100102-48-5

Basic information

• Product Name: Methyl-4-O-benzoyl-3,4,6-tridesoxy-β-D-erythro-hex-2-enopyranosid
• Synonyms: Methyl-4-O-benzoyl-3,4,6-tridesoxy-β-D-erythro-hex-2-enopyranosid
• CAS NO: 100102-48-5
• Molecular Weight: 248.279
• Mol File: 100102-48-5.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Methyl-4-O-benzoyl-3,4,6-tridesoxy-β-D-erythro-hex-2-enopyranosid(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl-4-O-benzoyl-3,4,6-tridesoxy-β-D-erythro-hex-2-enopyranosid(100102-48-5)
• EPA Substance Registry System: Methyl-4-O-benzoyl-3,4,6-tridesoxy-β-D-erythro-hex-2-enopyranosid(100102-48-5)

Safety Data

• Hazardous Substances Data: 100102-48-5(Hazardous Substances Data)

Upstream product

• 100164-72-5 Methyl-3,4,6-tridesoxy-α-D-erythro-hex-3-enopyranosid 
• 61135-30-6 Methyl-3,4,6-tridesoxy-β-D-glycero-hex-3-enopyranosid-2-ulose 
• 139656-47-6 methyl 2,6-dideoxy-3,4-bis-O-<(trifluoromethyl)sulfonyl>-β-D-arabino-hexopyranoside 
• 133814-52-5 methyl 2,6-dideoxy-β-D-xylo-hexopyranoside 
• 17676-16-3 Methyl 2,6-dideoxy-β-D-arabino-hexopyranoside 
• 63902-64-7 Methyl-3,4,6-tridesoxy-β-D-erythro-hex-3-enopyranosid 
• 65-85-0 benzoic acid 
• 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 

Downstream Products

• 100102-49-6 Methyl-4-O-benzoyl-2,3,6-tridesoxy-β-D-erythro-hexopyranosid 

Relevant articles and documents

A short and efficient transformation of rhamnose into activated daunosamine, acosamine, ristosamine and epi-daunosamine derivatives, and synthesis of an anthracycline antibiotic acosaminyl-ε-iso-rhodomycinone

3-Amino-2,3,6-trideoxyhexopyranoses are essential constituents of most anthracycline antitumour antibiotics. For an investigation of structure-activity relationships, the four diastereomeric amino sugars daunosamine, acosamine, ristosamine, and epidaunosamine were synthesised in short and efficient routes starting from commercially available rhamnose. Several glycosyl donors were provided and their use was exemplified in the synthesis of acosaminyl-ε-iso-rhodomycinone.

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.