(2S,3R)-(para-bromophenyl)-2-benzylcarbamate-3-hydroxy-6-chlorohexanoate

Base Information

• Chemical Name: (2S,3R)-(para-bromophenyl)-2-benzylcarbamate-3-hydroxy-6-chlorohexanoate
• CAS No.: 298199-44-7
• Molecular Formula: C₂₀H₂₁BrClNO₅
• Molecular Weight: 470.747
• Mol file: 298199-44-7.mol

Synonyms:(2S,3R)-(para-bromophenyl)-2-benzylcarbamate-3-hydroxy-6-chlorohexanoate

Chemical Property of (2S,3R)-(para-bromophenyl)-2-benzylcarbamate-3-hydroxy-6-chlorohexanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-(para-bromophenyl)-2-benzylcarbamate-3-hydroxy-6-chlorohexanoate

There total 3 articles about (2S,3R)-(para-bromophenyl)-2-benzylcarbamate-3-hydroxy-6-chlorohexanoate 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:

O-benzyl carbamate (621-84-1) + (para-bromophenyl)-6-chloro-2-(E)-hexenoate (254115-09-8) → C20H21BrNO5Cl + (2S,3R)-(para-bromophenyl)-2-benzylcarbamate-3-hydroxy-6-chlorohexenoate (254115-13-4) + (2S,3R)-(para-bromophenyl)-2-benzylcarbamate-3-hydroxy-6-chlorohexanoate (298199-44-7)

Guidance literature:

With sodium hydroxide; tert-butylhypochlorite; potassium osmate(VI); In propan-1-ol; water; at 20 ℃; for 4h; Title compound not separated from byproducts.;

DOI:10.1021/ol9903032

Reference yield:

4-bromo-phenol (106-41-2) → (2S,3R)-(para-bromophenyl)-2-benzylcarbamate-3-hydroxy-6-chlorohexanoate (298199-44-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 100 percent / DCC / DMAP / CH₂Cl₂ / 10 h / 0 - 20 °C

2.1: NaH / tetrahydrofuran / 0.33 h / 0 - 20 °C

2.2: 90 percent / tetrahydrofuran / 1 h / 20 °C

3.1: sodium hydroxide; potassium osmate dihydrate; t-butyl hypochlorite / propan-1-ol / 0.08 h

3.2: (DHQD)2-AQN; potassium osmate dihydrate / propan-1-ol / 4 h / 20 °C

With sodium hydroxide; potassium osmate(VI); tert-butylhypochlorite; sodium hydride; dicyclohexyl-carbodiimide; dmap; In tetrahydrofuran; propan-1-ol; dichloromethane; 1.1: Addition / 2.1: Metallation / 2.2: Addition / 3.1: aminohydroxylation / 3.2: Addition;

DOI:10.1021/ol0061034

Reference yield:

(para-bromophenyl)diethylphosphonoacetate (254114-95-9) → (2S,3R)-(para-bromophenyl)-2-benzylcarbamate-3-hydroxy-6-chlorohexanoate (298199-44-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaH / tetrahydrofuran / 0.33 h / 0 - 20 °C

1.2: 90 percent / tetrahydrofuran / 1 h / 20 °C

2.1: sodium hydroxide; potassium osmate dihydrate; t-butyl hypochlorite / propan-1-ol / 0.08 h

2.2: (DHQD)2-AQN; potassium osmate dihydrate / propan-1-ol / 4 h / 20 °C

With sodium hydroxide; potassium osmate(VI); tert-butylhypochlorite; sodium hydride; In tetrahydrofuran; propan-1-ol; 1.1: Metallation / 1.2: Addition / 2.1: aminohydroxylation / 2.2: Addition;

DOI:10.1021/ol0061034

upstream raw materials:

O-benzyl carbamate

(para-bromophenyl)-6-chloro-2-(E)-hexenoate

4-bromo-phenol

(para-bromophenyl)diethylphosphonoacetate

Downstream raw materials:

(2S,3R)-6-Azido-2-benzyloxycarbonylamino-3-hydroxy-hexanoic acid 4-bromo-phenyl ester