[(R)-1-((4E,10Z)-(2R,6R,8S,9S)-9-Benzyloxy-6,8,10-trimethyl-thiacycloundeca-4,10-dien-2-yl)-propoxy]-tert-butyl-dimethyl-silane

Base Information

Chemical Name:[(R)-1-((4E,10Z)-(2R,6R,8S,9S)-9-Benzyloxy-6,8,10-trimethyl-thiacycloundeca-4,10-dien-2-yl)-propoxy]-tert-butyl-dimethyl-silane
CAS No.:123488-86-8
Molecular Formula:C₂₉H₄₈O₂SSi
Molecular Weight:488.85
Hs Code.:

Synonyms:[(R)-1-((4E,10Z)-(2R,6R,8S,9S)-9-Benzyloxy-6,8,10-trimethyl-thiacycloundeca-4,10-dien-2-yl)-propoxy]-tert-butyl-dimethyl-silane

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Chemical Property of [(R)-1-((4E,10Z)-(2R,6R,8S,9S)-9-Benzyloxy-6,8,10-trimethyl-thiacycloundeca-4,10-dien-2-yl)-propoxy]-tert-butyl-dimethyl-silane

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Technology Process of [(R)-1-((4E,10Z)-(2R,6R,8S,9S)-9-Benzyloxy-6,8,10-trimethyl-thiacycloundeca-4,10-dien-2-yl)-propoxy]-tert-butyl-dimethyl-silane

There total 7 articles about [(R)-1-((4E,10Z)-(2R,6R,8S,9S)-9-Benzyloxy-6,8,10-trimethyl-thiacycloundeca-4,10-dien-2-yl)-propoxy]-tert-butyl-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: 9.0%

: {(E)-(3R,4S,5S,7R,11R)-4-Benzyloxy-11-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-propyl]-3,5,7-trimethyl-1-oxo-1λ⁴-thia-cycloundec-8-en-2-yl}-diphenyl-phosphane

: 123488-86-8
[(R)-1-((4E,10Z)-(2R,6R,8S,9S)-9-Benzyloxy-6,8,10-trimethyl-thiacycloundeca-4,10-dien-2-yl)-propoxy]-tert-butyl-dimethyl-silane

: 110314-29-9,123538-65-8,123538-66-9
{(R)-1-[(E)-(2R,6R,8S,9S,10R)-9-Benzyloxy-11-(diphenyl-phosphinoyl)-6,8,10-trimethyl-thiacycloundec-4-en-2-yl]-propoxy}-tert-butyl-dimethyl-silane

Guidance literature:: With iodine; In tetrahydrofuran; dichloromethane; at 0 ℃; for 3h; Yields of byproduct given;
DOI:10.1021/ja00204a016

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 123488-86-8
[(R)-1-((4E,10Z)-(2R,6R,8S,9S)-9-Benzyloxy-6,8,10-trimethyl-thiacycloundeca-4,10-dien-2-yl)-propoxy]-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 4 steps

1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

2: 99 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 1.) -78 deg C, 3 h, 2.) -40 h, 1 h

3: 1.) n-BuLi, 1,10-phenanthroline / 1.) THF, -78 deg C, 1 h, 2.) 15 min

4: 9 percent / iodine / tetrahydrofuran; CH₂Cl₂ / 3 h / 0 °C

With 2,6-dimethylpyridine; n-butyllithium; 1,10-Phenanthroline; iodine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja00204a016

Reference yield:

: 110314-26-6,123538-63-6
1-((E)-(2R,6R,8S,9S,10R)-9-Benzyloxy-6,8,10-trimethyl-thiacycloundec-4-en-2-yl)-propan-1-one

: 123488-86-8
[(R)-1-((4E,10Z)-(2R,6R,8S,9S)-9-Benzyloxy-6,8,10-trimethyl-thiacycloundeca-4,10-dien-2-yl)-propoxy]-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 5 steps

1: 94.2 percent / LiHBEt₃ / tetrahydrofuran / 1.) -78 deg C, 2 h, 2.) room temp., 0.5 h

2: 99 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

3: 99 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 1.) -78 deg C, 3 h, 2.) -40 h, 1 h

4: 1.) n-BuLi, 1,10-phenanthroline / 1.) THF, -78 deg C, 1 h, 2.) 15 min

5: 9 percent / iodine / tetrahydrofuran; CH₂Cl₂ / 3 h / 0 °C

With 2,6-dimethylpyridine; n-butyllithium; 1,10-Phenanthroline; iodine; lithium triethylborohydride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja00204a016