676342-69-1

Basic information

• Product Name: 1,6-anhydro-2-O-{6-O-acetyl-2,4-di-O-benzoyl-3-O-[(p-nitrophenyl)formyl]-α-D-mannopyranosyl}-3,4-di-O-benzoyl-β-L-gulopyranoside
• Synonyms: 1,6-anhydro-2-O-{6-O-acetyl-2,4-di-O-benzoyl-3-O-[(p-nitrophenyl)formyl]-α-D-mannopyranosyl}-3,4-di-O-benzoyl-β-L-gulopyranoside
• CAS NO: 676342-69-1
• Molecular Weight: 947.86
• Mol File: 676342-69-1.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 1,6-anhydro-2-O-{6-O-acetyl-2,4-di-O-benzoyl-3-O-[(p-nitrophenyl)formyl]-α-D-mannopyranosyl}-3,4-di-O-benzoyl-β-L-gulopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 1,6-anhydro-2-O-{6-O-acetyl-2,4-di-O-benzoyl-3-O-[(p-nitrophenyl)formyl]-α-D-mannopyranosyl}-3,4-di-O-benzoyl-β-L-gulopyranoside(676342-69-1)
• EPA Substance Registry System: 1,6-anhydro-2-O-{6-O-acetyl-2,4-di-O-benzoyl-3-O-[(p-nitrophenyl)formyl]-α-D-mannopyranosyl}-3,4-di-O-benzoyl-β-L-gulopyranoside(676342-69-1)

Safety Data

• Hazardous Substances Data: 676342-69-1(Hazardous Substances Data)

Upstream product

• 676342-62-4 1,6-anhydro-3,4-di-O-benzoyl-β-L-gulopyranose 
• 676342-64-6 1,6-anhydro-2,4-di-O-benzoyl-β-D-mannopyranose 
• 676342-61-3 1,6-anhydro-3,4-di-O-benzoyl-2-O-trifluoromethanesulfonyl-β-L-idopyranose 
• 14168-65-1 mannosan 
• 7693-46-1 4-Nitrophenyl chloroformate 
• 60619-47-8 1,6-anhydro-β-L-idopyranose 
• 54769-36-7 N-benzoyloxybenzotriazole 
• 87357-54-8 6-deoxy-1,2:3,5-di-O-isopropylidene-α-D-xylo-hex-5-enofuranose 
• 81562-09-6 6-hydroxy-1,2:3,5-di-O-isopropylidene-α-D-glucofuranoside 

Downstream Products

• 676342-70-4 6-O-acetyl-2-O-{6-O-acetyl-2,4-di-O-benzoyl-3-O-[(p-nitrophenyl)formyl]-α-D-mannopyranosyl}-3,4-di-O-benzoyl-L-gulopyranosyl acetate 

Relevant articles and documents

From D-Glucose to Biologically Potent L-Hexose Derivatives: Synthesis of α-L-Iduronidase Fluorogenic Detector and the Disaccharide Moieties of Bleomycin A2 and Heparan Sulfate

A novel and convenient route for the synthesis of biologically potent and rare L-hexose derivatives from D-glucose is described. Conversion of diacetone-α-D-glucose (14) into 1,2:3,5-di-O-isopropylidene-β -L-idofuranose (19) was efficiently carried out in two steps. Orthogonal isopropylidene rearrangement of compound 19 led to 1,2:5,6-di-O-isopropylidene-β-L-idofuranose (27), which underwent regioselective epimerization at the C3 position to give the L-talo- and 3-functionalized L-idofuranosyl derivatives. Hydrolysis of compound 19 under acidic conditions furnished 1,6-anhydro-β-L-idopyranose (35) in excellent yield, which was successfully transformed into the corresponding L-allo, L-altro, L-gulo, and L-ido derivatives via regioselective benzylation, benzoylation, triflation and nucleophilic substitution as the key steps. Applications of these 1,6-anhydro-β-L-hexopyranoses as valuable building blocks to the syntheses of 4-methylcoumarin-7-yl-α-L-iduronic acid and the disaccharide moieties of bleomycin A2 as well as heparan sulfate are highlighted.