tert-butyl (1S,2R_.3E)-4-(4-fluorophenyl)-2-hydroxy-1-(hydroxymethyl)-3-butenylcarbamate

Base Information

• Chemical Name: tert-butyl (1S,2R_.3E)-4-(4-fluorophenyl)-2-hydroxy-1-(hydroxymethyl)-3-butenylcarbamate
• CAS No.: 308796-35-2
• Molecular Formula: C₁₆H₂₂FNO₄
• Molecular Weight: 311.353

Synonyms:tert-butyl (1S,2R_.3E)-4-(4-fluorophenyl)-2-hydroxy-1-(hydroxymethyl)-3-butenylcarbamate

Chemical Property of tert-butyl (1S,2R_.3E)-4-(4-fluorophenyl)-2-hydroxy-1-(hydroxymethyl)-3-butenylcarbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of tert-butyl (1S,2R_.3E)-4-(4-fluorophenyl)-2-hydroxy-1-(hydroxymethyl)-3-butenylcarbamate

There total 4 articles about tert-butyl (1S,2R_.3E)-4-(4-fluorophenyl)-2-hydroxy-1-(hydroxymethyl)-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: 72.0%

tert-butyl (1S,2R)-4-(4-fluorophenyl)-2-hydroxy-1-(hydroxymethyl)-3-butynylcarbamate (308796-33-0) → tert-butyl (1S,2R.3E)-4-(4-fluorophenyl)-2-hydroxy-1-(hydroxymethyl)-3-butenylcarbamate (308796-35-2)

Guidance literature:

With sodium bis(2-methoxyethoxy)aluminium dihydride; In diethyl ether; toluene; at 20 ℃;

DOI:10.1021/jm000939v

Reference yield:

1-ethynyl-4-fluorobenzene (766-98-3) → tert-butyl (1S,2R.3E)-4-(4-fluorophenyl)-2-hydroxy-1-(hydroxymethyl)-3-butenylcarbamate (308796-35-2)

Guidance literature:

Multi-step reaction with 3 steps

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

1.2: 89 percent / HMPA / tetrahydrofuran; hexane / 3 h / -78 °C

2.1: 72 percent / p-TsOH; MeOH / 20 °C

3.1: 72 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:

(4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (102308-32-7) → tert-butyl (1S,2R.3E)-4-(4-fluorophenyl)-2-hydroxy-1-(hydroxymethyl)-3-butenylcarbamate (308796-35-2)

Guidance literature:

Multi-step reaction with 3 steps

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

1.2: 89 percent / HMPA / tetrahydrofuran; hexane / 3 h / -78 °C

2.1: 72 percent / p-TsOH; MeOH / 20 °C

3.1: 72 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

upstream raw materials:

tert-butyl (1S,2R)-4-(4-fluorophenyl)-2-hydroxy-1-(hydroxymethyl)-3-butynylcarbamate

1-ethynyl-4-fluorobenzene

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

tert-butyl (4S)-4-[(1R)-3-(4-fluorophenyl)-1-hydroxy-2-propynyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

Downstream raw materials:

(E)-(2S,3R)-2-Amino-5-(4-fluoro-phenyl)-pent-4-ene-1,3-diol

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