142789-96-6

Basic information

• Product Name: 1,2-O-anhydro-3-O-benzyl-4,6-O-benzylidene-5a-carba-β-D-mannopyranose
• Synonyms: 1,2-O-anhydro-3-O-benzyl-4,6-O-benzylidene-5a-carba-β-D-mannopyranose
• CAS NO: 142789-96-6
• Molecular Weight: 338.403
• Mol File: 142789-96-6.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 1,2-O-anhydro-3-O-benzyl-4,6-O-benzylidene-5a-carba-β-D-mannopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-O-anhydro-3-O-benzyl-4,6-O-benzylidene-5a-carba-β-D-mannopyranose(142789-96-6)
• EPA Substance Registry System: 1,2-O-anhydro-3-O-benzyl-4,6-O-benzylidene-5a-carba-β-D-mannopyranose(142789-96-6)

Safety Data

• Hazardous Substances Data: 142789-96-6(Hazardous Substances Data)

Upstream product

• 143058-81-5 (1R)-(1,3/2)-3-hydroxymethyl-5-cyclohexene-1,2-diol 
• 108867-01-2 (1S)-(-)-(1,3/2)-2,3-diacetoxy-4-cyclohexene-1-carboxylic acid 
• 100-44-7 benzyl chloride 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 142789-89-7 (1R,3R,6R,10S)-10-hydroxy-3-phenyl-2,4-dioxabicyclo<4.4.0>dec-8-ene 
• 100-39-0 benzyl bromide 

Downstream Products

• 331273-42-8 Methyl (3-O-benzyl-4,6-O-benzylidene-5a-carba-α-D-mannapyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 504422-58-6 dodecyl 2,3,4,6-tetra-O-acetyl-3-O-benzyl-5a-carba-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 
• 504422-53-1 dodecyl 3-O-benzyl-4,6-O-benzylidene-5a-carba-β-D-arabino-hex-ulopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 504422-52-0 dodecyl 3-O-benzyl-4,6-O-benzylidene-5a-carba-α-D-arabino-hex-ulopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 504422-54-2 dodecyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-5a-carba-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 504422-51-9 dodecyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-5a-carba-α-D-mannopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 504422-57-5 dodecyl 2,4,6-tri-O-acetyl-3-O-benzyl-5a-carba-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 504422-56-4 dodecyl 2-O-acetyl-3-O-benzyl-4,6-di-O-methanesulfonyl-5a-carba-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 148253-85-4 (2R,3S,4S,5S,6R)-2-Hydroxymethyl-6-((1R,2S,3R,4R,6S)-2,3,6-trihydroxy-4-hydroxymethyl-cyclohexyloxy)-tetrahydro-pyran-3,4,5-triol 
• 142967-90-6 2-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-5a-carba-α-D-mannopyranose octa-N,O-acetate 
• 142968-03-4 2-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-1,3-di-O-benzyl-4,6-O-benzylidene-5a-carba-α-D-mannopyranose 
• 142968-02-3 1,3-di-O-benzyl-4,6-O-benzylidene-5a-carba-2-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-α-D-mannopyranose 
• 142968-01-2 1,3-di-O-benzyl-4,6-O-benzylidene-5a-carba-2-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-α-D-mannopyranose 
• 142790-00-9 2-acetamido-1-azido-3-O-benzyl-4,6-O-benzylidene-5a-carba-1,2-dideoxy-Β-D-glucopyranose 

Relevant articles and documents

Synthesis of an ether-linked alkyl 5a-carba-β-D-glucoside, a 5a-carba-β-D-galactoside, a 2-acetamido-2-deoxy-5a-carba-β-D-glucoside, and an alkyl 5a′-carba-β-lactoside

For the purpose of providing biologically stable building blocks for the biocombinatorial synthesis using a living cell, some ether-linked alkyl 5a-carba-β-D-glycoside primers were prepared. The key step of the synthesis was coupling of 1-bromo-n-alkanes with the 1-OH unprotected derivatives of 5a-carba-sugar analogues of D-glucose, D-galactose, and 2-acetamido-2-deoxy-D-glucose (N-acetyl-D-glucosamine), in DMF in the presence of sodium hydride. Alternatively, alkyl carba-lactoside was synthesized by incorporation of a 5a-carba-β-D-galactose residue into the 4-position of dodecyl β-D-glucopyranoside. A strong and specific inhibition of β-galactosidase (Ki 0.67 μM, bovine liver) was found for dodecyl 5a-carba-β-D-galactopyranoside.