(E,2S,3R)-8-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)-3-hydroxy-1-phenyloct-4-ene

Base Information

Chemical Name:(E,2S,3R)-8-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)-3-hydroxy-1-phenyloct-4-ene
CAS No.:872033-09-5
Molecular Formula:C₂₇H₃₆N₂O₅
Molecular Weight:468.593
Hs Code.:

Synonyms:(E,2S,3R)-8-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)-3-hydroxy-1-phenyloct-4-ene

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Chemical Property of (E,2S,3R)-8-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)-3-hydroxy-1-phenyloct-4-ene

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Technology Process of (E,2S,3R)-8-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)-3-hydroxy-1-phenyloct-4-ene

There total 6 articles about (E,2S,3R)-8-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)-3-hydroxy-1-phenyloct-4-ene 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: 96.0%

: 872033-26-6
(E,2S)-8-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)-3-oxo-1-phenyloct-4-ene

: 872033-09-5
(E,2S,3R)-8-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)-3-hydroxy-1-phenyloct-4-ene

Guidance literature:: (E,2S)-8-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)-3-oxo-1-phenyloct-4-ene; With lithium tri-t-butoxyaluminum hydride; In ethanol; at -78 - -60 ℃; for 2h;

With water; citric acid; In ethanol; Product distribution / selectivity;

Reference yield: 85.0%

: 872033-08-4
benzyl (4E,6R,7S)-7-[(tert-butoxycarbonyl)amino]-6-[(tert-butyl-dimethyl-silanyl)oxy]-8-phenyl-oct-4-enylcarbamate

: 872033-09-5
(E,2S,3R)-8-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)-3-hydroxy-1-phenyloct-4-ene

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 16h; Product distribution / selectivity;

Reference yield:

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

: 872033-09-5
(E,2S,3R)-8-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)-3-hydroxy-1-phenyloct-4-ene

Guidance literature:: Multi-step reaction with 3 steps

1.1: diisobutylaluminium hydride

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

2.2: 48 h

3.1: lithium tri-t-butoxyaluminum hydride / ethanol / -78 - -60 °C / Inert atmosphere

With diisobutylaluminium hydride; potassium carbonate; lithium tri-t-butoxyaluminum hydride; In ethanol; acetonitrile; 2.1: Horner-Wadsworth-Emmons olefination / 2.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1021/jm3001136