68567-54-4

Basic information

• Product Name: 1,2-di-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside
• Synonyms: 1,2-di-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside
• CAS NO: 68567-54-4
• Molecular Weight: 534.606
• Mol File: 68567-54-4.mol
• Article Data: 28

Chemical Properties

• CAS DataBase Reference: 1,2-di-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-di-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside(68567-54-4)
• EPA Substance Registry System: 1,2-di-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside(68567-54-4)

Safety Data

• Hazardous Substances Data: 68567-54-4(Hazardous Substances Data)

Upstream product

• 53270-12-5 1,2-O-(1-ethoxyethylene) 3,4,6-tri-O-benzyl-1-thio-α-D-glucopyranose 
• 64-19-7 acetic acid 
• 20672-66-6 3,4,6-tri-O-benzyl-D-glucopyranose 
• 75-36-5 acetyl chloride 
• 20672-66-6 3,4,6-tri-O-benzyl-D-mannopyranose 
• 108-24-7 acetic anhydride 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 79218-68-1 2-O-acetyl-3,4,6-tri-O-benzyl-D-glucopyranose 
• 51532-75-3 3,4,6-tri-O-benzyl-1,2-O-(1-methoxyethylidene)-α-D-glucopyranose 
• 3254-16-8 3,4,6-tri-O-acetyl-[1,2-O-(1-methoxyethylidene)]-α-D-glucopyranose 
• 158852-31-4 3,4,6-tri-O-benzyl-1,2-O-(exo-ethoxyethylidene)-α-D-glucopyranose 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 125135-29-7 3,4,6-tri-O-benzyl-[1,2-O-(1-methoxyethylidene)]-α-D-glucopyranoside 

Downstream Products

• 79218-68-1 2-O-acetyl-3,4,6-tri-O-benzyl-D-glucopyranose 
• 79317-18-3 1-O-allyl-2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside 
• 55659-53-5 1,2-di-O-acetyl-3,4,6-tri-O-benzyl-d-glucopyranose 
• 869207-81-8 p-(methoxycarbonyl)phenyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside 
• 869207-84-1 p-(methoxycarbonyl)phenyl 3,4,6-tri-O-benzyl-D-mannopyranosyl-α-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside 
• 869207-83-0 p-(methoxycarbonyl)phenyl 2-O-acetyl-3,4,6-tri-O-benzyl-D-mannopyranosyl-α-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside 
• 1011529-36-4 (2-methyl-5-tert-butylphenyl) 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 
• 220734-61-2 4-methoxyphenyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside 
• 152871-96-0 phenyl 1-deoxy-2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 
• 1220779-31-6 C₅₆H₅₄O₉ 
• 1380315-30-9 C₅₉H₆₃N₃O₁₁ 
• 1380315-29-6 C₅₉H₆₃N₃O₁₁ 
• 1380315-26-3 C₅₄H₅₇N₃O₁₂ 

Relevant articles and documents

Synthetic trisaccharides reveal discrimination of: Endo -glycosidic linkages by exo -acting α-1,2-mannosidases in the endoplasmic reticulum

A tri-antennary Man9GlcNAc2 glycan on the surface of endoplasmic reticulum (ER) glycoproteins functions as a glycoprotein secretion or degradation signal after regioselective cleavage of the terminal α-1,2-mannose residue of each branch. Four α-1,2-mannos

Synthesis and binding affinity analysis of α1-2- and α1-6-O/S-linked dimannosides for the elucidation of sulfur in glycosidic bonds using quartz crystal microbalance sensors

The role of sulfur in glycosidic bonds has been evaluated using quartz crystal microbalance methodology. Synthetic routes towards α1-2- and α1-6-linked dimannosides with S- or O-glycosidic bonds have been developed, and the recognition properties assessed in competition binding assays with the cognate lectin concanavalin A. Mannose-presenting QCM sensors were produced using photoinitiated, nitrene-mediated immobilization methods, and the subsequent binding study was performed in an automated flow-through instrumentation, and correlated with data from isothermal titration calorimetry. The recorded Kd-values corresponded well with reported binding affinities for the O-linked dimannosides with affinities for the α1-2-linked dimannosides in the lower micromolar range. The S-linked analogs showed slightly disparate effects, where the α1-6-linked analog showed weaker affinity than the O-linked dimannoside, as well as positive apparent cooperativity, whereas the α1-2-analog displayed very similar binding compared to the O-linked structure.

Armed-disarmed effect on the stability of cysteine thioglucosides

Thioglucosides of cysteine show variable stability depending on the nature of the protecting groups on the glycosyl donor. Armed protecting groups (benzyl) lead to products that decompose readily while disarmed protecting groups (acetyl) lead to more stable products. Since this armed/disarmed effect of the protecting group on the stability of the thioglucosides is more pronounced for cysteine with an unprotected carboxylic group, the proposed mechanism is that decomposition is initiated by an intramolecular protonation of glycosyl sulfide and subsequent displacement of the sulfide by adventitious nucleophiles.