131896-61-2

Upstream product

• 83803-07-0 methyl 2,3,6-trideoxy-3-trichloroacetamido-α-DL-ribohexopyranoside 
• 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 
• 33647-82-4 methyl 2,3,6-trideoxy-α-DL-glycero-hex-2-enopyranosid-4-ulose 
• 83803-03-6 methyl 2,3,6-trideoxy-4-O-trichloroacetimidoyl-α-DL-erythro-hex-2-enopyranoside 
• 83803-05-8 2,3,4,6-tetradeoxy-4',5'-dihydro-2-iodo-2'-trichloromethyl(methyl α-DL-altropyranosido)<3,4-d>oxazole 
• 89128-77-8 methyl 2,3,6-trideoxy-2-iodo-3-trichloroacetamido-α-DL-altropyranoside 
• 83803-03-6 methyl 2,3,6-trideoxy-4-O-trichloroacetimidoyl-α-DL-threo-hex-2-enopyranoside 
• 83803-05-8 2,3,4,6-tetradeoxy-4',5'-dihydro-2-iodo-2'-trichloromethyl(methyl α-DL-altropyranosido)<3,4-d>oxazole 
• 142545-30-0 4(S)-(N-tert-Butyloxycarbonyl)amino-6-hydroxy-2,3-(2S,3S)-isopropylidenedioxyhexane 
• 83803-06-9 2,3,4,6-tetradeoxy-4',5'-dihydro-2'-trichloromethyl(methyl α-DL-lyxo-hexopyranosido)<3,4-d>oxazole 
• 142545-29-7 4(S)-(N-Benzyl-N-tert-butyloxycarbonyl)amino-6-benzyloxy-2,3-(2S,3S)-isopropylidenedioxyhexane 
• 142545-23-1 4(S)-(N-Benzyl-N-tert-butoxycarbonyl)amino-6-benzyloxy-1,2-2(S)-epoxy-3(S)-hydroxyhexane 

Downstream Products

• 6605-26-1 N,O-diacetyl-α-daunosaminide 
• 6605-26-1 N,O-Diacetyl-L-daunosamine α-methylglycoside 
• 6605-26-1 N,O-Diacetyl-L-daunosamine β-methylglycoside 

Relevant academic research and scientific papers

The total synthesis of L-daunosamine

N,O-Dibenzyl-N-tert-butoxycarbonyl-L-homoserinal (7), obtained from L-aspartic acid, reacts with vinylmagnesium chloride to afford with high stereoselectivity compound 6 which is subsequently transformed into the derivative of L

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.