(2S,3R)-3-<(tert-butyldimethylsilyl)oxy>-N-(2,4-dimethoxybenzyl)-2-(phenylsulfinylmethyl)butanamide

Base Information

• Chemical Name: (2S,3R)-3-<(tert-butyldimethylsilyl)oxy>-N-(2,4-dimethoxybenzyl)-2-(phenylsulfinylmethyl)butanamide
• CAS No.: 137528-07-5
• Molecular Formula: C₂₆H₃₉NO₅SSi
• Molecular Weight: 505.751

Synonyms:(2S,3R)-3-<(tert-butyldimethylsilyl)oxy>-N-(2,4-dimethoxybenzyl)-2-(phenylsulfinylmethyl)butanamide

Chemical Property of (2S,3R)-3-<(tert-butyldimethylsilyl)oxy>-N-(2,4-dimethoxybenzyl)-2-(phenylsulfinylmethyl)butanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (2S,3R)-3-<(tert-butyldimethylsilyl)oxy>-N-(2,4-dimethoxybenzyl)-2-(phenylsulfinylmethyl)butanamide

There total 3 articles about (2S,3R)-3-<(tert-butyldimethylsilyl)oxy>-N-(2,4-dimethoxybenzyl)-2-(phenylsulfinylmethyl)butanamide 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: 89.0%

(2S,3R)-3-<(tert-butyldimethylsilyl)oxy>-N-(2,4-dimethoxybenzyl)-2-(phenylthiomethyl)butanamide (137528-04-2) → (2S,3R)-3-<(tert-butyldimethylsilyl)oxy>-N-(2,4-dimethoxybenzyl)-2-(phenylsulfinylmethyl)butanamide (137528-07-5)

Guidance literature:

With sodium periodate; In methanol; at 20 ℃; for 24h;

DOI:10.1039/c39900000727

Reference yield:

ethyl (3R)-3-<(tert-butyldimethylsilyl)oxy>-2-(phenylthiomethyl)butanoate (130164-35-1,130164-36-2) → (2S,3R)-3-<(tert-butyldimethylsilyl)oxy>-N-(2,4-dimethoxybenzyl)-2-(phenylsulfinylmethyl)butanamide (137528-07-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) AlMe₃ / 1.) hexane, benzene, from 0 deg C to RT, 1 h, 2.) hexane, benzene, reflux, 3 d

2: 89 percent / NaIO₄ / methanol / Ambient temperature

With sodium periodate; trimethylaluminum; In methanol;

DOI:10.1248/cpb.40.12

Reference yield:

2,4-dimethoxybenzylamine hydrochloride (20781-21-9) → (2S,3R)-3-<(tert-butyldimethylsilyl)oxy>-N-(2,4-dimethoxybenzyl)-2-(phenylsulfinylmethyl)butanamide (137528-07-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) AlMe₃ / 1.) hexane, benzene, from 0 deg C to RT, 1 h, 2.) hexane, benzene, reflux, 3 d

2: 89 percent / NaIO₄ / methanol / Ambient temperature

With sodium periodate; trimethylaluminum; In methanol;

DOI:10.1248/cpb.40.12

upstream raw materials:

(2S,3R)-3-<(tert-butyldimethylsilyl)oxy>-N-(2,4-dimethoxybenzyl)-2-(phenylthiomethyl)butanamide

ethyl (3R)-3-<(tert-butyldimethylsilyl)oxy>-2-(phenylthiomethyl)butanoate

2,4-dimethoxybenzylamine hydrochloride

Downstream raw materials:

(3S)-3-<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-1-(2,4-dimethoxybenzyl)-4-(phenylthio)azetidin-2-one

(3S,4S)-3-<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-1-(2,4-dimethoxybenzyl)-4-(phenylthio)azetidin-2-one

(3S,4R)-3-<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-1-(2,4-dimethoxybenzyl)-4-(phenylthio)azetidin-2-one

<3S-<3α(S^*),4β>>-benzyl<3-(1-t-butyldimethylsilyloxyethyl)-2-azetidinone-4-yl>acetate

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