116003-78-2

Basic information

• Product Name: Methyl 2-azido-2-deoxy-4,6-O-(phenylmethylene)-α-D-mannopyranoside
• Synonyms: Methyl 2-azido-2-deoxy-4,6-O-(phenylmethylene)-α-D-mannopyranoside
• CAS NO: 116003-78-2
• Molecular Weight: 307.306
• Mol File: 116003-78-2.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: Methyl 2-azido-2-deoxy-4,6-O-(phenylmethylene)-α-D-mannopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2-azido-2-deoxy-4,6-O-(phenylmethylene)-α-D-mannopyranoside(116003-78-2)
• EPA Substance Registry System: Methyl 2-azido-2-deoxy-4,6-O-(phenylmethylene)-α-D-mannopyranoside(116003-78-2)

Safety Data

• Hazardous Substances Data: 116003-78-2(Hazardous Substances Data)

Upstream product

• 115945-97-6 methyl 3-O-acetyl-2-azido-4,6-O-benzylidene-2-deoxy-α-D-mannopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 115945-96-5 methyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(N-imidazolylsulfonyl)-α-D-altropyranoside 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 129217-24-9 4,6-O-benzylidene-1-O-methyl-2-O-trifluoromethylsulfonate-α-D-glucopyranoside 
• 116003-77-1 2-azido-2-deoxy-4,6-O-(phenylmethylene)methyl-α-D-altropyranoside 

Downstream Products

• 68733-20-0 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-α-D-mannopyranoside 
• 635292-85-2 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-β-D-mannopyranose 
• 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 
• 1644625-41-1 C₃₁H₄₀N₂O₈S 
• 1644625-40-0 C₂₈H₃₄N₂O₈S 
• 1644625-39-7 C₂₉H₃₆N₂O₈S 
• 1644625-38-6 C₃₅H₄₀N₂O₈S 

Relevant articles and documents

Synthesis of 1,2,3-triazolyl analog of Neisseria meningitidis A capsular polysaccharide

Towards constructing a stable, non-hydrolyzable linkage for Neisseria meningitidis type A (MenA) polysaccharide, the phosphate bridge of its (1→6)-linked 2-acetamido-2-deoxy-α-D-mannopyranosyl phosphate repeating unit was replaced by a triazolyl analog using Cu(I) catalyzed click reaction. The synthesis involved anomeric azidation of N-acetyl-D-mannosamine derivative from its acetate precursor using stoichiometric amount of FeCl3 and one-pot synthesis of precursors for di- and tri- triazolyl saccharides with an azidoethyl spacer at the reducing end for bioconjugation.

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.

Chemoenzymatic synthesis of CMP-N-acetyl-7-fluoro-7-deoxy-neuraminic acid

7-Fluoro sialic acid was prepared and activated as cytidine monophosphate (CMP) ester. The synthesis started with d-glucose, which was efficiently converted into N-acetyl-4-fluoro-4-deoxy-d-mannosamine. Aldolase catalyzed transformation yielded the corres