(3S,5S)-5-{Allyl-[(Z)-2-(tert-butyl-dimethyl-silanyloxy)-2-(3-methoxy-phenyl)-vinyl]-carbamoyl}-2-methoxy-3-methoxymethoxymethyl-pyrrolidine-1-carboxylic acid benzyl ester

Base Information

Chemical Name:(3S,5S)-5-{Allyl-[(Z)-2-(tert-butyl-dimethyl-silanyloxy)-2-(3-methoxy-phenyl)-vinyl]-carbamoyl}-2-methoxy-3-methoxymethoxymethyl-pyrrolidine-1-carboxylic acid benzyl ester
CAS No.:129416-09-7
Molecular Formula:C₃₅H₅₀N₂O₈Si
Molecular Weight:654.876
Hs Code.:

(3S,5S)-5-{Allyl-[(Z)-2-(tert-butyl-dimethyl-silanyloxy)-2-(3-methoxy-phenyl)-vinyl]-carbamoyl}-2-methoxy-3-methoxymethoxymethyl-pyrrolidine-1-carboxylic acid benzyl ester

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Chemical Property of (3S,5S)-5-{Allyl-[(Z)-2-(tert-butyl-dimethyl-silanyloxy)-2-(3-methoxy-phenyl)-vinyl]-carbamoyl}-2-methoxy-3-methoxymethoxymethyl-pyrrolidine-1-carboxylic acid benzyl ester

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Technology Process of (3S,5S)-5-{Allyl-[(Z)-2-(tert-butyl-dimethyl-silanyloxy)-2-(3-methoxy-phenyl)-vinyl]-carbamoyl}-2-methoxy-3-methoxymethoxymethyl-pyrrolidine-1-carboxylic acid benzyl ester

There total 16 articles about (3S,5S)-5-{Allyl-[(Z)-2-(tert-butyl-dimethyl-silanyloxy)-2-(3-methoxy-phenyl)-vinyl]-carbamoyl}-2-methoxy-3-methoxymethoxymethyl-pyrrolidine-1-carboxylic acid benzyl 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:

: (3S,5S)-5-{Allyl-[2-(3-methoxy-phenyl)-2-oxo-ethyl]-carbamoyl}-2-methoxy-3-methoxymethoxymethyl-pyrrolidine-1-carboxylic acid benzyl ester

: 18162-48-6
tert-butyldimethylsilyl chloride

: 129416-09-7,129416-10-0,129416-24-6,129416-25-7
(3S,5S)-5-{Allyl-[(Z)-2-(tert-butyl-dimethyl-silanyloxy)-2-(3-methoxy-phenyl)-vinyl]-carbamoyl}-2-methoxy-3-methoxymethoxymethyl-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:: With potassium hydride; In tetrahydrofuran; triethylamine; at 0 ℃; Yield given;
DOI:10.1016/0040-4039(90)80083-X

Reference yield:

: 27382-18-9
2-amino-1-(3-methoxyphenyl)ethanol

: 129416-09-7,129416-10-0,129416-24-6,129416-25-7
(3S,5S)-5-{Allyl-[(Z)-2-(tert-butyl-dimethyl-silanyloxy)-2-(3-methoxy-phenyl)-vinyl]-carbamoyl}-2-methoxy-3-methoxymethoxymethyl-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 14 steps

1: 93 percent / pyridine / CH₂Cl₂ / 0 °C

2: 90 percent / KH / tetrahydrofuran

3: 4 N NaOH / ethanol / Heating

4: DMAP, iPr₂NEt / CH₂Cl₂

5: 96 percent / NEt₃ / CH₂Cl₂ / 0 °C

6: tetrahydrofuran / 60 °C

7: 1 N HCl / tetrahydrofuran

8: 91 percent / sodium cyanoborohydride / ethanol; tetrahydrofuran; acetic acid / -20 deg C to room temperature

9: 88 percent / iPrNEt₂ / CH₂Cl₂

10: RedAl / tetrahydrofuran / -78 to -50 deg C

11: PPTS

12: Bu₄NF / tetrahydrofuran

13: Swern oxidation

14: KH / tetrahydrofuran; triethylamine / 0 °C

With pyridine; hydrogenchloride; dmap; sodium hydroxide; N,N-diethyl-N-isopropylamine; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; potassium hydride; sodium cyanoborohydride; triethylamine; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; ethanol; dichloromethane; acetic acid; triethylamine;
DOI:10.1016/0040-4039(90)80083-X

Reference yield:

: 129416-01-9
5-(3-Methoxy-phenyl)-oxazolidin-2-one

: 129416-09-7,129416-10-0,129416-24-6,129416-25-7
(3S,5S)-5-{Allyl-[(Z)-2-(tert-butyl-dimethyl-silanyloxy)-2-(3-methoxy-phenyl)-vinyl]-carbamoyl}-2-methoxy-3-methoxymethoxymethyl-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 13 steps

1: 90 percent / KH / tetrahydrofuran

2: 4 N NaOH / ethanol / Heating

3: DMAP, iPr₂NEt / CH₂Cl₂

4: 96 percent / NEt₃ / CH₂Cl₂ / 0 °C

5: tetrahydrofuran / 60 °C

6: 1 N HCl / tetrahydrofuran

7: 91 percent / sodium cyanoborohydride / ethanol; tetrahydrofuran; acetic acid / -20 deg C to room temperature

8: 88 percent / iPrNEt₂ / CH₂Cl₂

9: RedAl / tetrahydrofuran / -78 to -50 deg C

10: PPTS

11: Bu₄NF / tetrahydrofuran

12: Swern oxidation

13: KH / tetrahydrofuran; triethylamine / 0 °C

With hydrogenchloride; dmap; sodium hydroxide; N,N-diethyl-N-isopropylamine; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; potassium hydride; sodium cyanoborohydride; triethylamine; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; ethanol; dichloromethane; acetic acid; triethylamine;
DOI:10.1016/0040-4039(90)80083-X