(5S,2E)-3-(4’-benzenesulfoxyphenyl)ethynyl-5-(tert-butyldimethyl)silyloxy-1,7-di(4’-(benzenesulfoxy))phenylheptanone

Base Information

Chemical Name:(5S,2E)-3-(4’-benzenesulfoxyphenyl)ethynyl-5-(tert-butyldimethyl)silyloxy-1,7-di(4’-(benzenesulfoxy))phenylheptanone
CAS No.:1429416-53-4
Molecular Formula:C₅₁H₅₄O₁₁S₃Si
Molecular Weight:967.267
Hs Code.:

Synonyms:(5S,2E)-3-(4’-benzenesulfoxyphenyl)ethynyl-5-(tert-butyldimethyl)silyloxy-1,7-di(4’-(benzenesulfoxy))phenylheptanone

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (5S,2E)-3-(4’-benzenesulfoxyphenyl)ethynyl-5-(tert-butyldimethyl)silyloxy-1,7-di(4’-(benzenesulfoxy))phenylheptanone

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Technology Process of (5S,2E)-3-(4’-benzenesulfoxyphenyl)ethynyl-5-(tert-butyldimethyl)silyloxy-1,7-di(4’-(benzenesulfoxy))phenylheptanone

There total 16 articles about (5S,2E)-3-(4’-benzenesulfoxyphenyl)ethynyl-5-(tert-butyldimethyl)silyloxy-1,7-di(4’-(benzenesulfoxy))phenylheptanone 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: 90.0%

: 1429416-52-3
(5S,2E)-5-(tert-butyldimethyl)silyloxy-1,7-di(4’-(benzenesulfoxy))phenylhept-2-en-1-one

: 1429428-46-5
C₁₉H₁₈BNO₇S

: 1429416-53-4
(5S,2E)-3-(4’-benzenesulfoxyphenyl)ethynyl-5-(tert-butyldimethyl)silyloxy-1,7-di(4’-(benzenesulfoxy))phenylheptanone

Guidance literature:: With chloro(1,5-cyclooctadiene)rhodium(I) dimer; sodium hydroxide; lithium hydroxide; In 1,4-dioxane; aq. phosphate buffer; water; for 3h; pH=7; Reflux;
DOI:10.1021/ol400736w

Reference yield:

: 31770-76-0
3-(4-hydroxyphenyl)propionic acid benzyl ester

: 1429416-53-4
(5S,2E)-3-(4’-benzenesulfoxyphenyl)ethynyl-5-(tert-butyldimethyl)silyloxy-1,7-di(4’-(benzenesulfoxy))phenylheptanone

Guidance literature:: Multi-step reaction with 8 steps

1: triethylamine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere

2: diisobutylaluminium hydride / dichloromethane; hexane / 6 h / -78 °C / Inert atmosphere

3: toluene-4-sulfonic acid / dichloromethane / 20 h / Inert atmosphere

4: 1H-imidazole; dmap / dichloromethane / 40 h / Inert atmosphere

5: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran / 0.75 h / Inert atmosphere

6: sodium periodate / tetrahydrofuran; water / 3 h

7: toluene / 20 h / Reflux

8: chloro(1,5-cyclooctadiene)rhodium(I) dimer; lithium hydroxide; sodium hydroxide / water; 1,4-dioxane; aq. phosphate buffer / 3 h / pH 7 / Reflux

With 1H-imidazole; dmap; sodium periodate; osmium(VIII) oxide; chloro(1,5-cyclooctadiene)rhodium(I) dimer; diisobutylaluminium hydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; sodium hydroxide; lithium hydroxide; In tetrahydrofuran; 1,4-dioxane; aq. phosphate buffer; hexane; dichloromethane; water; toluene;
DOI:10.1021/ol400736w

Reference yield:

: 98-09-9
benzenesulfonyl chloride

: 1429416-53-4
(5S,2E)-3-(4’-benzenesulfoxyphenyl)ethynyl-5-(tert-butyldimethyl)silyloxy-1,7-di(4’-(benzenesulfoxy))phenylheptanone

Guidance literature:: Multi-step reaction with 4 steps

1.1: triethylamine / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere

2.1: chloroform / 18 h

2.2: 3 h

3.1: toluene / 20 h / Reflux

4.1: chloro(1,5-cyclooctadiene)rhodium(I) dimer; lithium hydroxide; sodium hydroxide / water; 1,4-dioxane; aq. phosphate buffer / 3 h / pH 7 / Reflux

With chloro(1,5-cyclooctadiene)rhodium(I) dimer; triethylamine; sodium hydroxide; lithium hydroxide; In 1,4-dioxane; aq. phosphate buffer; dichloromethane; chloroform; water; toluene;
DOI:10.1021/ol400736w