(E)-(R)-5-{(2R,6R)-6-[(2E,6Z)-(R)-4,8-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-octa-2,6-dienyl]-4-methylene-tetrahydro-pyran-2-yl}-1-(3,4-dimethoxy-benzyloxy)-4-methyl-pent-4-en-2-ol

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Chemical Name:(E)-(R)-5-{(2R,6R)-6-[(2E,6Z)-(R)-4,8-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-octa-2,6-dienyl]-4-methylene-tetrahydro-pyran-2-yl}-1-(3,4-dimethoxy-benzyloxy)-4-methyl-pent-4-en-2-ol
CAS No.:405176-40-1
Molecular Formula:C₄₂H₇₂O₇Si₂
Molecular Weight:745.2
Hs Code.:

(E)-(R)-5-{(2R,6R)-6-[(2E,6Z)-(R)-4,8-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-octa-2,6-dienyl]-4-methylene-tetrahydro-pyran-2-yl}-1-(3,4-dimethoxy-benzyloxy)-4-methyl-pent-4-en-2-ol

Synonyms:(E)-(R)-5-{(2R,6R)-6-[(2E,6Z)-(R)-4,8-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-octa-2,6-dienyl]-4-methylene-tetrahydro-pyran-2-yl}-1-(3,4-dimethoxy-benzyloxy)-4-methyl-pent-4-en-2-ol

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Chemical Property of (E)-(R)-5-{(2R,6R)-6-[(2E,6Z)-(R)-4,8-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-octa-2,6-dienyl]-4-methylene-tetrahydro-pyran-2-yl}-1-(3,4-dimethoxy-benzyloxy)-4-methyl-pent-4-en-2-ol

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Technology Process of (E)-(R)-5-{(2R,6R)-6-[(2E,6Z)-(R)-4,8-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-octa-2,6-dienyl]-4-methylene-tetrahydro-pyran-2-yl}-1-(3,4-dimethoxy-benzyloxy)-4-methyl-pent-4-en-2-ol

There total 15 articles about (E)-(R)-5-{(2R,6R)-6-[(2E,6Z)-(R)-4,8-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-octa-2,6-dienyl]-4-methylene-tetrahydro-pyran-2-yl}-1-(3,4-dimethoxy-benzyloxy)-4-methyl-pent-4-en-2-ol 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: 40.0%

: 405176-39-8
(R)-2-(3,4-Dimethoxy-benzyloxymethyl)-oxirane

: 389123-45-9
(2R,6R)-2-[(2E,6Z)-(R)-4,8-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-octa-2,6-dienyl]-6-((E)-2-bromo-propenyl)-4-methylene-tetrahydro-pyran

: 405176-40-1
(E)-(R)-5-{(2R,6R)-6-[(2E,6Z)-(R)-4,8-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-octa-2,6-dienyl]-4-methylene-tetrahydro-pyran-2-yl}-1-(3,4-dimethoxy-benzyloxy)-4-methyl-pent-4-en-2-ol

Guidance literature:: (2R,6R)-2-[(2E,6Z)-(R)-4,8-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-octa-2,6-dienyl]-6-((E)-2-bromo-propenyl)-4-methylene-tetrahydro-pyran; With tert.-butyl lithium; In diethyl ether; pentane; at -78 - -45 ℃;

With 2-thienylcyano cuprate; In tetrahydrofuran; diethyl ether; pentane; at -78 - 45 ℃;

(R)-2-(3,4-Dimethoxy-benzyloxymethyl)-oxirane; In tetrahydrofuran; diethyl ether; pentane; at -45 - 0 ℃; for 1.75h; Further stages.;
DOI:10.1021/ja020635t

Reference yield:

: 7306-46-9
4-chloromethyl-1,2-dimethoxy-benzene

: 405176-40-1
(E)-(R)-5-{(2R,6R)-6-[(2E,6Z)-(R)-4,8-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-octa-2,6-dienyl]-4-methylene-tetrahydro-pyran-2-yl}-1-(3,4-dimethoxy-benzyloxy)-4-methyl-pent-4-en-2-ol

Guidance literature:: Multi-step reaction with 2 steps

1.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

1.2: 39 percent / tetrabutylammonium iodide / tetrahydrofuran / 15 h / Heating

2.1: t-BuLi / diethyl ether; pentane / -78 - -45 °C

2.2: 2-thienylcyanocuprate / diethyl ether; tetrahydrofuran; pentane / -78 - 45 °C

2.3: 40 percent / diethyl ether; tetrahydrofuran; pentane / 1.75 h / -45 - 0 °C

With tert.-butyl lithium; sodium hydride; In tetrahydrofuran; diethyl ether; pentane;
DOI:10.1021/ja020635t

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 405176-40-1
(E)-(R)-5-{(2R,6R)-6-[(2E,6Z)-(R)-4,8-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-octa-2,6-dienyl]-4-methylene-tetrahydro-pyran-2-yl}-1-(3,4-dimethoxy-benzyloxy)-4-methyl-pent-4-en-2-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 88 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / -78 °C

2.1: 91 percent / 4,4'-di-tert-butylbiphenyl; Li / tetrahydrofuran / -78 °C

3.1: 97 percent / oxalyl chloride; dimethyl sulfoxide; Et₃N / CH₂Cl₂ / -78 - 0 °C

4.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 0.5 h / -78 °C

4.2: 88 percent / tetrahydrofuran; toluene / -78 - 20 °C

5.1: t-BuLi / diethyl ether; pentane / -78 - -45 °C

5.2: 2-thienylcyanocuprate / diethyl ether; tetrahydrofuran; pentane / -78 - 45 °C

5.3: 40 percent / diethyl ether; tetrahydrofuran; pentane / 1.75 h / -45 - 0 °C

With 2,6-dimethylpyridine; oxalyl dichloride; 4,4'-di-tert-butylbiphenyl; tert.-butyl lithium; lithium; potassium hexamethylsilazane; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; pentane; 3.1: Swern oxidation / 4.2: Julia olefination;
DOI:10.1021/ja020635t