(2R,3S)-3-tert-Butoxycarbonylamino-4-phenyl-2-triisopropylsilanyloxy-butyric acid methyl ester

Base Information

• Chemical Name: (2R,3S)-3-tert-Butoxycarbonylamino-4-phenyl-2-triisopropylsilanyloxy-butyric acid methyl ester
• CAS No.: 203806-60-4
• Molecular Formula: C₂₅H₄₃NO₅Si
• Molecular Weight: 465.706
• Mol file: 203806-60-4.mol

Synonyms:(2R,3S)-3-tert-Butoxycarbonylamino-4-phenyl-2-triisopropylsilanyloxy-butyric acid methyl ester

Chemical Property of (2R,3S)-3-tert-Butoxycarbonylamino-4-phenyl-2-triisopropylsilanyloxy-butyric acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-3-tert-Butoxycarbonylamino-4-phenyl-2-triisopropylsilanyloxy-butyric acid methyl ester

There total 9 articles about (2R,3S)-3-tert-Butoxycarbonylamino-4-phenyl-2-triisopropylsilanyloxy-butyric 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: 95.0%

methanol (67-56-1) + (2S,3R)-2-Benzyl-4-oxo-3-triisopropylsilanyloxy-azetidine-1-carboxylic acid tert-butyl ester (203806-57-9) → (2R,3S)-3-tert-Butoxycarbonylamino-4-phenyl-2-triisopropylsilanyloxy-butyric acid methyl ester (203806-60-4)

Guidance literature:

With dmap; triethylamine; for 20h; Ambient temperature;

DOI:10.1016/S0040-4039(97)10677-3

Reference yield:

phenylmagnesium bromide (100-58-3) → (2R,3S)-3-tert-Butoxycarbonylamino-4-phenyl-2-triisopropylsilanyloxy-butyric acid methyl ester (203806-60-4)

Guidance literature:

Multi-step reaction with 5 steps

1: -70 - -40 °C

2: DMAP / Ambient temperature

3: 74 percent / H₂ / ethyl acetate / 40 °C / 5171.5 Torr

4: 1.) CAN

5: 95 percent / Et₃N, DMAP / 20 h / Ambient temperature

With dmap; ammonium cerium(IV) nitrate; hydrogen; triethylamine; In ethyl acetate;

DOI:10.1016/S0040-4039(97)10677-3

Reference yield:

(3R,4R)-1-(4-methoxyphenyl)-3-triisopropylsiloxy-4-formylazetidin-2-one (245657-85-6) → (2R,3S)-3-tert-Butoxycarbonylamino-4-phenyl-2-triisopropylsilanyloxy-butyric acid methyl ester (203806-60-4)

Guidance literature:

Multi-step reaction with 5 steps

1: -70 - -40 °C

2: DMAP / Ambient temperature

3: 74 percent / H₂ / ethyl acetate / 40 °C / 5171.5 Torr

4: 1.) CAN

5: 95 percent / Et₃N, DMAP / 20 h / Ambient temperature

With dmap; ammonium cerium(IV) nitrate; hydrogen; triethylamine; In ethyl acetate;

DOI:10.1016/S0040-4039(97)10677-3

upstream raw materials:

methanol

(2S,3R)-2-Benzyl-4-oxo-3-triisopropylsilanyloxy-azetidine-1-carboxylic acid tert-butyl ester

di-tert-butyl dicarbonate

phenylmagnesium bromide

Downstream raw materials:

(2R,3S)-N-(tert-butoxycarbonyl)-3-amino-2-hydroxy-4-phenylbutanoic acid methyl ester

((1S,2R)-1-benzyl-2,3-dihydroxypropyl)carbamic acid tert-butyl ester

(4S,5R)-4-Benzyl-5-((S)-1-hydroxy-but-3-enyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

(4S,5S)-4-Benzyl-5-but-3-enyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester