(Z)-(2S,8S,9R,11S,13S)-11,13-Bis-(tert-butyl-dimethyl-silanyloxy)-14-{(2R,6R)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-yl}-2-methoxy-1,9-bis-(4-methoxy-benzyloxy)-8-methyl-tetradec-6-en-5-one

Base Information

Chemical Name:(Z)-(2S,8S,9R,11S,13S)-11,13-Bis-(tert-butyl-dimethyl-silanyloxy)-14-{(2R,6R)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-yl}-2-methoxy-1,9-bis-(4-methoxy-benzyloxy)-8-methyl-tetradec-6-en-5-one
CAS No.:876144-59-1
Molecular Formula:C₆₇H₁₀₄O₁₀Si₃
Molecular Weight:1153.81
Hs Code.:

(Z)-(2S,8S,9R,11S,13S)-11,13-Bis-(tert-butyl-dimethyl-silanyloxy)-14-{(2R,6R)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-yl}-2-methoxy-1,9-bis-(4-methoxy-benzyloxy)-8-methyl-tetradec-6-en-5-one

Synonyms:(Z)-(2S,8S,9R,11S,13S)-11,13-Bis-(tert-butyl-dimethyl-silanyloxy)-14-{(2R,6R)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-yl}-2-methoxy-1,9-bis-(4-methoxy-benzyloxy)-8-methyl-tetradec-6-en-5-one

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Chemical Property of (Z)-(2S,8S,9R,11S,13S)-11,13-Bis-(tert-butyl-dimethyl-silanyloxy)-14-{(2R,6R)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-yl}-2-methoxy-1,9-bis-(4-methoxy-benzyloxy)-8-methyl-tetradec-6-en-5-one

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Technology Process of (Z)-(2S,8S,9R,11S,13S)-11,13-Bis-(tert-butyl-dimethyl-silanyloxy)-14-{(2R,6R)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-yl}-2-methoxy-1,9-bis-(4-methoxy-benzyloxy)-8-methyl-tetradec-6-en-5-one

There total 22 articles about (Z)-(2S,8S,9R,11S,13S)-11,13-Bis-(tert-butyl-dimethyl-silanyloxy)-14-{(2R,6R)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-yl}-2-methoxy-1,9-bis-(4-methoxy-benzyloxy)-8-methyl-tetradec-6-en-5-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: 86.0%

: 876144-71-7
(Z)-(2S,8S,9R,11S,13S)-11,13-Bis-(tert-butyl-dimethyl-silanyloxy)-14-{(2R,6R)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-yl}-2-methoxy-1,9-bis-(4-methoxy-benzyloxy)-8-methyl-tetradec-6-en-5-ol

: 876144-59-1
(Z)-(2S,8S,9R,11S,13S)-11,13-Bis-(tert-butyl-dimethyl-silanyloxy)-14-{(2R,6R)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-yl}-2-methoxy-1,9-bis-(4-methoxy-benzyloxy)-8-methyl-tetradec-6-en-5-one

Guidance literature:: With phthalic acid dimethyl ester; sodium hydrogencarbonate; In dichloromethane;
DOI:10.1055/s-2005-918449

Reference yield:

: 876144-70-6
1-Methoxy-4-((S)-2-methoxy-hex-5-enyloxymethyl)-benzene

: 876144-59-1
(Z)-(2S,8S,9R,11S,13S)-11,13-Bis-(tert-butyl-dimethyl-silanyloxy)-14-{(2R,6R)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-yl}-2-methoxy-1,9-bis-(4-methoxy-benzyloxy)-8-methyl-tetradec-6-en-5-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: 89 percent / aq. OsO₄; NaIO₄ / tetrahydrofuran

2.1: n-BuLi / tetrahydrofuran / -20 °C

2.2: 93 percent / tetrahydrofuran / -20 °C

3.1: 97 percent / H₂; quinoline / Pd/CaCO₃/Pb / methanol

4.1: 86 percent / DMP; NaHCO₃ / CH₂Cl₂

With quinoline; sodium periodate; osmium(VIII) oxide; n-butyllithium; phthalic acid dimethyl ester; hydrogen; sodium hydrogencarbonate; Lindlar's catalyst; In tetrahydrofuran; methanol; dichloromethane; 3.1: Lindlar hydrogenation / 4.1: Dess-Martin oxidation;
DOI:10.1055/s-2005-918449

Reference yield:

: 876144-62-6
(2R,3R)-3-(4-Methoxy-benzyloxy)-2-methyl-hex-5-enal

: 876144-59-1
(Z)-(2S,8S,9R,11S,13S)-11,13-Bis-(tert-butyl-dimethyl-silanyloxy)-14-{(2R,6R)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-yl}-2-methoxy-1,9-bis-(4-methoxy-benzyloxy)-8-methyl-tetradec-6-en-5-one

Guidance literature:: Multi-step reaction with 9 steps

1.1: 98 percent / PPh₃ / CH₂Cl₂

2.1: O₂; CuCl / PdCl₂ / dimethylformamide; H₂O

3.1: (-)-Ipc₂BCl; Et₃N / diethyl ether

3.2: 79 percent / diethyl ether / -78 - -20 °C

4.1: 92 percent / Me₄NBH(OAc)3 / acetonitrile; acetic acid / -30 °C

5.1: 2,6-lutidine / CH₂Cl₂

6.1: n-BuLi / tetrahydrofuran / -30 °C

7.1: n-BuLi / tetrahydrofuran / -20 °C

7.2: 93 percent / tetrahydrofuran / -20 °C

8.1: 97 percent / H₂; quinoline / Pd/CaCO₃/Pb / methanol

9.1: 86 percent / DMP; NaHCO₃ / CH₂Cl₂

With 2,6-dimethylpyridine; quinoline; n-butyllithium; phthalic acid dimethyl ester; hydrogen; oxygen; sodium hydrogencarbonate; triethylamine; triphenylphosphine; (-)-diisopinocamphenylborane chloride; copper(l) chloride; tetramethylammonium triacetoxyborohydride; Lindlar's catalyst; palladium dichloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; acetonitrile; 1.1: Corey-Fuchs homologation / 2.1: Wacker oxidation / 8.1: Lindlar hydrogenation / 9.1: Dess-Martin oxidation;
DOI:10.1055/s-2005-918449