(6E,10E,12E)(2R,4R,5R,13R)-9-(tert-butyldimethyl-silanyloxy)-1-(3,4-dimethoxy-benzyloxy)-5-hydroxy-13-iodo-2,4,7-trimethyl-trideca-6,10,12-trien-3-one

Base Information

Chemical Name:(6E,10E,12E)(2R,4R,5R,13R)-9-(tert-butyldimethyl-silanyloxy)-1-(3,4-dimethoxy-benzyloxy)-5-hydroxy-13-iodo-2,4,7-trimethyl-trideca-6,10,12-trien-3-one
CAS No.:627101-48-8
Molecular Formula:C₃₁H₄₉IO₆Si
Molecular Weight:672.716
Hs Code.:

(6E,10E,12E)(2R,4R,5R,13R)-9-(tert-butyldimethyl-silanyloxy)-1-(3,4-dimethoxy-benzyloxy)-5-hydroxy-13-iodo-2,4,7-trimethyl-trideca-6,10,12-trien-3-one

Synonyms:(6E,10E,12E)(2R,4R,5R,13R)-9-(tert-butyldimethyl-silanyloxy)-1-(3,4-dimethoxy-benzyloxy)-5-hydroxy-13-iodo-2,4,7-trimethyl-trideca-6,10,12-trien-3-one

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Chemical Property of (6E,10E,12E)(2R,4R,5R,13R)-9-(tert-butyldimethyl-silanyloxy)-1-(3,4-dimethoxy-benzyloxy)-5-hydroxy-13-iodo-2,4,7-trimethyl-trideca-6,10,12-trien-3-one

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Technology Process of (6E,10E,12E)(2R,4R,5R,13R)-9-(tert-butyldimethyl-silanyloxy)-1-(3,4-dimethoxy-benzyloxy)-5-hydroxy-13-iodo-2,4,7-trimethyl-trideca-6,10,12-trien-3-one

There total 9 articles about (6E,10E,12E)(2R,4R,5R,13R)-9-(tert-butyldimethyl-silanyloxy)-1-(3,4-dimethoxy-benzyloxy)-5-hydroxy-13-iodo-2,4,7-trimethyl-trideca-6,10,12-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:

: 627101-46-6
(R)-1-(3,4-Dimethoxy-benzyloxy)-2-methyl-pentan-3-one

: 627101-45-5
(2E,5S,6E,8E)-5-(tert-butyldimethylsilyloxy)-9-iodo-3-methyl-2,6,8-trienal

: (6E,10E,12E)-(2R,9R)-9-(tert-Butyl-dimethyl-silanyloxy)-1-(3,4-dimethoxy-benzyloxy)-5-hydroxy-13-iodo-2,4,7-trimethyl-trideca-6,10,12-trien-3-one

: 627101-48-8
(6E,10E,12E)(2R,4R,5R,13R)-9-(tert-butyldimethyl-silanyloxy)-1-(3,4-dimethoxy-benzyloxy)-5-hydroxy-13-iodo-2,4,7-trimethyl-trideca-6,10,12-trien-3-one

Guidance literature:: (R)-1-(3,4-Dimethoxy-benzyloxy)-2-methyl-pentan-3-one; With dicyclohexylboron chloride; triethylamine; In diethyl ether; at -20 ℃;

(2E,5S,6E,8E)-5-(tert-butyldimethylsilyloxy)-9-iodo-3-methyl-2,6,8-trienal; In diethyl ether; at -78 - -30 ℃; Title compound not separated from byproducts;
DOI:10.1021/ol0357853

Reference yield:

: 76927-59-8
(E)-((1-methoxy-3-methylbuta-1,3-dien-1-yl)oxy)trimethylsilane

: 627101-48-8
(6E,10E,12E)(2R,4R,5R,13R)-9-(tert-butyldimethyl-silanyloxy)-1-(3,4-dimethoxy-benzyloxy)-5-hydroxy-13-iodo-2,4,7-trimethyl-trideca-6,10,12-trien-3-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: 52 percent / titanium tetraisopropoxide; (R)-BINOL; molecular sieves 4 Angstroem / tetrahydrofuran / 14 h / -20 °C

2.1: imidazole / CH₂Cl₂

3.1: DIBAL / CH₂Cl₂ / -78 °C

4.1: MnO₂ / CH₂Cl₂

5.1: c-Hex₂BCl; Et₃N / diethyl ether / -20 °C

5.2: diethyl ether / -78 - -30 °C

With 1H-imidazole; titanium(IV) isopropylate; manganese(IV) oxide; 4 A molecular sieve; dicyclohexylboron chloride; (R)-1,1'-Bi-2-naphthol; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; 1.1: Mukaiyama aldol reaction;
DOI:10.1021/ol0357853

Reference yield:

: 905589-59-5
(3,4-dimethoxoxyphenyl)methyl 2,2,2-trichloroacetimidate

: 627101-48-8
(6E,10E,12E)(2R,4R,5R,13R)-9-(tert-butyldimethyl-silanyloxy)-1-(3,4-dimethoxy-benzyloxy)-5-hydroxy-13-iodo-2,4,7-trimethyl-trideca-6,10,12-trien-3-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: PPTS / CH₂Cl₂

2.1: i-PrMgCl / tetrahydrofuran / -20 °C

3.1: tetrahydrofuran / 0 °C

4.1: c-Hex₂BCl; Et₃N / diethyl ether / -20 °C

4.2: diethyl ether / -78 - -30 °C

With dicyclohexylboron chloride; isopropylmagnesium chloride; pyridinium p-toluenesulfonate; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/ol0357853