(+/-)-methyl N-benzoyl-α-(E)-(2'-fluoro-2'-benzenesulfonyl)vinyl-(3''-O-tert-butyldimethylsilyl)-m-tyrosinate

Base Information

Chemical Name:(+/-)-methyl N-benzoyl-α-(E)-(2'-fluoro-2'-benzenesulfonyl)vinyl-(3''-O-tert-butyldimethylsilyl)-m-tyrosinate
CAS No.:714222-60-3
Molecular Formula:C₃₁H₃₆FNO₆SSi
Molecular Weight:597.78
Hs Code.:

Synonyms:(+/-)-methyl N-benzoyl-α-(E)-(2'-fluoro-2'-benzenesulfonyl)vinyl-(3''-O-tert-butyldimethylsilyl)-m-tyrosinate

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Chemical Property of (+/-)-methyl N-benzoyl-α-(E)-(2'-fluoro-2'-benzenesulfonyl)vinyl-(3''-O-tert-butyldimethylsilyl)-m-tyrosinate

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Technology Process of (+/-)-methyl N-benzoyl-α-(E)-(2'-fluoro-2'-benzenesulfonyl)vinyl-(3''-O-tert-butyldimethylsilyl)-m-tyrosinate

There total 4 articles about (+/-)-methyl N-benzoyl-α-(E)-(2'-fluoro-2'-benzenesulfonyl)vinyl-(3''-O-tert-butyldimethylsilyl)-m-tyrosinate 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: 55.0%

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

: 714222-54-5
(+/-)-methyl N-benzoyl-α-formyl-(3'-O-tert-butyldimethylsilyl)-m-tyrosinate

: 2-benzoylamino-3-[3-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid methyl ester

: 714222-60-3
(+/-)-methyl N-benzoyl-α-(E)-(2'-fluoro-2'-benzenesulfonyl)vinyl-(3''-O-tert-butyldimethylsilyl)-m-tyrosinate

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

(+/-)-methyl N-benzoyl-α-formyl-(3'-O-tert-butyldimethylsilyl)-m-tyrosinate; In tetrahydrofuran; at -78 - 20 ℃;
DOI:10.1021/ol049422u

Reference yield:

: 60027-58-9
(Z)-α-N-benzoylamino-2-butenoic acid methylester

: 714222-60-3
(+/-)-methyl N-benzoyl-α-(E)-(2'-fluoro-2'-benzenesulfonyl)vinyl-(3''-O-tert-butyldimethylsilyl)-m-tyrosinate

Guidance literature:: Multi-step reaction with 3 steps

1.1: lithium diisopropylamide; HMPA / hexane; tetrahydrofuran / 0.08 h / -78 °C

1.2: 70 percent / hexane; tetrahydrofuran / 1 h / -78 °C

2.1: ozone / CH₂Cl₂ / -78 °C

2.2: 66 percent / acetic acid; Zn / CH₂Cl₂ / Heating

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

3.2: 55 percent / tetrahydrofuran / -78 - 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; ozone; lithium hexamethyldisilazane; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/ol049422u

Reference yield:

: 131362-25-9
[3-(bromomethyl)-phenoxy]dimethyl(1,1-dimethylethyl)silane

: 714222-60-3
(+/-)-methyl N-benzoyl-α-(E)-(2'-fluoro-2'-benzenesulfonyl)vinyl-(3''-O-tert-butyldimethylsilyl)-m-tyrosinate

Guidance literature:: Multi-step reaction with 3 steps

1.1: lithium diisopropylamide; HMPA / hexane; tetrahydrofuran / 0.08 h / -78 °C

1.2: 70 percent / hexane; tetrahydrofuran / 1 h / -78 °C

2.1: ozone / CH₂Cl₂ / -78 °C

2.2: 66 percent / acetic acid; Zn / CH₂Cl₂ / Heating

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

3.2: 55 percent / tetrahydrofuran / -78 - 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; ozone; lithium hexamethyldisilazane; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/ol049422u