(3R,4S)-1-(tert-butyl-diphenyl-silanyloxy)-4-(4,4,5,5-tetraphenyl-[1,3,2]dioxaborolan-2-yl)hex-5-en-3-ol

Base Information

• Chemical Name: (3R,4S)-1-(tert-butyl-diphenyl-silanyloxy)-4-(4,4,5,5-tetraphenyl-[1,3,2]dioxaborolan-2-yl)hex-5-en-3-ol
• CAS No.: 928621-18-5
• Molecular Formula: C₄₈H₄₉BO₄Si
• Molecular Weight: 728.811

Synonyms:(3R,4S)-1-(tert-butyl-diphenyl-silanyloxy)-4-(4,4,5,5-tetraphenyl-[1,3,2]dioxaborolan-2-yl)hex-5-en-3-ol

Chemical Property of (3R,4S)-1-(tert-butyl-diphenyl-silanyloxy)-4-(4,4,5,5-tetraphenyl-[1,3,2]dioxaborolan-2-yl)hex-5-en-3-ol

Chemical Property:

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Technology Process of (3R,4S)-1-(tert-butyl-diphenyl-silanyloxy)-4-(4,4,5,5-tetraphenyl-[1,3,2]dioxaborolan-2-yl)hex-5-en-3-ol

There total 2 articles about (3R,4S)-1-(tert-butyl-diphenyl-silanyloxy)-4-(4,4,5,5-tetraphenyl-[1,3,2]dioxaborolan-2-yl)hex-5-en-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:

2-{(E)-3-[Bis-((1S,2R,3S,5S)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-boranyl]-propenyl}-4,4,5,5-tetraphenyl-[1,3,2]dioxaborolane + 3-(tert-butyldiphenylsilyloxy)-1-propanal (112897-03-7) → (3R,4S)-1-(tert-butyl-diphenyl-silanyloxy)-4-(4,4,5,5-tetraphenyl-[1,3,2]dioxaborolan-2-yl)hex-5-en-3-ol (928621-18-5)

Guidance literature:

In dichloromethane; at -78 ℃; for 4h;

DOI:10.1021/ol0629869

Reference yield:

2-allenyl-4,4,5,5-tetraphenyl-1,3,2-dioxaborolane (479579-58-3) → (3R,4S)-1-(tert-butyl-diphenyl-silanyloxy)-4-(4,4,5,5-tetraphenyl-[1,3,2]dioxaborolan-2-yl)hex-5-en-3-ol (928621-18-5)

Guidance literature:

Multi-step reaction with 2 steps

1: CH₂Cl₂ / 0 - 23 °C

2: 5.7 g / CH₂Cl₂ / 4 h / -78 °C

In dichloromethane;

DOI:10.1021/ol0629869

Reference yield: 89.0%

(3R,4S)-1-(tert-butyl-diphenyl-silanyloxy)-4-(4,4,5,5-tetraphenyl-[1,3,2]dioxaborolan-2-yl)hex-5-en-3-ol (928621-18-5) + t-butyldimethylsiyl triflate (69739-34-0) → 2-[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-4-(tert-butyl-diphenyl-silanyloxy)-1-vinyl-butyl]-4,4,5,5-tetraphenyl-[1,3,2]dioxaborolane (928621-19-6)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at -78 - 0 ℃;

DOI:10.1021/ol0629869

upstream raw materials:

3-(tert-butyldiphenylsilyloxy)-1-propanal

2-allenyl-4,4,5,5-tetraphenyl-1,3,2-dioxaborolane

Downstream raw materials:

2-[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-4-(tert-butyl-diphenyl-silanyloxy)-1-vinyl-butyl]-4,4,5,5-tetraphenyl-[1,3,2]dioxaborolane

(3S,4S)-3-(tert-butyl-dimethyl-silanyloxy)-4-{(4R,6S)-6-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-4-(tert-butyl-diphenyl-silanyloxy)-butyl]-2-oxo-[1,3]dioxan-4-yl}-pentanal

(4S,6R)-4-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-4-(tert-butyl-diphenyl-silanyloxy)-butyl]-6-[(1S,2S)-2-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-1-methyl-butyl]-[1,3]dioxan-2-one

(2E,4E,6E,8E)-(11S,12S,13R,15S,17R)-11,17-bis-(tert-butyl-dimethyl-silanyloxy)-19-(tert-butyl-diphenyl-silanyloxy)-13,15-dihydroxy-12-methyl-nonadeca-2,4,6,8-tetraenoic acid methyl ester

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