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

Base Information

Chemical Name:(5S,2E)-5-(tert-butyldimethyl)silyloxy-1,7-di(4’-(benzenesulfoxy))phenylhept-2-en-1-one
CAS No.:1429416-52-3
Molecular Formula:C₃₇H₄₂O₈S₂Si
Molecular Weight:706.953
Hs Code.:

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

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Chemical Property of (5S,2E)-5-(tert-butyldimethyl)silyloxy-1,7-di(4’-(benzenesulfoxy))phenylhept-2-en-1-one

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Technology Process of (5S,2E)-5-(tert-butyldimethyl)silyloxy-1,7-di(4’-(benzenesulfoxy))phenylhept-2-en-1-one

There total 11 articles about (5S,2E)-5-(tert-butyldimethyl)silyloxy-1,7-di(4’-(benzenesulfoxy))phenylhept-2-en-1-one 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: 91.0%

: 1429416-49-8
(S)-5-(4'-benzenesulfoxyphenyl)-3-(tertbutyldimethylsilyloxy)pentanal

: 1429416-51-2
triphenyl-(4-(benzenesulfoxy)benzoyl)-2’-methylenephosphorane

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

Guidance literature:: In toluene; for 20h; Reflux;
DOI:10.1021/ol400736w

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 7 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

With 1H-imidazole; dmap; sodium periodate; osmium(VIII) oxide; diisobutylaluminium hydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; water; toluene;
DOI:10.1021/ol400736w

Reference yield:

: benzyl 3-(4’-benzenesulfoxyphenyl)propionate

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

Guidance literature:: Multi-step reaction with 6 steps

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

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

3: 1H-imidazole; dmap / dichloromethane / 40 h / Inert atmosphere

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

5: sodium periodate / tetrahydrofuran; water / 3 h

6: toluene / 20 h / Reflux

With 1H-imidazole; dmap; sodium periodate; osmium(VIII) oxide; diisobutylaluminium hydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; In tetrahydrofuran; hexane; dichloromethane; water; toluene;
DOI:10.1021/ol400736w