(+/-)-methyl N-benzoyl-α-(E)-(2'-fluoro-2'-benzenesulfonyl)vinyl-[3'',4''-bis(tert-butyldimethylsilyloxy)]phenylalaninate

Base Information

Chemical Name:(+/-)-methyl N-benzoyl-α-(E)-(2'-fluoro-2'-benzenesulfonyl)vinyl-[3'',4''-bis(tert-butyldimethylsilyloxy)]phenylalaninate
CAS No.:714222-61-4
Molecular Formula:C₃₇H₅₀FNO₇SSi₂
Molecular Weight:728.042
Hs Code.:

Synonyms:(+/-)-methyl N-benzoyl-α-(E)-(2'-fluoro-2'-benzenesulfonyl)vinyl-[3'',4''-bis(tert-butyldimethylsilyloxy)]phenylalaninate

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Chemical Property of (+/-)-methyl N-benzoyl-α-(E)-(2'-fluoro-2'-benzenesulfonyl)vinyl-[3'',4''-bis(tert-butyldimethylsilyloxy)]phenylalaninate

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Technology Process of (+/-)-methyl N-benzoyl-α-(E)-(2'-fluoro-2'-benzenesulfonyl)vinyl-[3'',4''-bis(tert-butyldimethylsilyloxy)]phenylalaninate

There total 2 articles about (+/-)-methyl N-benzoyl-α-(E)-(2'-fluoro-2'-benzenesulfonyl)vinyl-[3'',4''-bis(tert-butyldimethylsilyloxy)]phenylalaninate 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: 57.0%

: 135789-87-6,114968-97-7
phosphonic acid diethyl ester

: 714222-55-6
(+/-)-methyl N-benzoyl-α-formyl-3',4'-bis(tert-butyldimethylsilyloxy)phenylalaninate

: 152774-26-0
Methyl N-benzoyl-3',4'bis<(tert-butyldimethylsilyl)oxy>phenylalaninate

: 714222-61-4
(+/-)-methyl N-benzoyl-α-(E)-(2'-fluoro-2'-benzenesulfonyl)vinyl-[3'',4''-bis(tert-butyldimethylsilyloxy)]phenylalaninate

Guidance literature:: phosphonic acid diethyl ester; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.5h;

(+/-)-methyl N-benzoyl-α-formyl-3',4'-bis(tert-butyldimethylsilyloxy)phenylalaninate; In tetrahydrofuran; at -78 - 20 ℃;
DOI:10.1021/ol049422u

Reference yield:

: 152774-42-0
Methyl N-benzoyl-2-vinyl-3',4'-bis<(tert-butyldimethylsilyl)oxy>phenylalaninate

: 714222-61-4
(+/-)-methyl N-benzoyl-α-(E)-(2'-fluoro-2'-benzenesulfonyl)vinyl-[3'',4''-bis(tert-butyldimethylsilyloxy)]phenylalaninate

Guidance literature:: Multi-step reaction with 2 steps

1.1: ozone / CH₂Cl₂ / -78 °C

1.2: 99 percent / acetic acid; Zn / CH₂Cl₂ / Heating

2.1: LiHMDS / tetrahydrofuran / 0.5 h / -78 °C

2.2: 57 percent / tetrahydrofuran / -78 - 20 °C

With ozone; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol049422u

Reference yield:

: 714222-61-4
(+/-)-methyl N-benzoyl-α-(E)-(2'-fluoro-2'-benzenesulfonyl)vinyl-[3'',4''-bis(tert-butyldimethylsilyloxy)]phenylalaninate

: (+/-)-(Z)-α-(2'-fluoro)vinyl-3'',4''-dihydroxyphenylalanine hydrochloride

Guidance literature:: (+/-)-methyl N-benzoyl-α-(E)-(2'-fluoro-2'-benzenesulfonyl)vinyl-[3'',4''-bis(tert-butyldimethylsilyloxy)]phenylalaninate; With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; Heating;

With hydrogenchloride; for 15h; Heating;
DOI:10.1021/ol049422u