(1E,6E)-(R)-8-(tert-Butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-1-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-1,6-dien-3-one

Base Information

• Chemical Name: (1E,6E)-(R)-8-(tert-Butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-1-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-1,6-dien-3-one
• CAS No.: 372511-42-7
• Molecular Formula: C₃₈H₄₆O₅Si
• Molecular Weight: 610.866

Synonyms:(1E,6E)-(R)-8-(tert-Butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-1-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-1,6-dien-3-one

Chemical Property of (1E,6E)-(R)-8-(tert-Butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-1-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-1,6-dien-3-one

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Technology Process of (1E,6E)-(R)-8-(tert-Butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-1-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-1,6-dien-3-one

There total 15 articles about (1E,6E)-(R)-8-(tert-Butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-1-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-1,6-dien-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: 87.0%

(2S)-4-methyl-3,6-dihydro-2H-pyran-2-carbaldehyde (218898-32-9) + (E)-(R)-7-(tert-Butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxy)-hept-5-en-2-one (372511-38-1) → (1E,6E)-(R)-8-(tert-Butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-1-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-1,6-dien-3-one (372511-42-7)

Guidance literature:

(2S)-4-methyl-3,6-dihydro-2H-pyran-2-carbaldehyde; (E)-(R)-7-(tert-Butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxy)-hept-5-en-2-one; With dicyclohexylboron chloride; triethylamine; In diethyl ether; at -78 ℃;

With dihydrogen peroxide;

With methanesulfonyl chloride; triethylamine; In dichloromethane; Further stages.;

DOI:10.1021/ol010150u

Reference yield:

1-methoxy-3-methyl-1, 3-butadiene (54717-57-6) → (1E,6E)-(R)-8-(tert-Butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-1-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-1,6-dien-3-one (372511-42-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 71 percent / 4 Angstroem molecular sieves / chiral Cr(III) catalyst

2.1: Et₃SiH; BF₃*OEt₂ / CH₂Cl₂

2.2: 72 percent / HCl / CH₂Cl₂; methanol

3.1: 80 percent / (COCl)2; DMSO; Et₃N

4.1: (c-Hex)2BCl; Et₃N / diethyl ether / -78 °C

4.2: H₂o2

4.3: 87 percent / MsCl; Et₃N / CH₂Cl₂

With triethylsilane; oxalyl dichloride; 4 A molecular sieve; boron trifluoride diethyl etherate; dicyclohexylboron chloride; dimethyl sulfoxide; triethylamine; chiral Cr(III) catalyst; In diethyl ether; dichloromethane; 1.1: hetero-Diels-Alder reaction / 3.1: Swern oxidation;

DOI:10.1021/ol010150u

Reference yield:

O-(4-methoxybenzyl)-trichloroacetimidate (89238-99-3) → (1E,6E)-(R)-8-(tert-Butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-1-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-1,6-dien-3-one (372511-42-7)

Guidance literature:

Multi-step reaction with 11 steps

1.1: TfOH / diethyl ether

2.1: LiAlH₄ / tetrahydrofuran

3.1: iPr₂NEt; LiCl / acetonitrile

4.1: DIBAL / CH₂Cl₂ / -78 °C

5.1: imidazole / CH₂Cl₂

6.1: p-TsOH / methanol

7.1: (c-Hex)2BCl; Et₃N / diethyl ether / -78 °C

7.2: H₂o2

7.3: 87 percent / MsCl; Et₃N / CH₂Cl₂

With 1H-imidazole; lithium aluminium tetrahydride; trifluorormethanesulfonic acid; dicyclohexylboron chloride; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetonitrile; 3.1: Dess-Martin oxidation / 4.1: Horner-Wadsworth-Emmons olefination / 8.1: Swern oxidation / 9.1: Grignard reaction / 10.1: Swern oxidation;

DOI:10.1021/ol010150u

upstream raw materials:

(2S)-4-methyl-3,6-dihydro-2H-pyran-2-carbaldehyde

(E)-(R)-7-(tert-Butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxy)-hept-5-en-2-one

1-methoxy-3-methyl-1, 3-butadiene

O-(4-methoxybenzyl)-trichloroacetimidate

Downstream raw materials:

(Z)-4-{(2R,6R)-6-[(7E,12E)-(2R,10R,11S)-6,11-Bis-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-2-methyl-13-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-oxo-trideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid methyl ester

(Z)-4-{(2R,6R)-6-[(7E,12E)-(2R,10R,11S)-11-(tert-Butyl-dimethyl-silanyloxy)-6-hydroxy-10-(4-methoxy-benzyloxy)-2-methyl-13-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-oxo-trideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid methyl ester

(2E,7E)-(5R,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-8-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-2,7-dien-1-ol

(2E,7E)-(5R,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-8-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-2,7-dienal

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