(+)-(2S,3R,4S)-2-acetamido-N-(benzyloxycarbonyl)-5,6-didehydro-3,4-O-isopropylidene-5-(nitromethyl)-3,4-piperidinediol

Base Information

Chemical Name:(+)-(2S,3R,4S)-2-acetamido-N-(benzyloxycarbonyl)-5,6-didehydro-3,4-O-isopropylidene-5-(nitromethyl)-3,4-piperidinediol
CAS No.:117097-31-1
Molecular Formula:C₁₉H₂₃N₃O₇
Molecular Weight:405.408
Hs Code.:

Synonyms:(+)-(2S,3R,4S)-2-acetamido-N-(benzyloxycarbonyl)-5,6-didehydro-3,4-O-isopropylidene-5-(nitromethyl)-3,4-piperidinediol

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Chemical Property of (+)-(2S,3R,4S)-2-acetamido-N-(benzyloxycarbonyl)-5,6-didehydro-3,4-O-isopropylidene-5-(nitromethyl)-3,4-piperidinediol

Chemical Property:

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Technology Process of (+)-(2S,3R,4S)-2-acetamido-N-(benzyloxycarbonyl)-5,6-didehydro-3,4-O-isopropylidene-5-(nitromethyl)-3,4-piperidinediol

There total 14 articles about (+)-(2S,3R,4S)-2-acetamido-N-(benzyloxycarbonyl)-5,6-didehydro-3,4-O-isopropylidene-5-(nitromethyl)-3,4-piperidinediol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 117097-24-2
5-azido-5-deoxy-2,3-O-isopropylidene-L-ribono-1,4-lactone

: 117097-31-1
(+)-(2S,3R,4S)-2-acetamido-N-(benzyloxycarbonyl)-5,6-didehydro-3,4-O-isopropylidene-5-(nitromethyl)-3,4-piperidinediol

Guidance literature:: Multi-step reaction with 9 steps

1: 88 percent / H₂ / Raney Ni / methanol

2: 1.) imidazole, 2.) NaH / DMF

3: 70 percent / NaBH₄ / ethanol

4: 88 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂

5: Ph₃P, DEAD / dimethylformamide

7: 99 percent / RuO₄ / CH₂Cl₂; CCl₄

8: NaH / 1,2-dimethoxy-ethane

9: 1.) p-TSOH, AC₂O, 2.) K₂CO₃ / 2.) benzene

With 1H-imidazole; sodium tetrahydroborate; ruthenium tetroxide; oxalyl dichloride; hydrogen; acetic anhydride; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; diethylazodicarboxylate; nickel; In methanol; tetrachloromethane; 1,2-dimethoxyethane; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja00229a069

Reference yield:

: 41546-21-8
L-ribose

: 117097-31-1
(+)-(2S,3R,4S)-2-acetamido-N-(benzyloxycarbonyl)-5,6-didehydro-3,4-O-isopropylidene-5-(nitromethyl)-3,4-piperidinediol

Guidance literature:: Multi-step reaction with 10 steps

2: 88 percent / H₂ / Raney Ni / methanol

3: 1.) imidazole, 2.) NaH / DMF

4: 70 percent / NaBH₄ / ethanol

5: 88 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂

6: Ph₃P, DEAD / dimethylformamide

8: 99 percent / RuO₄ / CH₂Cl₂; CCl₄

9: NaH / 1,2-dimethoxy-ethane

10: 1.) p-TSOH, AC₂O, 2.) K₂CO₃ / 2.) benzene

With 1H-imidazole; sodium tetrahydroborate; ruthenium tetroxide; oxalyl dichloride; hydrogen; acetic anhydride; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; diethylazodicarboxylate; nickel; In methanol; tetrachloromethane; 1,2-dimethoxyethane; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja00229a069

Reference yield:

: 117179-01-8
5-amino-5-deoxy-2,3-O-isopropylidene-L-1,5-ribonolactam

: 117097-31-1
(+)-(2S,3R,4S)-2-acetamido-N-(benzyloxycarbonyl)-5,6-didehydro-3,4-O-isopropylidene-5-(nitromethyl)-3,4-piperidinediol

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) imidazole, 2.) NaH / DMF

2: 70 percent / NaBH₄ / ethanol

3: 88 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂

4: Ph₃P, DEAD / dimethylformamide

6: 99 percent / RuO₄ / CH₂Cl₂; CCl₄

7: NaH / 1,2-dimethoxy-ethane

8: 1.) p-TSOH, AC₂O, 2.) K₂CO₃ / 2.) benzene

With 1H-imidazole; sodium tetrahydroborate; ruthenium tetroxide; oxalyl dichloride; acetic anhydride; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrachloromethane; 1,2-dimethoxyethane; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja00229a069