(1R,2S)-1-(tert-butyldimethylsilyloxy)-1-[(4R,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]but-3-en-2-ol

Base Information

• Chemical Name: (1R,2S)-1-(tert-butyldimethylsilyloxy)-1-[(4R,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]but-3-en-2-ol
• CAS No.: 1006371-20-5
• Molecular Formula: C₂₁H₃₄O₄Si
• Molecular Weight: 378.584

Synonyms:(1R,2S)-1-(tert-butyldimethylsilyloxy)-1-[(4R,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]but-3-en-2-ol

Chemical Property of (1R,2S)-1-(tert-butyldimethylsilyloxy)-1-[(4R,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]but-3-en-2-ol

Chemical Property:

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Technology Process of (1R,2S)-1-(tert-butyldimethylsilyloxy)-1-[(4R,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]but-3-en-2-ol

There total 2 articles about (1R,2S)-1-(tert-butyldimethylsilyloxy)-1-[(4R,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]but-3-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: 94.0%

(1S)-1-(tert-butyldimethylsilyloxy)-1-[(4R,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]but-3-en-2-one (1006371-19-2) → (1R,2S)-1-(tert-butyldimethylsilyloxy)-1-[(4R,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]but-3-en-2-ol (1006371-20-5)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; In methanol; at -78 ℃; for 1h;

DOI:10.1055/s-2007-990866

Reference yield:

(2S)-(tert-butyldimethylsilyloxy)-[(4R,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]acetaldehyde (1006371-18-1) + vinyl magnesium bromide (1826-67-1) → (1R,2R)-1-(tert-butoxydimethylsilyloxy)-1-[(4R,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]but-3-en-2-ol + (1R,2S)-1-(tert-butyldimethylsilyloxy)-1-[(4R,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]but-3-en-2-ol (1006371-20-5)

Guidance literature:

In tetrahydrofuran; at -78 ℃; for 1h; Title compound not separated from byproducts.;

DOI:10.1055/s-2007-990866

Reference yield: 90.0%

(1R,2S)-1-(tert-butyldimethylsilyloxy)-1-[(4R,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]but-3-en-2-ol (1006371-20-5) + chloromethyl methyl ether (107-30-2) → (4R,5S)-4-[(1R,2S)-1-(tert-butyldimethylsilyloxy)-2-(methoxymethoxy)but-3-enyl]-2,2-dimethyl-5-phenyl-1,3-dioxolane (1006371-21-6)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 5.25h;

DOI:10.1055/s-2007-990866

upstream raw materials:

(2S)-(tert-butyldimethylsilyloxy)-[(4R,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]acetaldehyde

vinyl magnesium bromide

(1S)-1-(tert-butyldimethylsilyloxy)-1-[(4R,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]but-3-en-2-one

Downstream raw materials:

(4R,5S)-4-[(1R,2S)-1-(tert-butyldimethylsilyloxy)-2-(methoxymethoxy)but-3-enyl]-2,2-dimethyl-5-phenyl-1,3-dioxolane

(1R,2S)-1-(tert-butyldimethylsilyloxy)-1-[(4R,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]but-3-en-2-y acrylate

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