(3R,5S,7S,11S)-11-(tert-butyldimethylsilanyloxy)-3-(tert-butyldiphenylsilanyloxy)-7-hydroxy-5-(4-methoxybenzyloxy)-8,8-dimethyl-9-methylenetetradec-13-enethioic acid S-tert-butyl ester

Base Information

Chemical Name:(3R,5S,7S,11S)-11-(tert-butyldimethylsilanyloxy)-3-(tert-butyldiphenylsilanyloxy)-7-hydroxy-5-(4-methoxybenzyloxy)-8,8-dimethyl-9-methylenetetradec-13-enethioic acid S-tert-butyl ester
CAS No.:910046-64-9
Molecular Formula:C₅₁H₇₈O₆SSi₂
Molecular Weight:875.414
Hs Code.:

(3R,5S,7S,11S)-11-(tert-butyldimethylsilanyloxy)-3-(tert-butyldiphenylsilanyloxy)-7-hydroxy-5-(4-methoxybenzyloxy)-8,8-dimethyl-9-methylenetetradec-13-enethioic acid S-tert-butyl ester

Synonyms:(3R,5S,7S,11S)-11-(tert-butyldimethylsilanyloxy)-3-(tert-butyldiphenylsilanyloxy)-7-hydroxy-5-(4-methoxybenzyloxy)-8,8-dimethyl-9-methylenetetradec-13-enethioic acid S-tert-butyl ester

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Chemical Property of (3R,5S,7S,11S)-11-(tert-butyldimethylsilanyloxy)-3-(tert-butyldiphenylsilanyloxy)-7-hydroxy-5-(4-methoxybenzyloxy)-8,8-dimethyl-9-methylenetetradec-13-enethioic acid S-tert-butyl ester

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Technology Process of (3R,5S,7S,11S)-11-(tert-butyldimethylsilanyloxy)-3-(tert-butyldiphenylsilanyloxy)-7-hydroxy-5-(4-methoxybenzyloxy)-8,8-dimethyl-9-methylenetetradec-13-enethioic acid S-tert-butyl ester

There total 5 articles about (3R,5S,7S,11S)-11-(tert-butyldimethylsilanyloxy)-3-(tert-butyldiphenylsilanyloxy)-7-hydroxy-5-(4-methoxybenzyloxy)-8,8-dimethyl-9-methylenetetradec-13-enethioic acid S-tert-butyl ester 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: 88.0%

: ((S)-1-allyl-4-methyl-3-tributylstannylmethyl-pent-3-enyloxy)tert-butyldimethylsilane

: 910046-62-7
(3R,5S)-3-(tert-butyldiphenylsilanyloxy)-5-(4-methoxybenzyloxy)oct-7-oxoheptanethioic acid S-tert-butyl ester

: 910046-64-9
(3R,5S,7S,11S)-11-(tert-butyldimethylsilanyloxy)-3-(tert-butyldiphenylsilanyloxy)-7-hydroxy-5-(4-methoxybenzyloxy)-8,8-dimethyl-9-methylenetetradec-13-enethioic acid S-tert-butyl ester

Guidance literature:: With dimethylaluminum chloride; In toluene; at -78 ℃; for 2h;
DOI:10.1021/ol061173h

Reference yield:

: 910046-60-5
(3R,5S)-3-hydroxy-5-(4-methoxybenzyloxy)oct-7-enethioic acid S-tert-butyl ester

: 910046-64-9
(3R,5S,7S,11S)-11-(tert-butyldimethylsilanyloxy)-3-(tert-butyldiphenylsilanyloxy)-7-hydroxy-5-(4-methoxybenzyloxy)-8,8-dimethyl-9-methylenetetradec-13-enethioic acid S-tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: imidazole / dimethylformamide / 24 h / 20 °C

2: OsO₄; H₂O; 4-methylmorpholine N-oxide / tetrahydrofuran; 2-methyl-propan-2-ol / 14 h / 20 °C

3: Pb(OAc)4 / benzene / 1 h / 20 °C

4: 88 percent / Me₂AlCl / toluene / 2 h / -78 °C

With 1H-imidazole; lead(IV) acetate; osmium(VIII) oxide; water; dimethylaluminum chloride; 4-methylmorpholine N-oxide; In tetrahydrofuran; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; benzene;
DOI:10.1021/ol061173h

Reference yield:

: 910046-76-3
(3R,5S)-3-(tert-butyldiphenylsilanyloxy)-5-(4-methoxybenzyloxy)oct-7-enethioic acid S-tert-butyl ester

: 910046-64-9
(3R,5S,7S,11S)-11-(tert-butyldimethylsilanyloxy)-3-(tert-butyldiphenylsilanyloxy)-7-hydroxy-5-(4-methoxybenzyloxy)-8,8-dimethyl-9-methylenetetradec-13-enethioic acid S-tert-butyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: OsO₄; H₂O; 4-methylmorpholine N-oxide / tetrahydrofuran; 2-methyl-propan-2-ol / 14 h / 20 °C

2: Pb(OAc)4 / benzene / 1 h / 20 °C

3: 88 percent / Me₂AlCl / toluene / 2 h / -78 °C

With lead(IV) acetate; osmium(VIII) oxide; water; dimethylaluminum chloride; 4-methylmorpholine N-oxide; In tetrahydrofuran; toluene; tert-butyl alcohol; benzene;
DOI:10.1021/ol061173h