(2R,5S,6R,7S,9S,10E,13R,14E,16E)-13-(tert-butyldimethylsilyloxy)-1-(3,4-dimethoxybenzyloxy)-17-bromo-5-hydroxy-9-methoxy-7-triethylsilyloxy-2,6,11-trimethyl-heptadeca-10,14,16-trien-3-one

Base Information

Chemical Name:(2R,5S,6R,7S,9S,10E,13R,14E,16E)-13-(tert-butyldimethylsilyloxy)-1-(3,4-dimethoxybenzyloxy)-17-bromo-5-hydroxy-9-methoxy-7-triethylsilyloxy-2,6,11-trimethyl-heptadeca-10,14,16-trien-3-one
CAS No.:889454-40-4
Molecular Formula:C₄₂H₇₃BrO₈Si₂
Molecular Weight:842.112
Hs Code.:

(2R,5S,6R,7S,9S,10E,13R,14E,16E)-13-(tert-butyldimethylsilyloxy)-1-(3,4-dimethoxybenzyloxy)-17-bromo-5-hydroxy-9-methoxy-7-triethylsilyloxy-2,6,11-trimethyl-heptadeca-10,14,16-trien-3-one

Synonyms:(2R,5S,6R,7S,9S,10E,13R,14E,16E)-13-(tert-butyldimethylsilyloxy)-1-(3,4-dimethoxybenzyloxy)-17-bromo-5-hydroxy-9-methoxy-7-triethylsilyloxy-2,6,11-trimethyl-heptadeca-10,14,16-trien-3-one

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Chemical Property of (2R,5S,6R,7S,9S,10E,13R,14E,16E)-13-(tert-butyldimethylsilyloxy)-1-(3,4-dimethoxybenzyloxy)-17-bromo-5-hydroxy-9-methoxy-7-triethylsilyloxy-2,6,11-trimethyl-heptadeca-10,14,16-trien-3-one

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Technology Process of (2R,5S,6R,7S,9S,10E,13R,14E,16E)-13-(tert-butyldimethylsilyloxy)-1-(3,4-dimethoxybenzyloxy)-17-bromo-5-hydroxy-9-methoxy-7-triethylsilyloxy-2,6,11-trimethyl-heptadeca-10,14,16-trien-3-one

There total 9 articles about (2R,5S,6R,7S,9S,10E,13R,14E,16E)-13-(tert-butyldimethylsilyloxy)-1-(3,4-dimethoxybenzyloxy)-17-bromo-5-hydroxy-9-methoxy-7-triethylsilyloxy-2,6,11-trimethyl-heptadeca-10,14,16-trien-3-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:

: 889454-41-5
(R)-3-(3,4-dimethoxybenzyloxy)-2-methylbutan-3-one

: 889454-43-7
(6E,10E,12E)-(2S,3S,5S,9R)-13-Bromo-9-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-2,7-dimethyl-3-triethylsilanyloxy-trideca-6,10,12-trienal

: 889454-40-4
(2R,5S,6R,7S,9S,10E,13R,14E,16E)-13-(tert-butyldimethylsilyloxy)-1-(3,4-dimethoxybenzyloxy)-17-bromo-5-hydroxy-9-methoxy-7-triethylsilyloxy-2,6,11-trimethyl-heptadeca-10,14,16-trien-3-one

Guidance literature:: With dicyclohexylboron chloride; triethylamine; In diethyl ether; at -78 - -27 ℃; for 17h;
DOI:10.1021/ol060609q

Reference yield:

: 889454-41-5
(R)-3-(3,4-dimethoxybenzyloxy)-2-methylbutan-3-one

: 889454-40-4
(2R,5S,6R,7S,9S,10E,13R,14E,16E)-13-(tert-butyldimethylsilyloxy)-1-(3,4-dimethoxybenzyloxy)-17-bromo-5-hydroxy-9-methoxy-7-triethylsilyloxy-2,6,11-trimethyl-heptadeca-10,14,16-trien-3-one

Guidance literature:: Multi-step reaction with 8 steps

1: 80 percent / samarium diiodide / tetrahydrofuran / 1 h / -10 °C

2: 90 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

3: 87 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C

4: 96 percent / Proton Sponge / CH₂Cl₂ / 1 h / 20 °C

5: 77 percent / DDQ / CH₂Cl₂; H₂O / 0.17 h / pH 7 / Heating

6: Dess-Martin periodinane; pyridine / CH₂Cl₂ / 1 h / 20 °C

7: 120 mg / triethylamine; dicyclohexylboron chloride / diethyl ether / 17 h / -78 - -27 °C

With pyridine; 2,6-dimethylpyridine; samarium diiodide; Proton Sponge; dicyclohexylboron chloride; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; dichloromethane; water;
DOI:10.1021/ol060609q

Reference yield:

: 889454-46-0
(2R,3S,5S,6E,9R,10E,12E)-(2R,3S,5R,9R)-9-(tert-butyldimethylsilyloxy)-13-bromo-5-methoxy-2,7-dimethyl-3-triethylsilyloxy-trideca-6,10,12-trienol

: 889454-40-4
(2R,5S,6R,7S,9S,10E,13R,14E,16E)-13-(tert-butyldimethylsilyloxy)-1-(3,4-dimethoxybenzyloxy)-17-bromo-5-hydroxy-9-methoxy-7-triethylsilyloxy-2,6,11-trimethyl-heptadeca-10,14,16-trien-3-one

Guidance literature:: Multi-step reaction with 2 steps

1: Dess-Martin periodinane; pyridine / CH₂Cl₂ / 1 h / 20 °C

2: 120 mg / triethylamine; dicyclohexylboron chloride / diethyl ether / 17 h / -78 - -27 °C

With pyridine; dicyclohexylboron chloride; Dess-Martin periodane; triethylamine; In diethyl ether; dichloromethane;
DOI:10.1021/ol060609q