pyrrolidine-1,2-dicarboxylic acid (2S)-2-[(1S,3S,5S,6S,8R)-8-benzoyloxy-1-tert-butyl-5-(tert-butyldimethylsilyloxy)-3,6-dimethyl-7-oxononyl] ester 1-tert-butyl ester

Base Information

Chemical Name:pyrrolidine-1,2-dicarboxylic acid (2S)-2-[(1S,3S,5S,6S,8R)-8-benzoyloxy-1-tert-butyl-5-(tert-butyldimethylsilyloxy)-3,6-dimethyl-7-oxononyl] ester 1-tert-butyl ester
CAS No.:582321-75-3
Molecular Formula:C₃₈H₆₃NO₈Si
Molecular Weight:690.006
Hs Code.:

pyrrolidine-1,2-dicarboxylic acid (2S)-2-[(1S,3S,5S,6S,8R)-8-benzoyloxy-1-tert-butyl-5-(tert-butyldimethylsilyloxy)-3,6-dimethyl-7-oxononyl] ester 1-tert-butyl ester

Synonyms:pyrrolidine-1,2-dicarboxylic acid (2S)-2-[(1S,3S,5S,6S,8R)-8-benzoyloxy-1-tert-butyl-5-(tert-butyldimethylsilyloxy)-3,6-dimethyl-7-oxononyl] ester 1-tert-butyl ester

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Chemical Property of pyrrolidine-1,2-dicarboxylic acid (2S)-2-[(1S,3S,5S,6S,8R)-8-benzoyloxy-1-tert-butyl-5-(tert-butyldimethylsilyloxy)-3,6-dimethyl-7-oxononyl] ester 1-tert-butyl ester

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Technology Process of pyrrolidine-1,2-dicarboxylic acid (2S)-2-[(1S,3S,5S,6S,8R)-8-benzoyloxy-1-tert-butyl-5-(tert-butyldimethylsilyloxy)-3,6-dimethyl-7-oxononyl] ester 1-tert-butyl ester

There total 20 articles about pyrrolidine-1,2-dicarboxylic acid (2S)-2-[(1S,3S,5S,6S,8R)-8-benzoyloxy-1-tert-butyl-5-(tert-butyldimethylsilyloxy)-3,6-dimethyl-7-oxononyl] ester 1-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: 78.0%

: Benzoic acid (1R,3S,4S,6R,8S)-4-(tert-butyl-dimethyl-silanyloxy)-8-hydroxy-1,3,6,9,9-pentamethyl-2-oxo-decyl ester

: 15761-39-4,59433-50-0
1-(tert-butoxycarbonyl)-L-proline

: 582321-75-3
pyrrolidine-1,2-dicarboxylic acid (2S)-2-[(1S,3S,5S,6S,8R)-8-benzoyloxy-1-tert-butyl-5-(tert-butyldimethylsilyloxy)-3,6-dimethyl-7-oxononyl] ester 1-tert-butyl ester

Guidance literature:: 1-(tert-butoxycarbonyl)-L-proline; With 2,4,6-trichlorobenzoyl chloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 ℃; for 10h;

Benzoic acid (1R,3S,4S,6R,8S)-4-(tert-butyl-dimethyl-silanyloxy)-8-hydroxy-1,3,6,9,9-pentamethyl-2-oxo-decyl ester; With dmap; In toluene; at 20 ℃; for 3h;
DOI:10.1021/ol052907d

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 582321-74-2
(S)-Pyrrolidine-1,2-dicarboxylic acid 2-((1S,3S,5S,6S,8R)-8-benzoyloxy-1-tert-butyl-5-hydroxy-3,6-dimethyl-7-oxo-nonyl) ester 1-tert-butyl ester

: 582321-75-3
pyrrolidine-1,2-dicarboxylic acid (2S)-2-[(1S,3S,5S,6S,8R)-8-benzoyloxy-1-tert-butyl-5-(tert-butyldimethylsilyloxy)-3,6-dimethyl-7-oxononyl] ester 1-tert-butyl ester

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at -50 ℃; for 2h;
DOI:10.1021/ja036050w

Reference yield:

: 878626-87-0
(S)-5,5-dimethyl-4-(4-methoxybenzyloxy)-2-hexanone

: 582321-75-3
pyrrolidine-1,2-dicarboxylic acid (2S)-2-[(1S,3S,5S,6S,8R)-8-benzoyloxy-1-tert-butyl-5-(tert-butyldimethylsilyloxy)-3,6-dimethyl-7-oxononyl] ester 1-tert-butyl ester

Guidance literature:: Multi-step reaction with 10 steps

1.1: tetrahydrofuran / 0.5 h / 0 °C

2.1: pyridine; DMAP / 24 h / 50 °C

3.1: PdCl₂(CH₃CN)2 / tetrahydrofuran / 2 h / 20 °C

4.1: 3.29 g / K₂CO₃ / methanol / 1.5 h / 0 °C

5.1: 100 percent / H₂ / Ru(OAc)2[(S)-binap] / methanol / 24 h / 50 °C

6.1: 96 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

7.1: (c-hex)2BCl; Me₂NEt / diethyl ether / 15 h / -78 - -20 °C

8.1: 894 mg / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

9.1: DDQ / CH₂Cl₂; H₂O / 0.5 h / 0 °C / pH 7

10.1: iPr₂NEt; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 10 h / 20 °C

10.2: 78 percent / DMAP / toluene / 3 h / 20 °C

With pyridine; 2,6-dimethylpyridine; dmap; oxalyl dichloride; N,N-dimethyl-ethanamine; 2,4,6-trichlorobenzoyl chloride; dicyclohexylboron chloride; hydrogen; potassium carbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; dichloro bis(acetonitrile) palladium(II); Ru(OCOCH₃)2{(S)-2,2'-bis(diphenylphosphino)-1,1'-dinaphthyl)}; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; 6.1: Swern oxidation / 7.1: aldol reaction;
DOI:10.1021/ol052907d