(5R,6S)-6-[(3Z,8Z)-(2S,5S,6S,7S,11S,12R,13R,14S,15S)-2,12-Bis-(tert-butyl-dimethyl-silanyloxy)-14-(4-methoxy-benzyloxy)-6-methoxymethoxy-5,7,9,11,13,15-hexamethyl-nonadeca-3,8-dienyl]-5-methyl-tetrahydro-pyran-2-one

Base Information

Chemical Name:(5R,6S)-6-[(3Z,8Z)-(2S,5S,6S,7S,11S,12R,13R,14S,15S)-2,12-Bis-(tert-butyl-dimethyl-silanyloxy)-14-(4-methoxy-benzyloxy)-6-methoxymethoxy-5,7,9,11,13,15-hexamethyl-nonadeca-3,8-dienyl]-5-methyl-tetrahydro-pyran-2-one
CAS No.:870075-21-1
Molecular Formula:C₅₃H₉₆O₈Si₂
Molecular Weight:917.511
Hs Code.:

(5R,6S)-6-[(3Z,8Z)-(2S,5S,6S,7S,11S,12R,13R,14S,15S)-2,12-Bis-(tert-butyl-dimethyl-silanyloxy)-14-(4-methoxy-benzyloxy)-6-methoxymethoxy-5,7,9,11,13,15-hexamethyl-nonadeca-3,8-dienyl]-5-methyl-tetrahydro-pyran-2-one

Synonyms:(5R,6S)-6-[(3Z,8Z)-(2S,5S,6S,7S,11S,12R,13R,14S,15S)-2,12-Bis-(tert-butyl-dimethyl-silanyloxy)-14-(4-methoxy-benzyloxy)-6-methoxymethoxy-5,7,9,11,13,15-hexamethyl-nonadeca-3,8-dienyl]-5-methyl-tetrahydro-pyran-2-one

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Chemical Property of (5R,6S)-6-[(3Z,8Z)-(2S,5S,6S,7S,11S,12R,13R,14S,15S)-2,12-Bis-(tert-butyl-dimethyl-silanyloxy)-14-(4-methoxy-benzyloxy)-6-methoxymethoxy-5,7,9,11,13,15-hexamethyl-nonadeca-3,8-dienyl]-5-methyl-tetrahydro-pyran-2-one

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Technology Process of (5R,6S)-6-[(3Z,8Z)-(2S,5S,6S,7S,11S,12R,13R,14S,15S)-2,12-Bis-(tert-butyl-dimethyl-silanyloxy)-14-(4-methoxy-benzyloxy)-6-methoxymethoxy-5,7,9,11,13,15-hexamethyl-nonadeca-3,8-dienyl]-5-methyl-tetrahydro-pyran-2-one

There total 9 articles about (5R,6S)-6-[(3Z,8Z)-(2S,5S,6S,7S,11S,12R,13R,14S,15S)-2,12-Bis-(tert-butyl-dimethyl-silanyloxy)-14-(4-methoxy-benzyloxy)-6-methoxymethoxy-5,7,9,11,13,15-hexamethyl-nonadeca-3,8-dienyl]-5-methyl-tetrahydro-pyran-2-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: 45.0%

: 853055-22-8
(S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-((2S,3R)-3-methyl-6-oxo-tetrahydro-pyran-2-yl)-propionaldehyde

: [(Z)-(2R,3R,4S,8S,9R,10R,11S,12S)-9-(tert-Butyl-dimethyl-silanyloxy)-11-(4-methoxy-benzyloxy)-3-methoxymethoxy-2,4,6,8,10,12-hexamethyl-hexadec-5-enyl]-triphenyl-phosphonium; iodide

: 870075-21-1
(5R,6S)-6-[(3Z,8Z)-(2S,5S,6S,7S,11S,12R,13R,14S,15S)-2,12-Bis-(tert-butyl-dimethyl-silanyloxy)-14-(4-methoxy-benzyloxy)-6-methoxymethoxy-5,7,9,11,13,15-hexamethyl-nonadeca-3,8-dienyl]-5-methyl-tetrahydro-pyran-2-one

Guidance literature:: With methyllithium;
DOI:10.1021/ol052070m

Reference yield:

: 837383-29-6
(5R,6S)-6-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-propyl]-5-methyl-5,6-dihydro-pyran-2-one

: 870075-21-1
(5R,6S)-6-[(3Z,8Z)-(2S,5S,6S,7S,11S,12R,13R,14S,15S)-2,12-Bis-(tert-butyl-dimethyl-silanyloxy)-14-(4-methoxy-benzyloxy)-6-methoxymethoxy-5,7,9,11,13,15-hexamethyl-nonadeca-3,8-dienyl]-5-methyl-tetrahydro-pyran-2-one

Guidance literature:: Multi-step reaction with 3 steps

1: 100 percent / H₂ / Pd(OH)2 / ethyl acetate / 2 h

2: 95 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 2.5 h / 0 °C

3: 45 percent / MeLi

With methyllithium; hydrogen; sodium hydrogencarbonate; Dess-Martin periodane; palladium dihydroxide; In dichloromethane; ethyl acetate; 2: Dess-Martin oxidation / 3: Wittig reaction;
DOI:10.1021/ol052070m

Reference yield:

: 398518-64-4
(2S,3R,4R,5S,6S,Z)-3-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-2,4,6-trimethyldeca-7,9-dien-1-ol

: 870075-21-1
(5R,6S)-6-[(3Z,8Z)-(2S,5S,6S,7S,11S,12R,13R,14S,15S)-2,12-Bis-(tert-butyl-dimethyl-silanyloxy)-14-(4-methoxy-benzyloxy)-6-methoxymethoxy-5,7,9,11,13,15-hexamethyl-nonadeca-3,8-dienyl]-5-methyl-tetrahydro-pyran-2-one

Guidance literature:: Multi-step reaction with 7 steps

1: 95 percent / H₂ / PtO₂ / ethyl acetate / 1 h

2: 95 percent / PPh₃; imidazole; I₂ / benzene; diethyl ether / 1 h / 20 °C

3: 82 percent / Cs₂CO₃ / Pd(dppf)2

4: 90 percent / aq. HCl

5: I₂; PPh₃; imidazole

6: DIPEA / 100 °C

7: 45 percent / MeLi

With 1H-imidazole; hydrogenchloride; methyllithium; hydrogen; iodine; caesium carbonate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; platinum(IV) oxide; bis[1,2-bis(diphenylphosphino)ferrocene]-palladium⁽⁰⁾; In diethyl ether; ethyl acetate; benzene; 3: Suzuki coupling / 7: Wittig reaction;
DOI:10.1021/ol052070m