(1E,6E)-(3S,4R)-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-ol

Base Information

• Chemical Name: (1E,6E)-(3S,4R)-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-ol
• CAS No.: 372511-43-8
• Molecular Formula: C₃₈H₄₈O₅Si
• Molecular Weight: 612.882

Synonyms:(1E,6E)-(3S,4R)-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-ol

Chemical Property of (1E,6E)-(3S,4R)-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-ol

Chemical Property:

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Safty Information:

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Technology Process of (1E,6E)-(3S,4R)-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-ol

There total 17 articles about (1E,6E)-(3S,4R)-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-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: 100.0%

(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) → (1E,6E)-(3S,4R)-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-ol (372511-43-8)

Guidance literature:

With zinc(II) tetrahydroborate; In diethyl ether; at -40 ℃;

DOI:10.1021/ol010150u

Reference yield:

1-methoxy-3-methyl-1, 3-butadiene (54717-57-6) → (1E,6E)-(3S,4R)-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-ol (372511-43-8)

Guidance literature:

Multi-step reaction with 5 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

5.1: 100 percent / Zn(BH₄)2 / diethyl ether / -40 °C

With triethylsilane; zinc(II) tetrahydroborate; 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)-(3S,4R)-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-ol (372511-43-8)

Guidance literature:

Multi-step reaction with 12 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

8.1: 100 percent / Zn(BH₄)2 / diethyl ether / -40 °C

With 1H-imidazole; lithium aluminium tetrahydride; zinc(II) tetrahydroborate; 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:

(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

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

O-(4-methoxybenzyl)-trichloroacetimidate

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

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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