2-Cyclohexen-1-ol, 5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-[[[(1,1-dimethylethyl)dimethylsil yl]oxy]methyl]-, (1R,4R,5S)-

Base Information

• Chemical Name: 2-Cyclohexen-1-ol, 5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-[[[(1,1-dimethylethyl)dimethylsil yl]oxy]methyl]-, (1R,4R,5S)-
• CAS No.: 247587-58-2
• Molecular Formula: C19H40O3Si2
• Molecular Weight: 372.696
• Mol file: 247587-58-2.mol

Synonyms:

Chemical Property of 2-Cyclohexen-1-ol, 5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-[[[(1,1-dimethylethyl)dimethylsil yl]oxy]methyl]-, (1R,4R,5S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Cyclohexen-1-ol, 5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-[[[(1,1-dimethylethyl)dimethylsil yl]oxy]methyl]-, (1R,4R,5S)-

There total 7 articles about 2-Cyclohexen-1-ol, 5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-[[[(1,1-dimethylethyl)dimethylsil yl]oxy]methyl]-, (1R,4R,5S)- 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: 91.0%

(4R,5S)-4-tert-butyldimethylsilyloxymethyl-5-tert-butyldimethylsilyloxycyclohex-2-en-1-one (247587-57-1) → (1R,4R,5S)-4-tert-butyldimethylsilyloxymethyl-5-tert-butyldimethylsilyloxycyclohex-2-en-1-ol (247587-58-2)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; In methanol; for 1h;

DOI:10.1021/jo9908288

Reference yield:

(1R,2S,3S,5S)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2-(tert-butyldimethylsilyloxymethyl)cyclohexanol (247587-54-8) → (1R,4R,5S)-4-tert-butyldimethylsilyloxymethyl-5-tert-butyldimethylsilyloxycyclohex-2-en-1-ol (247587-58-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / Et₃N / CH₂Cl₂

2: 76 percent / HCOONH₄ / Pd/C / methanol

3: 48 percent / MnO₂ / CH₂Cl₂

4: 91 percent / NaBH₄; CeCl₃*7H₂O

With manganese(IV) oxide; sodium tetrahydroborate; cerium(III) chloride; ammonium formate; triethylamine; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1081/NCN-100002360

Reference yield:

(1R,2S,3S,5S)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2-(tert-butyldimethylsilyloxymethyl)-1-methanesulfonyloxycyclohexane (247587-55-9) → (1R,4R,5S)-4-tert-butyldimethylsilyloxymethyl-5-tert-butyldimethylsilyloxycyclohex-2-en-1-ol (247587-58-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 76 percent / HCOONH₄ / Pd/C / methanol

2: 48 percent / MnO₂ / CH₂Cl₂

3: 91 percent / NaBH₄; CeCl₃*7H₂O

With manganese(IV) oxide; sodium tetrahydroborate; cerium(III) chloride; ammonium formate; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1081/NCN-100002360

upstream raw materials:

(4R,5S)-4-tert-butyldimethylsilyloxymethyl-5-tert-butyldimethylsilyloxycyclohex-2-en-1-one

(1R,2S,3S,5S)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2-(tert-butyldimethylsilyloxymethyl)cyclohexanol

(1R,2S,3S,5S)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2-(tert-butyldimethylsilyloxymethyl)-1-methanesulfonyloxycyclohexane

tert-butyldimethylsilyl chloride

Downstream raw materials:

9-[(1S,4R,5S)-5-(tert-butyldimethylsilyloxy)-4-(tert-butyldimethylsilyloxymethyl)-2-cyclohexenyl]adenine

9-[(1S,4R,5S)-5-(tert-butyldimethylsilyloxy)-4-(tert-butyldimethylsilyloxymethyl)-2-cyclohexenyl]-2-amino-6-chloropurine

9-[(1S,4R,5S)-5-hydroxy-4-hydroxymethyl-2-cyclohexenyl]adenine

9-[(1R,4S,5R)-3-hydroxy-4-hydroxymethylcyclohexanyl]adenine