61243-00-3

Basic information

• Product Name: methyl 4-O-benzoyl-2,3,6-trideoxy-α-D-erythro-hex-2-enopyranoside
• Synonyms: methyl 4-O-benzoyl-2,3,6-trideoxy-α-D-erythro-hex-2-enopyranoside
• CAS NO: 61243-00-3
• Molecular Weight: 248.279
• Mol File: 61243-00-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: methyl 4-O-benzoyl-2,3,6-trideoxy-α-D-erythro-hex-2-enopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4-O-benzoyl-2,3,6-trideoxy-α-D-erythro-hex-2-enopyranoside(61243-00-3)
• EPA Substance Registry System: methyl 4-O-benzoyl-2,3,6-trideoxy-α-D-erythro-hex-2-enopyranoside(61243-00-3)

Safety Data

• Hazardous Substances Data: 61243-00-3(Hazardous Substances Data)

Upstream product

• 10368-81-7 methyl 4-O-benzoyl-6-bromo-6-deoxy-α-D-glucopyranoside 
• 65222-69-7 Methyl-2-O-benzoyl-3,4,6-tridesoxy-α-D-threo-hex-enopyranosid 
• 100164-72-5 Methyl-3,4,6-tridesoxy-α-D-erythro-hex-3-enopyranosid 
• 100164-73-6 Methyl-3,4,6-tridesoxy-α-D-threo-hex-3-enopyranosid 
• 65-85-0 benzoic acid 
• 79774-54-2 methyl 4-O-benzoyl-6-deoxy-α-D-glucopyranoside 
• 33647-82-4 methyl 2,3,6-trideoxy-α-DL-glycero-hex-2-enopyranosid-4-ulose 
• 26922-36-1 methyl 2,3,6-trideoxy-α-DL-erythro-hex-2-enopyranoside 
• 33647-67-5 1-(2,5-dimethoxy-2,5-dihydrofuran-2-yl)ethanol from 2-Acetylfuran 
• 1192-62-7 1-(2-furyl)-1-ethanone 
• 4208-64-4 1-(2-furyl)ethanol 
• 532-32-1 sodium benzoate 
• 40246-39-7 methyl 2,3,6-trideoxy-4-O-methylsulphonyl-α-DL-erythro-hex-2-enopyranoside 
• 201405-19-8 methyl 4-O-acetyl-2,3,6-trideoxy-α,β-L-erythro-hex-2-enopyranoside 

Relevant articles and documents

Total synthesis of the postulated structure of fulicineroside

A total synthesis of the proposed structures of fulicineroside and its aglycone fulicinerine is reported. The tetrasubstituted dibenzofuran substructure was accessible either through a Pd-mediated ortho-metalation or by an Ir-catalyzed meta-borylation. The synthesis of the β,β,α- linked trisaccharide consisting of D-olivose, L-rhodinose, and L-rhamnose was challenged by the unprecedented β-linked rhodinose. A Pd-catalyzed β-selective glycosylation of a 4-epi-rhodinose and a subsequent Mitsunobu inversion provided selectively the β-linked L-rhodinose-L-rhamnose disaccharide. Comparison with the reported data for the natural product and the aglycone suggests a misassignment of the structure of the natural product. Natural product reassignment: Total synthesis of the proposed structures for fulicineroside and its aglycone fulicinerine has been achieved (see figure). Key issues were the tetrasubstituted dibenzofuran and the trisaccharide with its β-linkage between L-rhodinose and L-rhamnose. A comparison with the reported data for the natural product and the aglycone suggests a misassignment of the structure of the natural product. Copyright

SYNTHESIS OF (L)-DAUNOSAMINE AND RELATED AMINO SUGARS

1-(2-Furyl)ethanol (6) has been converted into methyl (+/-)-daunosaminide (1) and methyl (+/-)-ristosaminide (3) by use of an intramolecular cyclisation of a trichloroacetimidate group. (+/-)-Daunosamine (1) has been obtained more directly from the alcohol (10) by use of a modified Mitsunobu reaction; the scope of the latter reaction has been explored using cyclohex-2-en-1-ol as a model substrate.Asymmetric reduction of 2-acetylfuran (5) has given (S)-1-(2-furyl)ethanol (46) in good enantiomeric excess, thus providing a short route to the L-enantiomers of the amino sugars (1), (2), and (3) from a cheap, non-carbohydrate precursor.

AN APPLICATION OF THE PALLADIUM-CATALYZED, ALLYLIC AMINATION OF UNSATURATED SUGARS: A NEW SYNTHESIS OF D-FOROSAMINE

Methyl 4-O-benzoyl-6-bromo-6-deoxy-α-D-glucopyranoside, obtainable from methyl 4,6-O-benzylidene-α-D-glucopyranoside (1), was converted into the 2,3-unsaturated 4-benzoate (3) by application of the triiodoimidazole method.Debenzoylation of 3, followed by