(3S)-3-[(2R,3S)-3-tert-butyldiphenylsiloxy-4,4-dimethyloxolan-2-yloxy]-2-methyl-1-(2-methyl-1,3-thiazol-4-yl)hexa-(1E,5)-diene

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Chemical Name:(3S)-3-[(2R,3S)-3-tert-butyldiphenylsiloxy-4,4-dimethyloxolan-2-yloxy]-2-methyl-1-(2-methyl-1,3-thiazol-4-yl)hexa-(1E,5)-diene
CAS No.:924961-41-1
Molecular Formula:C₃₃H₄₃NO₃SSi
Molecular Weight:561.861
Hs Code.:

Synonyms:(3S)-3-[(2R,3S)-3-tert-butyldiphenylsiloxy-4,4-dimethyloxolan-2-yloxy]-2-methyl-1-(2-methyl-1,3-thiazol-4-yl)hexa-(1E,5)-diene

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Chemical Property of (3S)-3-[(2R,3S)-3-tert-butyldiphenylsiloxy-4,4-dimethyloxolan-2-yloxy]-2-methyl-1-(2-methyl-1,3-thiazol-4-yl)hexa-(1E,5)-diene

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Technology Process of (3S)-3-[(2R,3S)-3-tert-butyldiphenylsiloxy-4,4-dimethyloxolan-2-yloxy]-2-methyl-1-(2-methyl-1,3-thiazol-4-yl)hexa-(1E,5)-diene

There total 7 articles about (3S)-3-[(2R,3S)-3-tert-butyldiphenylsiloxy-4,4-dimethyloxolan-2-yloxy]-2-methyl-1-(2-methyl-1,3-thiazol-4-yl)hexa-(1E,5)-diene 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: 99.0%

: 924961-40-0
(3S)-3-[(2R,3S)-3-tert-butyldiphenylsiloxy-4,4-dimethyloxolan-2-yl]oxy-5-hexen-2-one

: 63928-37-0
diethyl (2-methyl-1,3-thiazol-4-yl)methylphosphonate

: 924961-41-1
(3S)-3-[(2R,3S)-3-tert-butyldiphenylsiloxy-4,4-dimethyloxolan-2-yloxy]-2-methyl-1-(2-methyl-1,3-thiazol-4-yl)hexa-(1E,5)-diene

Guidance literature:: diethyl (2-methyl-1,3-thiazol-4-yl)methylphosphonate; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.5h;

(3S)-3-[(2R,3S)-3-tert-butyldiphenylsiloxy-4,4-dimethyloxolan-2-yl]oxy-5-hexen-2-one; at 20 ℃; for 15h;
DOI:10.1021/jo0618573

Reference yield:

: 924961-36-4
(2S)-2-tert-butyldiphenylsiloxy-3,3-dimethyl-4-butanolide

: 924961-41-1
(3S)-3-[(2R,3S)-3-tert-butyldiphenylsiloxy-4,4-dimethyloxolan-2-yloxy]-2-methyl-1-(2-methyl-1,3-thiazol-4-yl)hexa-(1E,5)-diene

Guidance literature:: Multi-step reaction with 5 steps

1.1: 77 percent / DIBAL-H / toluene / 1 h / -78 °C

2.1: 96 percent / Et₃N; 4-(dimethylamino)pyridine / tetrahydrofuran / 1 h / 20 °C

3.1: 73 percent / BF₃*OEt₂ / CH₂Cl₂ / 4.5 h / -78 - -10 °C

4.1: NaH / tetrahydrofuran / 0.08 h / 0 °C

4.2: 52 percent / tetrahydrofuran / 15 h / 20 °C

5.1: NaHMDS / tetrahydrofuran / 0.5 h / -78 °C

5.2: 99 percent / 15 h / 20 °C

With dmap; boron trifluoride diethyl etherate; sodium hexamethyldisilazane; sodium hydride; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; dichloromethane; toluene; 5.2: Wadsworth-Emmons reaction;
DOI:10.1021/jo0618573

Reference yield:

: 924961-42-2
(2S)-3-tert-butyldiphenylsiloxy-2-hydroxy-4,4-dimethyloxolane

: 924961-41-1
(3S)-3-[(2R,3S)-3-tert-butyldiphenylsiloxy-4,4-dimethyloxolan-2-yloxy]-2-methyl-1-(2-methyl-1,3-thiazol-4-yl)hexa-(1E,5)-diene

Guidance literature:: Multi-step reaction with 4 steps

1.1: 96 percent / Et₃N; 4-(dimethylamino)pyridine / tetrahydrofuran / 1 h / 20 °C

2.1: 73 percent / BF₃*OEt₂ / CH₂Cl₂ / 4.5 h / -78 - -10 °C

3.1: NaH / tetrahydrofuran / 0.08 h / 0 °C

3.2: 52 percent / tetrahydrofuran / 15 h / 20 °C

4.1: NaHMDS / tetrahydrofuran / 0.5 h / -78 °C

4.2: 99 percent / 15 h / 20 °C

With dmap; boron trifluoride diethyl etherate; sodium hexamethyldisilazane; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane; 4.2: Wadsworth-Emmons reaction;
DOI:10.1021/jo0618573