(4R,5S,Z)-4-(benzyloxy)-5-((tert-butoxycarbonyl)amino)-6-hydroxyhex-2-en-1-yl acetate

Base Information

Chemical Name:(4R,5S,Z)-4-(benzyloxy)-5-((tert-butoxycarbonyl)amino)-6-hydroxyhex-2-en-1-yl acetate
CAS No.:1011247-68-9
Molecular Formula:C₂₀H₂₉NO₆
Molecular Weight:379.453
Hs Code.:

Synonyms:(4R,5S,Z)-4-(benzyloxy)-5-((tert-butoxycarbonyl)amino)-6-hydroxyhex-2-en-1-yl acetate

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Chemical Property of (4R,5S,Z)-4-(benzyloxy)-5-((tert-butoxycarbonyl)amino)-6-hydroxyhex-2-en-1-yl acetate

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Technology Process of (4R,5S,Z)-4-(benzyloxy)-5-((tert-butoxycarbonyl)amino)-6-hydroxyhex-2-en-1-yl acetate

There total 3 articles about (4R,5S,Z)-4-(benzyloxy)-5-((tert-butoxycarbonyl)amino)-6-hydroxyhex-2-en-1-yl acetate 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: 94.0%

: 1011247-66-7
(S)-tert-butyl 4-((R,Z)-4-acetoxy-1-(benzyloxy)but-2-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate

: 1011247-68-9
(4R,5S,Z)-4-(benzyloxy)-5-((tert-butoxycarbonyl)amino)-6-hydroxyhex-2-en-1-yl acetate

Guidance literature:: With Fe₃Cl-SiO₂; In chloroform; at 20 ℃;
DOI:10.1016/j.tetlet.2007.12.014

Reference yield:

: 1011247-64-5
(S)-tert-butyl 4-((R,Z)-1-(benzyloxy)-4-hydroxybut-2-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate

: 1011247-68-9
(4R,5S,Z)-4-(benzyloxy)-5-((tert-butoxycarbonyl)amino)-6-hydroxyhex-2-en-1-yl acetate

Guidance literature:: Multi-step reaction with 2 steps

1: dmap; triethylamine / dichloromethane / 0.17 h / 20 °C / Inert atmosphere

2: iron(III) chloride adsorbed on silica gel / chloroform / 12 h / Inert atmosphere

With dmap; iron(III) chloride adsorbed on silica gel; triethylamine; In dichloromethane; chloroform;
DOI:10.1039/c0ob00643b

Reference yield:

: 1011247-62-3
(S)-tert-butyl 4-((R,Z)-1-(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)but-2-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate

: 1011247-68-9
(4R,5S,Z)-4-(benzyloxy)-5-((tert-butoxycarbonyl)amino)-6-hydroxyhex-2-en-1-yl acetate

Guidance literature:: Multi-step reaction with 3 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.25 h / 20 °C / Inert atmosphere

2: dmap; triethylamine / dichloromethane / 0.17 h / 20 °C / Inert atmosphere

3: iron(III) chloride adsorbed on silica gel / chloroform / 12 h / Inert atmosphere

With dmap; iron(III) chloride adsorbed on silica gel; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; dichloromethane; chloroform;
DOI:10.1039/c0ob00643b