23089-59-0

Upstream product

• 4208-64-4 1-(2-furyl)ethanol 
• 1192-62-7 1-(2-furyl)-1-ethanone 
• 33647-67-5 1-(2,5-dimethoxy-2,5-dihydrofuran-2-yl)ethanol from 2-Acetylfuran 
• 65827-44-3 (R)-1-((2R,3R,5R)-3-Amino-5-methoxy-tetrahydro-furan-2-yl)-ethanol 
• 101677-66-1 Acetic acid (S)-1-((2R,3R,5S)-3-chloro-5-methoxy-tetrahydro-furan-2-yl)-ethyl ester 
• 101677-68-3 Acetic acid (S)-1-((2S,3S,5S)-3-amino-5-methoxy-tetrahydro-furan-2-yl)-ethyl ester 
• 97327-52-1 methyl 3-benzamido-4-O-benzoyl-2-bromo-2,3,6-trideoxy-α-DL-galactopyranoside 
• 97327-50-9 methyl 4-O-(N-benzoylbenzimidoyl)-2,3,6-trideoxy-α-DL-threo-hex-2-enopyranoside 
• 62774-42-9 methyl 3-benzamido-4-O-benzoyl-2,3,6-trideoxy-α-DL-lyxo-hexopyranoside 
• 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 
• 17016-64-7 methyl 3-benzamido-2,3,6-trideoxy-α-DL-lyxo-hexopyranoside 

Relevant academic research and scientific papers

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.

ELECTROPHILIC ADDITIONS CONTROLLED BY REMOTE SUBSTITUENTS. TOTAL SYNTHESIS OF DAUNOSAMINE.

A new route to daunosamine based on the stereospecific electrophilic addition to 2-acetoxy-7-oxabicyclohept-5-ene-2-carbonitrile is presented.