(1S,2R,3R)-6-benzyloxycarbonylamino-1-((S)-N-tert-butoxycarbonylpyrrolidin-2-yl)-2,3-epoxyhexanol

Base Information

Chemical Name:(1S,2R,3R)-6-benzyloxycarbonylamino-1-((S)-N-tert-butoxycarbonylpyrrolidin-2-yl)-2,3-epoxyhexanol
CAS No.:1372138-70-9
Molecular Formula:C₂₃H₃₄N₂O₆
Molecular Weight:434.533
Hs Code.:

Synonyms:(1S,2R,3R)-6-benzyloxycarbonylamino-1-((S)-N-tert-butoxycarbonylpyrrolidin-2-yl)-2,3-epoxyhexanol

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Chemical Property of (1S,2R,3R)-6-benzyloxycarbonylamino-1-((S)-N-tert-butoxycarbonylpyrrolidin-2-yl)-2,3-epoxyhexanol

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Technology Process of (1S,2R,3R)-6-benzyloxycarbonylamino-1-((S)-N-tert-butoxycarbonylpyrrolidin-2-yl)-2,3-epoxyhexanol

There total 4 articles about (1S,2R,3R)-6-benzyloxycarbonylamino-1-((S)-N-tert-butoxycarbonylpyrrolidin-2-yl)-2,3-epoxyhexanol 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: 53.0%

: 1372138-69-6
(1R,E)-6-benzyloxycarbonylamino-1-((S)-N-tert-butoxycarbonylpyrrolidin-2-yl)hex-2-en-1-ol

: 1372138-70-9
(1S,2R,3R)-6-benzyloxycarbonylamino-1-((S)-N-tert-butoxycarbonylpyrrolidin-2-yl)-2,3-epoxyhexanol

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20 ℃; for 16h;
DOI:10.1021/jm3001136

Reference yield:

: 1372138-68-5
(E)-6-(benzyloxycarbonylamino)-1-((S)-N-tert-butoxycarbonylpyrrolidin-2-yl)hex-2-en-1-one

: 1372138-70-9
(1S,2R,3R)-6-benzyloxycarbonylamino-1-((S)-N-tert-butoxycarbonylpyrrolidin-2-yl)-2,3-epoxyhexanol

Guidance literature:: Multi-step reaction with 2 steps

1: diisobutylaluminium hydride / toluene / -78 °C

2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 16 h / 0 - 20 °C

With diisobutylaluminium hydride; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; toluene;
DOI:10.1021/jm3001136

Reference yield:

: 14468-80-5
N-benzyloxycarbonylpyrrolidin-2-one

: 1372138-70-9
(1S,2R,3R)-6-benzyloxycarbonylamino-1-((S)-N-tert-butoxycarbonylpyrrolidin-2-yl)-2,3-epoxyhexanol

Guidance literature:: Multi-step reaction with 4 steps

1.1: diisobutylaluminium hydride

2.1: potassium carbonate / acetonitrile / 0.25 h / 25 °C / Inert atmosphere

2.2: 48 h

3.1: diisobutylaluminium hydride / toluene / -78 °C

4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 16 h / 0 - 20 °C

With diisobutylaluminium hydride; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; toluene; acetonitrile; 2.1: Horner-Wadsworth-Emmons olefination / 2.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1021/jm3001136