensive natural chiral feedstocks. By carefully selecting the ligand components (substituents/configurations at the amide/thioamide moiety, the position of amide/thioamide group and the configuration at C-2), we found that pyranoside-based thioamide ligands provided excellent enantioselectivities (in the best cases, ees of >99% were achieved) in a broad range of ketones, including the less studied heteroaromatics and challenging aryl/fluoroalkyls. Note that both enantiomers of the reduction products can be obtained with excellent enantioselectivities by simply changing the absolute configuration of the thioamide substituent.