61819-51-0

Basic information

• Product Name: methyl-4-O-benzoyl-2,3,6-tridesoxy-α-D-threo-hex-2-enopyranoside
• Synonyms: methyl-4-O-benzoyl-2,3,6-tridesoxy-α-D-threo-hex-2-enopyranoside
• CAS NO: 61819-51-0
• Molecular Weight: 248.279
• Mol File: 61819-51-0.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: methyl-4-O-benzoyl-2,3,6-tridesoxy-α-D-threo-hex-2-enopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl-4-O-benzoyl-2,3,6-tridesoxy-α-D-threo-hex-2-enopyranoside(61819-51-0)
• EPA Substance Registry System: methyl-4-O-benzoyl-2,3,6-tridesoxy-α-D-threo-hex-2-enopyranoside(61819-51-0)

Safety Data

• Hazardous Substances Data: 61819-51-0(Hazardous Substances Data)

Upstream product

• 65-85-0 benzoic acid 
• 321905-69-5 (2S,3R)-6-Methoxy-2-methyl-3,6-dihydro-2H-pyran-3-ol 
• 1192-62-7 1-(2-furyl)-1-ethanone 
• 33647-67-5 1-(2,5-dimethoxy-2,5-dihydrofuran-2-yl)ethanol from 2-Acetylfuran 
• 76739-66-7 3,4-di-O-acetyl-D-rhamnal 
• 33648-02-1 methyl-4-O-acetyl-2,3,6-tridesoxy-α-D-erythro-hex-2-enopyranoside 
• 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 
• 33647-98-2 methyl-2,3,6-tridesoxy-α-D-erythro-hex-2-enopyranoside 
• 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 
• 4208-64-4 1-(2-furyl)ethanol 
• 532-32-1 sodium benzoate 

Downstream Products

• 76793-59-4 4-Nitro-benzoic acid (2R,3R,4S,6S)-6-((1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy)-2-methyl-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-3-yl ester 
• 72384-25-9 1,5-anhydro-2,3,6-tridesoxy-4-O-p-nitrobenzoyl-3-trifluoroacetamido-D-xylo-hex-1-enitol 

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.

HEMISYNTHESE DE NOUVEAUX GLICOSIDES ANALOGUES DE LA DAUNORUBICINE

Seven daunorubicin analogs containing α-L-, α-D-, and β-D-glicosidic linkages, in which the natural occuring sugar (L-daunosamine) was replaced by diastereomeric 3-amino-2,3,6-trideoxyhexoses (3-epi-L-daunosamine, D-acosamine, D-daunosamine, D-ristosamine, and 3-epi-D-daunosamine), were prepared.In all cases, glycosidation with daunomycinone was performed in the presence of p-toluenesulfonic acid starting from 1-O-acetyl-2,3,6-trideoxy-4-O-p-nitrobenzoyl-3-trifluoro-acetamidohexopyranoses (prepared from the corresponding methyl 3-amino-2,3,6-trideoxyhexopyranosides) or from 1,5-anhydro-2,3,6-trideoxy-4-O-p-nitrobenzoyl-3-trifluoroacetamidohex-1-enitols (prepared from glycosals or pseudoglycals, the 3-amino group being introduced by substitution with sodium azide and subsequent reduction).Glycosidation was followed by removal of the protecting groups.