tert-Butyl-[(2S,3R,4aS,8aS,9aR,10aR)-2-((R)-3-chloro-2-methyl-3-phenylsulfanyl-propyl)-4a,5-dimethyl-3,4,4a,7,8a,9,9a,10a-octahydro-2H-1,8,10-trioxa-anthracen-3-yloxy]-dimethyl-silane

Base Information

Chemical Name:tert-Butyl-[(2S,3R,4aS,8aS,9aR,10aR)-2-((R)-3-chloro-2-methyl-3-phenylsulfanyl-propyl)-4a,5-dimethyl-3,4,4a,7,8a,9,9a,10a-octahydro-2H-1,8,10-trioxa-anthracen-3-yloxy]-dimethyl-silane
CAS No.:889109-13-1
Molecular Formula:C₂₉H₄₅ClO₄SSi
Molecular Weight:553.278
Hs Code.:

tert-Butyl-[(2S,3R,4aS,8aS,9aR,10aR)-2-((R)-3-chloro-2-methyl-3-phenylsulfanyl-propyl)-4a,5-dimethyl-3,4,4a,7,8a,9,9a,10a-octahydro-2H-1,8,10-trioxa-anthracen-3-yloxy]-dimethyl-silane

Synonyms:tert-Butyl-[(2S,3R,4aS,8aS,9aR,10aR)-2-((R)-3-chloro-2-methyl-3-phenylsulfanyl-propyl)-4a,5-dimethyl-3,4,4a,7,8a,9,9a,10a-octahydro-2H-1,8,10-trioxa-anthracen-3-yloxy]-dimethyl-silane

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Chemical Property of tert-Butyl-[(2S,3R,4aS,8aS,9aR,10aR)-2-((R)-3-chloro-2-methyl-3-phenylsulfanyl-propyl)-4a,5-dimethyl-3,4,4a,7,8a,9,9a,10a-octahydro-2H-1,8,10-trioxa-anthracen-3-yloxy]-dimethyl-silane

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Technology Process of tert-Butyl-[(2S,3R,4aS,8aS,9aR,10aR)-2-((R)-3-chloro-2-methyl-3-phenylsulfanyl-propyl)-4a,5-dimethyl-3,4,4a,7,8a,9,9a,10a-octahydro-2H-1,8,10-trioxa-anthracen-3-yloxy]-dimethyl-silane

There total 13 articles about tert-Butyl-[(2S,3R,4aS,8aS,9aR,10aR)-2-((R)-3-chloro-2-methyl-3-phenylsulfanyl-propyl)-4a,5-dimethyl-3,4,4a,7,8a,9,9a,10a-octahydro-2H-1,8,10-trioxa-anthracen-3-yloxy]-dimethyl-silane 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:

: 889109-12-0
tert-Butyl-[(2S,3R,4aS,8aS,9aR,10aR)-4a,5-dimethyl-2-((R)-2-methyl-3-phenylsulfanyl-propyl)-3,4,4a,7,8a,9,9a,10a-octahydro-2H-1,8,10-trioxa-anthracen-3-yloxy]-dimethyl-silane

: 889109-13-1
tert-Butyl-[(2S,3R,4aS,8aS,9aR,10aR)-2-((R)-3-chloro-2-methyl-3-phenylsulfanyl-propyl)-4a,5-dimethyl-3,4,4a,7,8a,9,9a,10a-octahydro-2H-1,8,10-trioxa-anthracen-3-yloxy]-dimethyl-silane

Guidance literature:: With N-chloro-succinimide; In tetrachloromethane; dichloromethane; at 20 ℃; for 0.5h;
DOI:10.1021/jo0603025

Reference yield:

: 858346-53-9
(2R,4aR,6R,7S,8aR,9aS,10aS)-6-(tert-Butyl-dimethyl-silanyloxy)-7-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-10a-methyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracene

: 889109-13-1
tert-Butyl-[(2S,3R,4aS,8aS,9aR,10aR)-2-((R)-3-chloro-2-methyl-3-phenylsulfanyl-propyl)-4a,5-dimethyl-3,4,4a,7,8a,9,9a,10a-octahydro-2H-1,8,10-trioxa-anthracen-3-yloxy]-dimethyl-silane

Guidance literature:: Multi-step reaction with 13 steps

1.1: H₂ / Pd(OH)2/C / ethyl acetate / 4 h

2.1: 77 percent / KH / tetrahydrofuran / 2 h / 35 °C

3.1: 100 percent / HMDS; TMSI / CH₂Cl₂ / 1 h / 0 °C

4.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

5.1: tetrahydrofuran / 0.5 h / 0 °C

6.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

7.1: NaHMDS / tetrahydrofuran / 0 °C

7.2: 298 mg / tetrahydrofuran / 1 h / 20 °C

8.1: 84 percent / DDQ; aq. NaHCO₃ / CH₂Cl₂ / 1.5 h / 45 °C

9.1: KH / tetrahydrofuran / 1 h / 0 °C

10.1: 176 mg / (PCy₃)2Cl₂Ru=CHPh / CH₂Cl₂ / 20 h / 20 °C

11.1: 95 percent / CSA / methanol; CH₂Cl₂ / 2.5 h / 0 °C

12.1: 95 percent / Bu₃P / dimethylformamide / 4 h / 20 °C

13.1: NCS / CCl₄; CH₂Cl₂ / 0.5 h / 20 °C

With N-chloro-succinimide; Grubbs catalyst first generation; oxalyl dichloride; trimethylsilyl iodide; tributylphosphine; camphor-10-sulfonic acid; hydrogen; sodium hexamethyldisilazane; potassium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium dihydroxide; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 4.1: Swern oxidation / 5.1: Grignard reaction / 6.1: Swern oxidation / 7.2: Wittig reaction;
DOI:10.1021/jo0603025

Reference yield:

: 889109-11-9
(R)-3-[(2S,3R,4aS,8aS,9aR,10aR)-3-(tert-Butyl-dimethyl-silanyloxy)-4a,5-dimethyl-3,4,4a,7,8a,9,9a,10a-octahydro-2H-1,8,10-trioxa-anthracen-2-yl]-2-methyl-propan-1-ol

: 889109-13-1
tert-Butyl-[(2S,3R,4aS,8aS,9aR,10aR)-2-((R)-3-chloro-2-methyl-3-phenylsulfanyl-propyl)-4a,5-dimethyl-3,4,4a,7,8a,9,9a,10a-octahydro-2H-1,8,10-trioxa-anthracen-3-yloxy]-dimethyl-silane

Guidance literature:: Multi-step reaction with 2 steps

1: 95 percent / Bu₃P / dimethylformamide / 4 h / 20 °C

2: NCS / CCl₄; CH₂Cl₂ / 0.5 h / 20 °C

With N-chloro-succinimide; tributylphosphine; In tetrachloromethane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo0603025