(2S,3R,4R)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-(toluene-4-sulfonyloxy)-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-ethyl ester

Base Information

Chemical Name:(2S,3R,4R)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-(toluene-4-sulfonyloxy)-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-ethyl ester
CAS No.:135388-17-9
Molecular Formula:C₃₀H₄₃NO₈SSi
Molecular Weight:605.825
Hs Code.:

(2S,3R,4R)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-(toluene-4-sulfonyloxy)-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-ethyl ester

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Chemical Property of (2S,3R,4R)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-(toluene-4-sulfonyloxy)-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-ethyl ester

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Technology Process of (2S,3R,4R)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-(toluene-4-sulfonyloxy)-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-ethyl ester

There total 15 articles about (2S,3R,4R)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-(toluene-4-sulfonyloxy)-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-ethyl 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: 86.0%

: (2S,3R,4R)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-hydroxy-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-ethyl ester

: 98-59-9
p-toluenesulfonyl chloride

: 135388-17-9
(2S,3R,4R)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-(toluene-4-sulfonyloxy)-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-ethyl ester

Guidance literature:: With pyridine;
DOI:10.1016/S0040-4039(00)78802-2

Reference yield:

: 13726-69-7,946610-68-0
(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

: 135388-17-9
(2S,3R,4R)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-(toluene-4-sulfonyloxy)-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-ethyl ester

Guidance literature:: Multi-step reaction with 13 steps

1: Et₃N

2: imidazole

3: TFA

4: 1) tBuOCl, 2) Et₃N

5: pyridine

6: 70 percent / TBAF

7: 100 percent / N,N-dimethylaniline

8: 100 percent / nBu₃SnH, AIBN / benzene / Heating

9: DBU / toluene / Heating

10: Jones-oxidation

11: 94 percent / BH₃-Me₂S / tetrahydrofuran / 0 deg C to r.t.

12: 65 percent / Et₃N, DMAP

13: 86 percent / pyridine

With pyridine; 1H-imidazole; dmap; tert-butylhypochlorite; 2,2'-azobis(isobutyronitrile); dimethylsulfide borane complex; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; N,N-dimethyl-aniline; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trifluoroacetic acid; In tetrahydrofuran; toluene; benzene;
DOI:10.1016/S0040-4039(00)78802-2

Reference yield:

: 89813-47-8
N-(tert-butoxycarbonyl)-(2S,4R)-4-hydroxyproline benzyl ester

: 135388-17-9
(2S,3R,4R)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-(toluene-4-sulfonyloxy)-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-ethyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: imidazole

2: TFA

3: 1) tBuOCl, 2) Et₃N

4: pyridine

5: 70 percent / TBAF

6: 100 percent / N,N-dimethylaniline

7: 100 percent / nBu₃SnH, AIBN / benzene / Heating

8: DBU / toluene / Heating

9: Jones-oxidation

10: 94 percent / BH₃-Me₂S / tetrahydrofuran / 0 deg C to r.t.

11: 65 percent / Et₃N, DMAP

12: 86 percent / pyridine

With pyridine; 1H-imidazole; dmap; tert-butylhypochlorite; 2,2'-azobis(isobutyronitrile); dimethylsulfide borane complex; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; N,N-dimethyl-aniline; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trifluoroacetic acid; In tetrahydrofuran; toluene; benzene;
DOI:10.1016/S0040-4039(00)78802-2