58769-79-2

Upstream product

• 67-56-1 methanol 
• 98-88-4 benzoyl chloride 
• 192824-05-8 (3S,4S,5R)-3-(N-tert-butoxycarbonylamino)-5-dihydroxy-4-hexanolactone 
• 192824-01-4 (2S,3S)-2-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-oxo-tetrahydro-furan-3-carboxylic acid 
• 192824-03-6 {(2S,3S)-2-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-oxo-tetrahydro-furan-3-yl}-carbamic acid tert-butyl ester 
• 192824-00-3 (R)-4-Benzhydryl-3-{(2S,3S)-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-oxo-tetrahydro-furan-3-carbonyl}-oxazolidin-2-one 
• 62774-42-9 methyl 3-benzamido-4-O-benzoyl-2,3,6-trideoxy-α-DL-lyxo-hexopyranoside 
• 97327-52-1 methyl 3-benzamido-4-O-benzoyl-2-bromo-2,3,6-trideoxy-α-DL-galactopyranoside 
• 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 
• 97327-50-9 methyl 4-O-(N-benzoylbenzimidoyl)-2,3,6-trideoxy-α-DL-threo-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 

Downstream Products

• 17016-65-8 N-((2R,3S,4S)-3,6-Dihydroxy-2-methyl-tetrahydro-pyran-4-yl)-benzamide 
• 18977-93-0 3-amino-2,3,6-trideoxy-DL-lyxo-hexopyranoside hydrochloride 

Relevant academic research and scientific papers

A new route to 3-amino sugars. A concise synthesis of L-daunosamine and D-ristosamine derivatives

An asymmetric aldol strategy has been developed for the synthesis of L- daunosamine and D-ristosamine derivatives starting from noncarbohydrate precursors. Lithium and boron enolate mediated aldol reactions of 12 with O- TBS lactaldehyde gave non-Evans syn and Evans syn aldol products, respectively, with high selectivity. The chemical efficiency of the lithium enolate reactions were higher than the corresponding reactions with the boron enolates. Curtius rearrangement of lactone acids 23 and 26 gave the corresponding N-BOC amino lactones 30 and 32 in 64% and 62%, respectively, with complete retention of configuration. Lactone 30 was converted by a two- step sequence to N-benzoyldaunosamide 40. The overall yield for the amino sugar 40 was 18% over six steps. Similary, lactone 32 was converted to N- benzoylristosamide 42 with an overall yield of 18% starting from 12.

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.

A New Route to (+/-)-Daunosamine and Related Amino-sugars

1-(2-Furyl)ethanol has been converted into (+/-)-daunosamine by use of a modified Mitsunobu reaction.