(2S,3R)-N-(2,4-dimethoxybenzyl)-N-(t-butoxycarbonylmethyl)-2,3-epoxybutyramide

Base Information

• Chemical Name: (2S,3R)-N-(2,4-dimethoxybenzyl)-N-(t-butoxycarbonylmethyl)-2,3-epoxybutyramide
• CAS No.: 81902-68-3
• Molecular Formula: C₁₉H₂₇NO₆
• Molecular Weight: 365.426

Synonyms:(2S,3R)-N-(2,4-dimethoxybenzyl)-N-(t-butoxycarbonylmethyl)-2,3-epoxybutyramide

Chemical Property of (2S,3R)-N-(2,4-dimethoxybenzyl)-N-(t-butoxycarbonylmethyl)-2,3-epoxybutyramide

Chemical Property:

Purity/Quality:

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Technology Process of (2S,3R)-N-(2,4-dimethoxybenzyl)-N-(t-butoxycarbonylmethyl)-2,3-epoxybutyramide

There total 6 articles about (2S,3R)-N-(2,4-dimethoxybenzyl)-N-(t-butoxycarbonylmethyl)-2,3-epoxybutyramide 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: 85.0%

(2S,3R)-N-(2,4-dimethoxybenzyl)-N-(t-butoxycarbonylmethyl)-2-bromo-3-hydroxybutyramide (81902-59-2) → (2S,3R)-N-(2,4-dimethoxybenzyl)-N-(t-butoxycarbonylmethyl)-2,3-epoxybutyramide (81902-68-3)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; for 4h; Ambient temperature;

DOI:10.1016/S0040-4020(01)91132-9

Reference yield:

(2S,3R)-N-(2,4-dimethoxybenzyl)-N-(t-butoxycarbonylmethyl)-2-bromo-3-hydroxybutyramide (81902-59-2) → [(2,4-Dimethoxy-benzyl)-((2R,3R)-3-methyl-oxiranecarbonyl)-amino]-acetic acid tert-butyl ester (81902-68-3)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at 0 ℃; for 0.25h;

DOI:10.1016/S0040-4039(01)92460-8

Reference yield:

bromoacetic acid tert-butyl ester (5292-43-3) → (2S,3R)-N-(2,4-dimethoxybenzyl)-N-(t-butoxycarbonylmethyl)-2,3-epoxybutyramide (81902-68-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 58 percent / Et₃N / tetrahydrofuran / 1 h / Heating

2: 84 percent / N,N-dicyclohexylcarbodiimide / tetrahydrofuran / 0.25 h / 20 - 25 °C

3: 85 percent / DBU / tetrahydrofuran / 4 h / Ambient temperature

With 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran;

DOI:10.1016/S0040-4020(01)91132-9

upstream raw materials:

(2S,3R)-N-(2,4-dimethoxybenzyl)-N-(t-butoxycarbonylmethyl)-2-bromo-3-hydroxybutyramide

(2,4-dimethoxy-benzylamino)-acetic acid

bromoacetic acid tert-butyl ester

2,4-dimethoxybenzylamine hydrochloride

Downstream raw materials:

<3S-<3α(S^*),4β>>-t-butyl 1-(2,4-dimethoxybenzyl)-3-(1-hydroxyethyl)-2-azetidinone-4-carboxylate

<3S-<3α(S^*),4α>>-t-butyl 1-(2,4-dimethoxybenzyl)-3-(1-hydroxyethyl)-2-azetidinone-4-carboxylate

<3S-<3α(S^*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-4-methanesulfonyloxymethyl-2-azetidinone

<3S-<3α(S^*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-4-(2-oxo-3-chloropropyl)-2-azetidinone

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