(1S)-2-(tert-butyldimethylsilyloxy)-1-[(4R,5R,6R)-5-(tert-butyldimethylsilyloxy)-2,2-dimethyl-6-phenyl-[1,3]dioxan-4-yl]ethanol

Base Information

Chemical Name:(1S)-2-(tert-butyldimethylsilyloxy)-1-[(4R,5R,6R)-5-(tert-butyldimethylsilyloxy)-2,2-dimethyl-6-phenyl-[1,3]dioxan-4-yl]ethanol
CAS No.:844473-71-8
Molecular Formula:C₂₆H₄₈O₅Si₂
Molecular Weight:496.835
Hs Code.:

Synonyms:(1S)-2-(tert-butyldimethylsilyloxy)-1-[(4R,5R,6R)-5-(tert-butyldimethylsilyloxy)-2,2-dimethyl-6-phenyl-[1,3]dioxan-4-yl]ethanol

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Chemical Property of (1S)-2-(tert-butyldimethylsilyloxy)-1-[(4R,5R,6R)-5-(tert-butyldimethylsilyloxy)-2,2-dimethyl-6-phenyl-[1,3]dioxan-4-yl]ethanol

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Technology Process of (1S)-2-(tert-butyldimethylsilyloxy)-1-[(4R,5R,6R)-5-(tert-butyldimethylsilyloxy)-2,2-dimethyl-6-phenyl-[1,3]dioxan-4-yl]ethanol

There total 1 articles about (1S)-2-(tert-butyldimethylsilyloxy)-1-[(4R,5R,6R)-5-(tert-butyldimethylsilyloxy)-2,2-dimethyl-6-phenyl-[1,3]dioxan-4-yl]ethanol 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: 75.0%

: 677300-65-1
(4R,5R,6R)-5-(tert-butyldimethylsilyloxy)-4-[(1S)-2-(tert-butyldimethylsilyloxy)-1-benzoyloxyethyl]-2,2-dimethyl-6-phenyl-[1,3]dioxane

: 844473-71-8
(1S)-2-(tert-butyldimethylsilyloxy)-1-[(4R,5R,6R)-5-(tert-butyldimethylsilyloxy)-2,2-dimethyl-6-phenyl-[1,3]dioxan-4-yl]ethanol

Guidance literature:: With potassium carbonate; In methanol; at 20 ℃; for 24h;
DOI:10.1021/jo0483116

Reference yield: 85.0%

: 107-30-2
chloromethyl methyl ether

: 844473-71-8
(1S)-2-(tert-butyldimethylsilyloxy)-1-[(4R,5R,6R)-5-(tert-butyldimethylsilyloxy)-2,2-dimethyl-6-phenyl-[1,3]dioxan-4-yl]ethanol

: 844473-72-9
(4R,5R,6R)-5-(tert-butyldimethylsilyloxy)-4-[(1S)-2-(tert-butyldimethylsilyloxy)-1-(methoxymethoxy)ethyl]-2,2-dimethyl-6-phenyl-[1,3]dioxane

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 12h; Heating;
DOI:10.1021/jo0483116

Reference yield:

: 844473-71-8
(1S)-2-(tert-butyldimethylsilyloxy)-1-[(4R,5R,6R)-5-(tert-butyldimethylsilyloxy)-2,2-dimethyl-6-phenyl-[1,3]dioxan-4-yl]ethanol

: 844473-74-1
(1S,2S)-1-[(4R,5R,6R)-5-(tert-butyldimethylsilyloxy)-2,2-dimethyl-6-phenyl-[1,3]dioxan-4-yl]-1-(methoxymethoxy)pent-4-en-2-ol

Guidance literature:: Multi-step reaction with 4 steps

1: 85 percent / DIPEA / CH₂Cl₂ / 12 h / Heating

2: 94 percent / HF*pyridine; pyridine / tetrahydrofuran / 12 h / 20 °C

3: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

4: 644 mg / diethyl ether / 1 h / -90 °C

With pyridine; oxalyl dichloride; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; 3: Swern oxidation;
DOI:10.1021/jo0483116