tert-butyl (1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-4-(4-methylphenyl)-3-butenylcarbamate

Base Information

Chemical Name:tert-butyl (1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-4-(4-methylphenyl)-3-butenylcarbamate
CAS No.:308795-92-8
Molecular Formula:C₁₇H₂₅NO₄
Molecular Weight:307.39
Hs Code.:

Synonyms:tert-butyl (1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-4-(4-methylphenyl)-3-butenylcarbamate

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Chemical Property of tert-butyl (1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-4-(4-methylphenyl)-3-butenylcarbamate

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Technology Process of tert-butyl (1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-4-(4-methylphenyl)-3-butenylcarbamate

There total 4 articles about tert-butyl (1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-4-(4-methylphenyl)-3-butenylcarbamate 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: 79.0%

: 308795-89-3
tert-butyl (1S,2R)-2-hydroxy-1-(hydroxymethyl)-4-(4-methylphenyl)-3-butynylcarbamate

: 308795-92-8
tert-butyl (1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-4-(4-methylphenyl)-3-butenylcarbamate

Guidance literature:: With sodium bis(2-methoxyethoxy)aluminium dihydride; In diethyl ether; toluene; at 20 ℃;
DOI:10.1021/jm000939v

Reference yield:

: 102308-32-7
(4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

: 308795-92-8
tert-butyl (1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-4-(4-methylphenyl)-3-butenylcarbamate

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 2 h / -20 °C

1.2: 70 percent / HMPA / tetrahydrofuran; hexane / 3 h / -78 °C

2.1: 64 percent / p-TsOH; MeOH / 20 °C

3.1: 79 percent / red-Al / diethyl ether; toluene / 20 °C

With methanol; n-butyllithium; toluene-4-sulfonic acid; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; diethyl ether; hexane; toluene;
DOI:10.1021/jm000939v

Reference yield:

: 308795-88-2
tert-butyl (4S)-4-[(1R)-1-hydroxy-3-(4-methylphenyl)-2-propynyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

: 308795-92-8
tert-butyl (1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-4-(4-methylphenyl)-3-butenylcarbamate

Guidance literature:: Multi-step reaction with 2 steps

1: 64 percent / p-TsOH; MeOH / 20 °C

2: 79 percent / red-Al / diethyl ether; toluene / 20 °C

With methanol; toluene-4-sulfonic acid; sodium bis(2-methoxyethoxy)aluminium dihydride; In diethyl ether; toluene;
DOI:10.1021/jm000939v