(6R,8R,9S,10R,13S,15S,16E,20S,22E)-6,9,10-tris(tert-butyldimethylsiloxy)-13-hydroxy-2,2,3,3,8,15,16,20,27,27-decamethyl-18-methylene-26,26-diphenyl-4,25-dioxa-3,26-disilaoctacosa-16,22-dien-11-one

Base Information

Chemical Name:(6R,8R,9S,10R,13S,15S,16E,20S,22E)-6,9,10-tris(tert-butyldimethylsiloxy)-13-hydroxy-2,2,3,3,8,15,16,20,27,27-decamethyl-18-methylene-26,26-diphenyl-4,25-dioxa-3,26-disilaoctacosa-16,22-dien-11-one
CAS No.:1315317-47-5
Molecular Formula:C₆₅H₁₁₈O₇Si₅
Molecular Weight:1152.08
Hs Code.:

(6R,8R,9S,10R,13S,15S,16E,20S,22E)-6,9,10-tris(tert-butyldimethylsiloxy)-13-hydroxy-2,2,3,3,8,15,16,20,27,27-decamethyl-18-methylene-26,26-diphenyl-4,25-dioxa-3,26-disilaoctacosa-16,22-dien-11-one

Synonyms:(6R,8R,9S,10R,13S,15S,16E,20S,22E)-6,9,10-tris(tert-butyldimethylsiloxy)-13-hydroxy-2,2,3,3,8,15,16,20,27,27-decamethyl-18-methylene-26,26-diphenyl-4,25-dioxa-3,26-disilaoctacosa-16,22-dien-11-one

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Chemical Property of (6R,8R,9S,10R,13S,15S,16E,20S,22E)-6,9,10-tris(tert-butyldimethylsiloxy)-13-hydroxy-2,2,3,3,8,15,16,20,27,27-decamethyl-18-methylene-26,26-diphenyl-4,25-dioxa-3,26-disilaoctacosa-16,22-dien-11-one

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Technology Process of (6R,8R,9S,10R,13S,15S,16E,20S,22E)-6,9,10-tris(tert-butyldimethylsiloxy)-13-hydroxy-2,2,3,3,8,15,16,20,27,27-decamethyl-18-methylene-26,26-diphenyl-4,25-dioxa-3,26-disilaoctacosa-16,22-dien-11-one

There total 38 articles about (6R,8R,9S,10R,13S,15S,16E,20S,22E)-6,9,10-tris(tert-butyldimethylsiloxy)-13-hydroxy-2,2,3,3,8,15,16,20,27,27-decamethyl-18-methylene-26,26-diphenyl-4,25-dioxa-3,26-disilaoctacosa-16,22-dien-11-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:

: 1315317-36-2
(3S,4E,8S,10E)-12-(tert-butyldiphenylsilyloxy)-3,4,8-trimethyl-6-methylenedodeca-4,10-dienal

: 1315317-37-3
(3R,4S,5R,7R)-3,4,7,8-tetrakis(tert-butyldimethylsiloxy)-5-methyloctan-2-one

: 1315317-47-5
(6R,8R,9S,10R,13S,15S,16E,20S,22E)-6,9,10-tris(tert-butyldimethylsiloxy)-13-hydroxy-2,2,3,3,8,15,16,20,27,27-decamethyl-18-methylene-26,26-diphenyl-4,25-dioxa-3,26-disilaoctacosa-16,22-dien-11-one

: 1315317-48-6
(6R,8R,9S,10R,13R,15S,16E,20S,22E)-6,9,10-tris(tert-butyldimethylsiloxy)-13-hydroxy-2,2,3,3,8,15,16,20,27,27-decamethyl-18-methylene-26,26-diphenyl-4,25-dioxa-3,26-disilaoctacosa-16,22-dien-11-one

Guidance literature:: (3R,4S,5R,7R)-3,4,7,8-tetrakis(tert-butyldimethylsiloxy)-5-methyloctan-2-one; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 - 20 ℃; for 2h; Inert atmosphere;

(3S,4E,8S,10E)-12-(tert-butyldiphenylsilyloxy)-3,4,8-trimethyl-6-methylenedodeca-4,10-dienal; In tetrahydrofuran; at -10 ℃; for 0.0833333h; Inert atmosphere;

With ammonium chloride; In tetrahydrofuran; water; optical yield given as %de; diastereoselective reaction; Inert atmosphere; Saturated solution;
DOI:10.1021/ol201547q

Reference yield:

: 1033074-47-3
(S)-1-((5,5-dibromo-3-methylpent-4-enyloxy)methyl)-4-methoxybenzene

: 1315317-47-5
(6R,8R,9S,10R,13S,15S,16E,20S,22E)-6,9,10-tris(tert-butyldimethylsiloxy)-13-hydroxy-2,2,3,3,8,15,16,20,27,27-decamethyl-18-methylene-26,26-diphenyl-4,25-dioxa-3,26-disilaoctacosa-16,22-dien-11-one

: 1315317-48-6
(6R,8R,9S,10R,13R,15S,16E,20S,22E)-6,9,10-tris(tert-butyldimethylsiloxy)-13-hydroxy-2,2,3,3,8,15,16,20,27,27-decamethyl-18-methylene-26,26-diphenyl-4,25-dioxa-3,26-disilaoctacosa-16,22-dien-11-one

Guidance literature:: Multi-step reaction with 10 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 - 0 °C / Inert atmosphere

2.2: 0 °C / Inert atmosphere

2.3: 0 °C / Inert atmosphere; Saturated solution

3.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 3 h / 20 °C / Inert atmosphere; Molecular sieve

4.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h / 0 - 20 °C / aq. phosphate buffer

5.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

6.1: copper(l) cyanide / diethyl ether / 1 h / -78 °C / Inert atmosphere

7.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / 0 °C / Inert atmosphere

7.2: 24 h / 0 - 20 °C / Inert atmosphere

8.1: pyridinium p-toluenesulfonate / methanol; dichloromethane / 2 h / 0 °C / Inert atmosphere

9.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 2 h / 0 - 20 °C / Inert atmosphere

10.1: lithium hexamethyldisilazane / tetrahydrofuran / -78 °C / Inert atmosphere

With n-butyllithium; tetrapropylammonium perruthennate; copper(l) cyanide; pyridinium p-toluenesulfonate; 4-methylmorpholine N-oxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; 7.1: Wittig reaction / 10.1: Aldol condensation;
DOI:10.1021/ol201547q

Reference yield:

: 1315317-41-9
(7S,12S,E)-3,3-diethyl-7,12,19,19-tetramethyl-18,18-diphenyl-4,17-dioxa-3,18-disilaicos-14-en-8-yn-10-one

: 1315317-47-5
(6R,8R,9S,10R,13S,15S,16E,20S,22E)-6,9,10-tris(tert-butyldimethylsiloxy)-13-hydroxy-2,2,3,3,8,15,16,20,27,27-decamethyl-18-methylene-26,26-diphenyl-4,25-dioxa-3,26-disilaoctacosa-16,22-dien-11-one

: 1315317-48-6
(6R,8R,9S,10R,13R,15S,16E,20S,22E)-6,9,10-tris(tert-butyldimethylsiloxy)-13-hydroxy-2,2,3,3,8,15,16,20,27,27-decamethyl-18-methylene-26,26-diphenyl-4,25-dioxa-3,26-disilaoctacosa-16,22-dien-11-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: copper(l) cyanide / diethyl ether / 1 h / -78 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / 0 °C / Inert atmosphere

2.2: 24 h / 0 - 20 °C / Inert atmosphere

3.1: pyridinium p-toluenesulfonate / methanol; dichloromethane / 2 h / 0 °C / Inert atmosphere

4.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 2 h / 0 - 20 °C / Inert atmosphere

5.1: lithium hexamethyldisilazane / tetrahydrofuran / -78 °C / Inert atmosphere

With n-butyllithium; copper(l) cyanide; pyridinium p-toluenesulfonate; lithium hexamethyldisilazane; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; 2.1: Wittig reaction / 5.1: Aldol condensation;
DOI:10.1021/ol201547q