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

Base Information

Chemical Name:(+)-(2S,3R,4S,5R)-2-acetamido-N-(benzyloxycarbonyl)-5-(hydroxymethyl)-3,4-O-isopropylidene-3,4-piperidinediol
CAS No.:117097-34-4
Molecular Formula:C₁₉H₂₆N₂O₆
Molecular Weight:378.425
Hs Code.:

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

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

Chemical Property:

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

There total 18 articles about (+)-(2S,3R,4S,5R)-2-acetamido-N-(benzyloxycarbonyl)-5-(hydroxymethyl)-3,4-O-isopropylidene-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: 76.0%

: 125165-39-1
(-)-(4S,5R,6S)-6-acetamido-N-(benzyloxycarbonyl)-2,3-didehydro-4,5-(isopropylidenedioxy)-3-piperidinecarboxylic acid methoxyethoxymethyl ester

: 117097-34-4
(+)-(2S,3R,4S,5R)-2-acetamido-N-(benzyloxycarbonyl)-5-(hydroxymethyl)-3,4-O-isopropylidene-3,4-piperidinediol

Guidance literature:: With sodium tetrahydroborate; In tetrahydrofuran; for 3h; Ambient temperature;
DOI:10.1246/bcsj.65.978

Reference yield:

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

: 117097-34-4
(+)-(2S,3R,4S,5R)-2-acetamido-N-(benzyloxycarbonyl)-5-(hydroxymethyl)-3,4-O-isopropylidene-3,4-piperidinediol

Guidance literature:: Multi-step reaction with 12 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

10: 80 percent / pyridine / 38 °C

11: 1.) CH₃CH=C(CH₃)2, NaOCl₂-NaH₂PO₄, 2.) (i-Pr)2NEt / 1.) t-BuOH, H₂O; 2.) CH₂Cl₂

12: 75 percent / NaBH₄ / tetrahydrofuran; various solvent(s)

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

Reference yield:

: 41546-21-8
L-ribose

: 117097-34-4
(+)-(2S,3R,4S,5R)-2-acetamido-N-(benzyloxycarbonyl)-5-(hydroxymethyl)-3,4-O-isopropylidene-3,4-piperidinediol

Guidance literature:: Multi-step reaction with 13 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

11: 80 percent / pyridine / 38 °C

12: 1.) CH₃CH=C(CH₃)2, NaOCl₂-NaH₂PO₄, 2.) (i-Pr)2NEt / 1.) t-BuOH, H₂O; 2.) CH₂Cl₂

13: 75 percent / NaBH₄ / tetrahydrofuran; various solvent(s)

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