benzyl (4-bromo-2-(((2R,3S)-3-(hydroxymethyl)oxiran-2-yl)methoxy)phenyl)carbamate

Base Information

Chemical Name:benzyl (4-bromo-2-(((2R,3S)-3-(hydroxymethyl)oxiran-2-yl)methoxy)phenyl)carbamate
CAS No.:911845-41-5
Molecular Formula:C₁₈H₁₈BrNO₅
Molecular Weight:408.249
Hs Code.:

Synonyms:benzyl (4-bromo-2-(((2R,3S)-3-(hydroxymethyl)oxiran-2-yl)methoxy)phenyl)carbamate

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Chemical Property of benzyl (4-bromo-2-(((2R,3S)-3-(hydroxymethyl)oxiran-2-yl)methoxy)phenyl)carbamate

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Technology Process of benzyl (4-bromo-2-(((2R,3S)-3-(hydroxymethyl)oxiran-2-yl)methoxy)phenyl)carbamate

There total 13 articles about benzyl (4-bromo-2-(((2R,3S)-3-(hydroxymethyl)oxiran-2-yl)methoxy)phenyl)carbamate 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: 90.0%

: (2R,3R)-3-((2-(((benzyloxy)carbonyl)amino)-5-bromophenoxy)methyl)oxirane-2-carboxylic acid methyl ester

: 911845-41-5
benzyl (4-bromo-2-(((2R,3S)-3-(hydroxymethyl)oxiran-2-yl)methoxy)phenyl)carbamate

Guidance literature:: With sodium tetrahydroborate; ethanol; In tetrahydrofuran; at 0 ℃; for 2h;

Reference yield: 61.3%

: 911845-39-1
benzyl (Z)-(4-bromo-2-((4-hydroxybut-2-en-1-yl)oxy)phenyl)carbamate

: 911845-41-5
benzyl (4-bromo-2-(((2R,3S)-3-(hydroxymethyl)oxiran-2-yl)methoxy)phenyl)carbamate

Guidance literature:: benzyl (Z)-(4-bromo-2-((4-hydroxybut-2-en-1-yl)oxy)phenyl)carbamate; With diethyl (2R,3R)-tartrate; titanium(IV)isopropoxide; In dichloromethane; at -40 ℃; for 1h; Molecular sieve; Inert atmosphere;

With tert.-butylhydroperoxide; In dichloromethane; toluene; at -40 - -20 ℃; for 26h; Inert atmosphere; Molecular sieve;
DOI:10.1021/acsmedchemlett.7b00068

Reference yield:

: 321-23-3
4-bromo-2-fluoronitrobenzene

: 911845-41-5
benzyl (4-bromo-2-(((2R,3S)-3-(hydroxymethyl)oxiran-2-yl)methoxy)phenyl)carbamate

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 0 °C

1.2: 1 h / 20 °C

2.1: ammonium chloride; zinc / tetrahydrofuran / 20 °C

3.1: sodium hydrogencarbonate / tetrahydrofuran; water / 0 - 20 °C

4.1: tert.-butylhydroperoxide; titanium acetate; diethyl (2R,3R)-tartrate / dichloromethane; toluene / 20 h / -40 °C / Molecular sieve

With tert.-butylhydroperoxide; titanium acetate; diethyl (2R,3R)-tartrate; sodium hydride; sodium hydrogencarbonate; ammonium chloride; zinc; In tetrahydrofuran; dichloromethane; water; toluene; mineral oil; 4.1: Sharpless epoxidation;
DOI:10.1021/jm200614t