(2S,3R)-2-benzyl-3-(benzyloxycarbonylamino)-4-hydroxybutanoic acid methyl ester

Base Information

Chemical Name:(2S,3R)-2-benzyl-3-(benzyloxycarbonylamino)-4-hydroxybutanoic acid methyl ester
CAS No.:349148-39-6
Molecular Formula:C₂₀H₂₃NO₅
Molecular Weight:357.406
Hs Code.:

Synonyms:(2S,3R)-2-benzyl-3-(benzyloxycarbonylamino)-4-hydroxybutanoic acid methyl ester

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Chemical Property of (2S,3R)-2-benzyl-3-(benzyloxycarbonylamino)-4-hydroxybutanoic acid methyl ester

Chemical Property:

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Technology Process of (2S,3R)-2-benzyl-3-(benzyloxycarbonylamino)-4-hydroxybutanoic acid methyl ester

There total 6 articles about (2S,3R)-2-benzyl-3-(benzyloxycarbonylamino)-4-hydroxybutanoic acid methyl ester 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:

: (2R,3S)-2-Benzyl-3-benzyloxycarbonylamino-succinic acid 4-(2,5-dioxo-pyrrolidin-1-yl) ester 1-methyl ester

: 349148-39-6
(2S,3R)-2-benzyl-3-(benzyloxycarbonylamino)-4-hydroxybutanoic acid methyl ester

Guidance literature:: With sodium tetrahydroborate; In tetrahydrofuran; at 0 - 20 ℃; for 18h;
DOI:10.1021/jo0014055

Reference yield:

: 100-39-0
benzyl bromide

: 349148-39-6
(2S,3R)-2-benzyl-3-(benzyloxycarbonylamino)-4-hydroxybutanoic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C

1.2: 61 percent / tetrahydrofuran; hexane / 6 h

2.1: acetyl chloride / methanol / 3 h / 0 °C

2.2: CuCO₃*Cu(OH)2 / H₂O / 3 h / 70 °C

3.1: Na₂CO₃ / H₂O / 4 h / 20 °C

4.1: DCC / 1,2-dimethoxy-ethane

5.1: NaBH₄ / tetrahydrofuran / 18 h / 0 - 20 °C

With sodium tetrahydroborate; sodium carbonate; acetyl chloride; dicyclohexyl-carbodiimide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; hexane; water;
DOI:10.1021/jo0014055

Reference yield:

: 130622-08-1
(2R)-2-tert-butoxycarbonylamino-succinic acid dimethyl ester

: 349148-39-6
(2S,3R)-2-benzyl-3-(benzyloxycarbonylamino)-4-hydroxybutanoic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C

1.2: 61 percent / tetrahydrofuran; hexane / 6 h

2.1: acetyl chloride / methanol / 3 h / 0 °C

2.2: CuCO₃*Cu(OH)2 / H₂O / 3 h / 70 °C

3.1: Na₂CO₃ / H₂O / 4 h / 20 °C

4.1: DCC / 1,2-dimethoxy-ethane

5.1: NaBH₄ / tetrahydrofuran / 18 h / 0 - 20 °C

With sodium tetrahydroborate; sodium carbonate; acetyl chloride; dicyclohexyl-carbodiimide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; hexane; water;
DOI:10.1021/jo0014055