(2S,3S,4S)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-(1-formyl-2-phenylsulfanyl-ethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (2S,3S,4S)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-(1-formyl-2-phenylsulfanyl-ethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
• CAS No.: 103314-30-3
• Molecular Formula: C₃₃H₅₉NO₅SSi₂
• Molecular Weight: 638.072
• Mol file: 103314-30-3.mol

Synonyms:

Chemical Property of (2S,3S,4S)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-(1-formyl-2-phenylsulfanyl-ethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4S)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-(1-formyl-2-phenylsulfanyl-ethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

There total 9 articles about (2S,3S,4S)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-(1-formyl-2-phenylsulfanyl-ethyl)-pyrrolidine-1-carboxylic acid tert-butyl 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: 93.0%

(3S,4S,5S)-2-<1-(tert-butyloxycarbonyl)-4-<2-<(tert-butyldimethylsilyl)oxy>ethyl>-5-<<(tert-butyldimethylsilyl)oxy>methyl>-3-pyrrolidinyl>acrylaldehyde (103314-29-0) + thiophenol (108-98-5) → (2S,3S,4S)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-(1-formyl-2-phenylsulfanyl-ethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (103314-30-3,103314-37-0,111563-58-7)

Guidance literature:

With triethylamine; at 0 ℃; for 1h;

DOI:10.1016/S0040-4039(00)84053-8

Reference yield:

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile (58632-95-4) → (2S,3S,4S)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-(1-formyl-2-phenylsulfanyl-ethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (103314-30-3,103314-37-0,111563-58-7)

Guidance literature:

Multi-step reaction with 8 steps

1: triethylamine / H₂O; dioxane / 3 h / Ambient temperature

2: 100 percent / diethyl ether; methanol

3: 100 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / 0 °C

4: 70 percent / imidazole / dimethylformamide / 1.) 0 deg C, 30 min; 2.) r.t., 30 min

5: 97 percent / mCPBA / CH₂Cl₂ / Ambient temperature

6: lithium tetramethylpiperidine / diethyl ether / 1.) 0 deg C, 1 h; 2.) r.t., 1 h

7: 86 percent / MnO₂ / hexane / 1 h / Ambient temperature

8: 93 percent / triethylamine / tetrahydrofuran / 1 h / 0 °C

With 1H-imidazole; manganese(IV) oxide; lithium aluminium tetrahydride; 2,2,6,6-tetramethylpiperidinyl-lithium; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/ja00222a044

Reference yield:

(2S,3S,4S)-4-isopropenyl-3-methoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (139407-08-2,111563-55-4) → (2S,3S,4S)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-(1-formyl-2-phenylsulfanyl-ethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (103314-30-3,103314-37-0,111563-58-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 100 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / 0 °C

2: 70 percent / imidazole / dimethylformamide / 1.) 0 deg C, 30 min; 2.) r.t., 30 min

3: 97 percent / mCPBA / CH₂Cl₂ / Ambient temperature

4: lithium tetramethylpiperidine / diethyl ether / 1.) 0 deg C, 1 h; 2.) r.t., 1 h

5: 86 percent / MnO₂ / hexane / 1 h / Ambient temperature

6: 93 percent / triethylamine / tetrahydrofuran / 1 h / 0 °C

With 1H-imidazole; manganese(IV) oxide; lithium aluminium tetrahydride; 2,2,6,6-tetramethylpiperidinyl-lithium; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja00222a044

upstream raw materials:

(3S,4S,5S)-2-<1-(tert-butyloxycarbonyl)-4-<2-<(tert-butyldimethylsilyl)oxy>ethyl>-5-<<(tert-butyldimethylsilyl)oxy>methyl>-3-pyrrolidinyl>acrylaldehyde

thiophenol

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

(2S,3S,4S)-4-isopropenyl-3-methoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Downstream raw materials:

(2S,3S,4S)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-((E)-4-hydroxy-1-phenylsulfanylmethyl-but-2-enyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

(2S,3S,4S)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-((E)-4-oxo-1-phenylsulfanylmethyl-pent-2-enyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Acromelic acid A

acromelic acid B