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

Base Information

Chemical Name:(-)-(4S,5R,6S)-6-acetamido-N-(benzyloxycarbonyl)-2,3-didehydro-4,5-(isopropylidenedioxy)-3-piperidinecarboxylic acid methoxyethoxymethyl ester
CAS No.:125165-39-1
Molecular Formula:C₂₃H₃₀N₂O₉
Molecular Weight:478.499
Hs Code.:

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

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

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Chemical Property of (-)-(4S,5R,6S)-6-acetamido-N-(benzyloxycarbonyl)-2,3-didehydro-4,5-(isopropylidenedioxy)-3-piperidinecarboxylic acid methoxyethoxymethyl ester

Chemical Property:

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Technology Process of (-)-(4S,5R,6S)-6-acetamido-N-(benzyloxycarbonyl)-2,3-didehydro-4,5-(isopropylidenedioxy)-3-piperidinecarboxylic acid methoxyethoxymethyl ester

There total 18 articles about (-)-(4S,5R,6S)-6-acetamido-N-(benzyloxycarbonyl)-2,3-didehydro-4,5-(isopropylidenedioxy)-3-piperidinecarboxylic acid methoxyethoxymethyl ester 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

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

Guidance literature:: Multi-step reaction with 11 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

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 pyridine; methanol; tetrachloromethane; 1,2-dimethoxyethane; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja00229a069

Reference yield:

: 41546-21-8
L-ribose

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

Guidance literature:: Multi-step reaction with 12 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

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 pyridine; 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

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

Guidance literature:: Multi-step reaction with 10 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

9: 80 percent / pyridine / 38 °C

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

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