23397-65-1

Basic information

• Product Name: Methyl 2,3:5,6-di-O-benzylidene-α-D-mannofuranoside
• Synonyms: Methyl 2,3:5,6-di-O-benzylidene-α-D-mannofuranoside
• CAS NO: 23397-65-1
• Molecular Weight: 370.402
• Mol File: 23397-65-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Methyl 2,3:5,6-di-O-benzylidene-α-D-mannofuranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2,3:5,6-di-O-benzylidene-α-D-mannofuranoside(23397-65-1)
• EPA Substance Registry System: Methyl 2,3:5,6-di-O-benzylidene-α-D-mannofuranoside(23397-65-1)

Safety Data

• Hazardous Substances Data: 23397-65-1(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 530-26-7 D-Mannose 
• 1125-88-8 benzaldehyde dimethyl acetal 

Downstream Products

• 402758-84-3 methyl 2-O-benzyl-5-O-(tert-butyldiphenyl)silyl-α-D-arabinofuranoside 
• 76760-20-8 methyl-2,5-di-O-benzoyl-3,6-didesoxy-α-D-arabino-hexofuranoside 

Relevant articles and documents

Total synthesis of (+)-epiquinamide and (?)-epiepiquinamide from D-mannose

The total synthesis of (+)-epiquinamide and (?)-epiepiquinamide has been achieved starting from a 3,5-dihydroxyfuranoside synthon derived from D-mannose. The methods featured Bernet-Vasella reaction followed by Horner-Wadsworth-Emmons (HWE) reaction to provide a new chiral building block diene as the key steps. The bicyclic framework of this quinolizidine was constructed by using ring-closing metathesis, selective reduction of ester and intramolecular nucleophilic substitution-cyclization.

OUVERTURE PAR LE N-BROMOSUCCINIMIDE DES ACETALS BENZYLIDENIQUES DE METHYL-HEXOSIDES DE CONFIGURATION MANNO ET SYNTHESE DE LA N-ACETYL-L-MYCOSAMINE

Methyl 2,3:5,6-di-O-benzylidene-α-D-mannofuranoside and methyl 2,3-O-benzylidene-α-L-rhamnofuranoside were prepared according to a new procedure by simultaneous glycosidation and acetalation of D-mannose and L-rhamnose.Treatment of these compounds and of 1,6-anhydro-2,3-O-benzylidene-D-mannose with N-bromosuccinimide gave exclusively the 3-bromo compounds by regiospecific opening of the acetal ring.Thus, starting from rhamnose, N-acetyl-L-mycosamine (3-amino-3,6-dideoxy-L-mannose) was prepared in seven steps with a 32percent overall yield.