(2S,3R,4S,5S)-8-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)-4,5-epoxy-3-hydroxy-1-phenyloctane

Base Information

Chemical Name:(2S,3R,4S,5S)-8-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)-4,5-epoxy-3-hydroxy-1-phenyloctane
CAS No.:872033-18-6
Molecular Formula:C₂₇H₃₆N₂O₆
Molecular Weight:484.593
Hs Code.:

Synonyms:(2S,3R,4S,5S)-8-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)-4,5-epoxy-3-hydroxy-1-phenyloctane

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Chemical Property of (2S,3R,4S,5S)-8-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)-4,5-epoxy-3-hydroxy-1-phenyloctane

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Technology Process of (2S,3R,4S,5S)-8-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)-4,5-epoxy-3-hydroxy-1-phenyloctane

There total 6 articles about (2S,3R,4S,5S)-8-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)-4,5-epoxy-3-hydroxy-1-phenyloctane 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: 72.0%

: 872033-27-7
(E,2S,3S)-8-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)-3-hydroxy-1-phenyloct-4-ene

: 872033-18-6
(2S,3R,4S,5S)-8-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)-4,5-epoxy-3-hydroxy-1-phenyloctane

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

Reference yield:

: 69261-54-7,125982-42-5
1-(benzyloxycarbonyl)pyrrolidin-2-ol

: 872033-18-6
(2S,3R,4S,5S)-8-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)-4,5-epoxy-3-hydroxy-1-phenyloctane

Guidance literature:: Multi-step reaction with 3 steps

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

1.2: 48 h

2.1: L-Selectride / tetrahydrofuran; methanol / 3 h / -78 °C / Inert atmosphere

3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 16 h / 0 - 20 °C

With L-Selectride; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; 1.1: Horner-Wadsworth-Emmons olefination / 1.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1021/jm3001136

Reference yield:

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

: 872033-18-6
(2S,3R,4S,5S)-8-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)-4,5-epoxy-3-hydroxy-1-phenyloctane

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: L-Selectride / tetrahydrofuran; methanol / 3 h / -78 °C / Inert atmosphere

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

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