(3R,5R,6R,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-4,4,6,8-tetramethyl-5-triphenylsilanyloxy-tridec-12-enoic acid (S)-1-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-but-3-enyl ester

Base Information

Chemical Name:(3R,5R,6R,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-4,4,6,8-tetramethyl-5-triphenylsilanyloxy-tridec-12-enoic acid (S)-1-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-but-3-enyl ester
CAS No.:188259-71-4
Molecular Formula:C₅₂H₇₃NO₅SSi₂
Molecular Weight:880.392
Hs Code.:

(3R,5R,6R,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-4,4,6,8-tetramethyl-5-triphenylsilanyloxy-tridec-12-enoic acid (S)-1-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-but-3-enyl ester

Synonyms:(3R,5R,6R,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-4,4,6,8-tetramethyl-5-triphenylsilanyloxy-tridec-12-enoic acid (S)-1-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-but-3-enyl ester

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Chemical Property of (3R,5R,6R,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-4,4,6,8-tetramethyl-5-triphenylsilanyloxy-tridec-12-enoic acid (S)-1-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-but-3-enyl ester

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Technology Process of (3R,5R,6R,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-4,4,6,8-tetramethyl-5-triphenylsilanyloxy-tridec-12-enoic acid (S)-1-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-but-3-enyl ester

There total 19 articles about (3R,5R,6R,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-4,4,6,8-tetramethyl-5-triphenylsilanyloxy-tridec-12-enoic acid (S)-1-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-but-3-enyl 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:

: 188259-62-3
(1S)-[(1E)-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethynyl]-3-butenyl acetate

: 188259-66-7
(3R,4R,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-2,2,4,6-tetramethyl-3-triphenylsilanyloxy-undec-10-enal

: 188259-71-4
(3R,5R,6R,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-4,4,6,8-tetramethyl-5-triphenylsilanyloxy-tridec-12-enoic acid (S)-1-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-but-3-enyl ester

: 188259-68-9
(3S,5R,6R,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-4,4,6,8-tetramethyl-5-triphenylsilanyloxy-tridec-12-enoic acid (S)-1-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-but-3-enyl ester

Guidance literature:: With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃;
DOI:10.1021/ja964275j

Reference yield:

: 184246-38-6
(E)-2-methyl-3-(2-methylthiazol-4-yl)acrylaldehyde

: 188259-71-4
(3R,5R,6R,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-4,4,6,8-tetramethyl-5-triphenylsilanyloxy-tridec-12-enoic acid (S)-1-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-but-3-enyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: (S)-(-)-BINOL; Ti(Oi-Pr)4 / CH₂Cl₂ / -20 °C

2: 95 percent / Et₃N; 4-DMAP / CH₂Cl₂ / 20 °C

3: LDA / tetrahydrofuran / -78 °C

With titanium(IV) isopropylate; dmap; (S)-[1,1']-binaphthalenyl-2,2'-diol; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; 1: allylation / 2: Acetylation / 3: Condensation;
DOI:10.1021/ja964275j

Reference yield:

: 186692-60-4
(2R,3R,4R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-6-[1,3]dithian-2-yl-2,4,6-trimethyl-5-triphenylsilanyloxy-heptanal

: 188259-71-4
(3R,5R,6R,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-4,4,6,8-tetramethyl-5-triphenylsilanyloxy-tridec-12-enoic acid (S)-1-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-but-3-enyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 92 percent / diethyl ether / -78 - 0 °C

3: LDA / tetrahydrofuran / -78 °C

With lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; 1: Grignard reaction / 3: Condensation;
DOI:10.1021/ja964275j