tert-butyl (2E)-3-[(4R,5R)-4-benzyl-N-(tert-butoxycarbonyl)-5-methyloxazolidin-2-on-5-yl]prop-2-enoate

Base Information

Chemical Name:tert-butyl (2E)-3-[(4R,5R)-4-benzyl-N-(tert-butoxycarbonyl)-5-methyloxazolidin-2-on-5-yl]prop-2-enoate
CAS No.:420803-59-4
Molecular Formula:C₂₃H₃₁NO₆
Molecular Weight:417.502
Hs Code.:

Synonyms:tert-butyl (2E)-3-[(4R,5R)-4-benzyl-N-(tert-butoxycarbonyl)-5-methyloxazolidin-2-on-5-yl]prop-2-enoate

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Chemical Property of tert-butyl (2E)-3-[(4R,5R)-4-benzyl-N-(tert-butoxycarbonyl)-5-methyloxazolidin-2-on-5-yl]prop-2-enoate

Chemical Property:

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Technology Process of tert-butyl (2E)-3-[(4R,5R)-4-benzyl-N-(tert-butoxycarbonyl)-5-methyloxazolidin-2-on-5-yl]prop-2-enoate

There total 14 articles about tert-butyl (2E)-3-[(4R,5R)-4-benzyl-N-(tert-butoxycarbonyl)-5-methyloxazolidin-2-on-5-yl]prop-2-enoate 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:

: 27784-76-5
tert-butyl diethylphosphonoacetate

: (4R,5S)-4-Benzyl-5-formyl-5-methyl-2-oxo-oxazolidine-3-carboxylic acid tert-butyl ester

: 420803-59-4
tert-butyl (2E)-3-[(4R,5R)-4-benzyl-N-(tert-butoxycarbonyl)-5-methyloxazolidin-2-on-5-yl]prop-2-enoate

Guidance literature:: tert-butyl diethylphosphonoacetate; With N-ethyl-N,N-diisopropylamine; lithium chloride; In acetonitrile; at 0 ℃;

(4R,5S)-4-Benzyl-5-formyl-5-methyl-2-oxo-oxazolidine-3-carboxylic acid tert-butyl ester; In acetonitrile; at 0 ℃;
DOI:10.1039/b203482d

Reference yield:

: 18942-49-9
Boc-D-Phe-OH

: 420803-59-4
tert-butyl (2E)-3-[(4R,5R)-4-benzyl-N-(tert-butoxycarbonyl)-5-methyloxazolidin-2-on-5-yl]prop-2-enoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 97 percent / DCC; (i-Pr)2NEt / dimethylformamide

2.1: tetrahydrofuran

2.2: CeCl₃ / tetrahydrofuran

3.1: 85 percent / NaH / tetrahydrofuran

4.1: O₃ / ethyl acetate

4.2: dimethyl sulfide / ethyl acetate

5.1: LiCl; N,N-diisopropylamine / acetonitrile / 1 h / 0 °C

5.2: acetonitrile / 2 h / 0 °C

With sodium hydride; ozone; diisopropylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; lithium chloride; In tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 5.1: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/ol016835b

Reference yield:

: 19901-50-9,51987-73-6,77119-84-7
methyl (2R)-2-(t-butoxycarbonylamino)-3-phenylpropionate

: 420803-59-4
tert-butyl (2E)-3-[(4R,5R)-4-benzyl-N-(tert-butoxycarbonyl)-5-methyloxazolidin-2-on-5-yl]prop-2-enoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: DIBAL-H / CH₂Cl₂; toluene

1.2: 52 percent / tetrahydrofuran

2.1: (COCl)2; DMSO; (i-Pr)2NEt / CH₂Cl₂

3.1: CeCl₃ / tetrahydrofuran

4.1: 85 percent / NaH / tetrahydrofuran

5.1: O₃ / ethyl acetate

5.2: dimethyl sulfide / ethyl acetate

6.1: LiCl; N,N-diisopropylamine / acetonitrile / 1 h / 0 °C

6.2: acetonitrile / 2 h / 0 °C

With cerium(III) chloride; oxalyl dichloride; sodium hydride; diisobutylaluminium hydride; ozone; dimethyl sulfoxide; diisopropylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene; acetonitrile; 2.1: Swern oxidation / 6.1: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/ol016835b