116836-60-3

Upstream product

• 83803-07-0 methyl 2,3,6-trideoxy-3-trichloroacetamido-α-DL-ribohexopyranoside 
• 83803-06-9 2,3,4,6-tetradeoxy-4',5'-dihydro-2'-trichloromethyl(methyl α-DL-lyxo-hexopyranosido)<3,4-d>oxazole 
• 67-56-1 methanol 
• 142545-31-1 [(S)-3-Oxo-1-((4S,5S)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-propyl]-carbamic acid tert-butyl ester 
• 142545-24-2 4(S)-(N-Benzyl-N-tert-butoxycarbonyl)amino-6-benzyloxy-3(R)-hydroxyhexene-1 
• 142545-23-1 4(S)-(N-Benzyl-N-tert-butoxycarbonyl)amino-6-benzyloxy-1,2-2(S)-epoxy-3(S)-hydroxyhexane 
• 142545-29-7 4(S)-(N-Benzyl-N-tert-butyloxycarbonyl)amino-6-benzyloxy-2,3-(2S,3S)-isopropylidenedioxyhexane 
• 142545-32-2 Benzyl-[(1S,2S,3S)-1-(2-benzyloxy-ethyl)-2,3-dihydroxy-butyl]-carbamic acid tert-butyl ester 
• 142545-30-0 4(S)-(N-tert-Butyloxycarbonyl)amino-6-hydroxy-2,3-(2S,3S)-isopropylidenedioxyhexane 
• 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-threo-hex-2-enopyranoside 
• 4208-64-4 1-(2-furyl)ethanol 
• 26922-36-1 methyl 2,3,6-trideoxy-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 

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 
• 116724-61-9 C₁₀H₁₈ClN₃O₅ 

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.