(3S,4R)-4-[(2S,6R)-2-[(S)-(1-allyloxycarbonyl)pyrrolidin-2-ylmethylthiomethyl]cyclohexanon-6-yl]-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one

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Chemical Name:(3S,4R)-4-[(2S,6R)-2-[(S)-(1-allyloxycarbonyl)pyrrolidin-2-ylmethylthiomethyl]cyclohexanon-6-yl]-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one
CAS No.:211945-21-0
Molecular Formula:C₂₇H₄₆N₂O₅SSi
Molecular Weight:538.824
Hs Code.:

(3S,4R)-4-[(2S,6R)-2-[(S)-(1-allyloxycarbonyl)pyrrolidin-2-ylmethylthiomethyl]cyclohexanon-6-yl]-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one

Synonyms:(3S,4R)-4-[(2S,6R)-2-[(S)-(1-allyloxycarbonyl)pyrrolidin-2-ylmethylthiomethyl]cyclohexanon-6-yl]-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one

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Chemical Property of (3S,4R)-4-[(2S,6R)-2-[(S)-(1-allyloxycarbonyl)pyrrolidin-2-ylmethylthiomethyl]cyclohexanon-6-yl]-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one

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Technology Process of (3S,4R)-4-[(2S,6R)-2-[(S)-(1-allyloxycarbonyl)pyrrolidin-2-ylmethylthiomethyl]cyclohexanon-6-yl]-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one

There total 2 articles about (3S,4R)-4-[(2S,6R)-2-[(S)-(1-allyloxycarbonyl)pyrrolidin-2-ylmethylthiomethyl]cyclohexanon-6-yl]-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one 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: 37.0%

: (S)-1-allyloxycarbonyl-2-mercaptomethylpyrrolidine

: 276240-40-5
Methanesulfonic acid (1R,3R)-3-{(2R,3S)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-oxo-cyclohexylmethyl ester

: 211945-22-1
(3S,4R)-4-[(2R,6R)-2-[(S)-(1-allyloxycarbonyl)pyrrolidin-2-ylmethylthiomethyl]cyclohexanon-6-yl]-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one

: 211945-21-0
(3S,4R)-4-[(2S,6R)-2-[(S)-(1-allyloxycarbonyl)pyrrolidin-2-ylmethylthiomethyl]cyclohexanon-6-yl]-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one

Guidance literature:: Methanesulfonic acid (1R,3R)-3-{(2R,3S)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-oxo-cyclohexylmethyl ester; With triethylamine; In N,N-dimethyl-formamide; at 20 ℃;

(S)-1-allyloxycarbonyl-2-mercaptomethylpyrrolidine; With triethylamine; In N,N-dimethyl-formamide; at 20 - 40 ℃; for 5h;
DOI:10.7164/antibiotics.53.404

Reference yield:

: 211945-46-9
(3S,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(2R,6R)-2-(hydroxymethyl)cyclohexanon-6-yl]azetidin-2-one

: 211945-21-0
(3S,4R)-4-[(2S,6R)-2-[(S)-(1-allyloxycarbonyl)pyrrolidin-2-ylmethylthiomethyl]cyclohexanon-6-yl]-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: Et₃N / tetrahydrofuran / 2 h / ice-cooling

2.1: Et₃N / dimethylformamide / 20 °C

2.2: 26 percent / Et₃N / dimethylformamide / 5 h / 20 - 40 °C

With triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide; 1.1: mesylation / 2.1: Elimination / 2.2: Addition;
DOI:10.7164/antibiotics.53.404