(2S,4S)-1-Tert-Butyl 2-Methyl 4-((Tert-Butyldimethylsilyl)Oxy)-5-Oxopyrrolidine-1,2-Dicarboxylate

Base Information

• Chemical Name: (2S,4S)-1-Tert-Butyl 2-Methyl 4-((Tert-Butyldimethylsilyl)Oxy)-5-Oxopyrrolidine-1,2-Dicarboxylate
• CAS No.: 367966-67-4
• Molecular Formula: C₁₇H₃₁NO₆Si
• Molecular Weight: 373.522
• Mol file: 367966-67-4.mol

Synonyms:(3S,5S)-1-tert-butoxycarbonyl-3-tert-butyldimethylsilyloxy-5-methoxycarbonylpyrrolidin-2-one;(2S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester;(3S,5S)-1-tert-butoxycarbonyl-3-(tert-butyldimethylsilyl)oxy-5-methoxycarbonylpyrrolidin-2-one;

Chemical Property of (2S,4S)-1-Tert-Butyl 2-Methyl 4-((Tert-Butyldimethylsilyl)Oxy)-5-Oxopyrrolidine-1,2-Dicarboxylate

Chemical Property:

• PSA: 82.14000
• LogP: 3.02370

Purity/Quality:

99% ^*data from raw suppliers

(2S,4S)-1-tert-Butyl2-methyl4-((tert-butyldimethylsilyl)oxy)-5-oxopyrrolidine-1,2-dicarboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4S)-1-Tert-Butyl 2-Methyl 4-((Tert-Butyldimethylsilyl)Oxy)-5-Oxopyrrolidine-1,2-Dicarboxylate

There total 6 articles about (2S,4S)-1-Tert-Butyl 2-Methyl 4-((Tert-Butyldimethylsilyl)Oxy)-5-Oxopyrrolidine-1,2-Dicarboxylate 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: 98.0%

(2S,4S)-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1,2-pyrrolidinedicarboxylic acid 1-(1,1-dimethylethyl) 2-methyl ester (367966-45-8) → 1-(tert-butyl) 2-methyl (2S,4S)-4-((tert-butyldimethylsilyl)oxy)-5-oxopyrrolidine-1,2-dicarboxylate (367966-67-4)

Guidance literature:

With sodium periodate; ruthenium (IV) oxide monohydrate; In water; ethyl acetate; at 20 ℃; for 6h;

DOI:10.1021/acsmedchemlett.0c00496

Reference yield:

(2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester (74844-91-0,114676-69-6,135042-17-0,227935-38-8,102195-79-9) → 1-(tert-butyl) 2-methyl (2S,4S)-4-((tert-butyldimethylsilyl)oxy)-5-oxopyrrolidine-1,2-dicarboxylate (367966-67-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C

2: sodium periodate; ruthenium(IV) oxide / water; ethyl acetate / 3 h / 20 °C

With 1H-imidazole; ruthenium(IV) oxide; sodium periodate; In water; ethyl acetate; N,N-dimethyl-formamide;

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 1-(tert-butyl) 2-methyl (2S,4S)-4-((tert-butyldimethylsilyl)oxy)-5-oxopyrrolidine-1,2-dicarboxylate (367966-67-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C

2: sodium periodate; ruthenium(IV) oxide / water; ethyl acetate / 3 h / 20 °C

With 1H-imidazole; ruthenium(IV) oxide; sodium periodate; In water; ethyl acetate; N,N-dimethyl-formamide;

upstream raw materials:

(2S,4S)-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1,2-pyrrolidinedicarboxylic acid 1-(1,1-dimethylethyl) 2-methyl ester

tert-butyldimethylsilyl chloride

(2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester

(2S,4S)-4-hydroxypyrrolidine-2-carboxylic acid hydrochloride

Downstream raw materials:

methyl (4S)-cis-N-Boc-4-hydroxyl pyroglutamate

febrifugine

(2R,3S)-3-benzyloxy-2-[2-oxo-3-(4-oxoquinazolin-3(4H)-yl)propyl]piperidine-1-carboxylic acid benzyl ester

(2R,3S)-3-Hydroxy-2-(2-methyl-allyl)-piperidine-1-carboxylic acid benzyl ester