(1R,3S,5S)-1-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-methylene-5-triisopropylsilanyloxy-cyclohexane-1,3-diol

Base Information

• Chemical Name: (1R,3S,5S)-1-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-methylene-5-triisopropylsilanyloxy-cyclohexane-1,3-diol
• CAS No.: 874349-99-2
• Molecular Formula: C₂₄H₅₀O₄Si₂
• Molecular Weight: 458.83
• Mol file: 874349-99-2.mol

Synonyms:(1R,3S,5S)-1-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-methylene-5-triisopropylsilanyloxy-cyclohexane-1,3-diol

Chemical Property of (1R,3S,5S)-1-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-methylene-5-triisopropylsilanyloxy-cyclohexane-1,3-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3S,5S)-1-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-methylene-5-triisopropylsilanyloxy-cyclohexane-1,3-diol

There total 2 articles about (1R,3S,5S)-1-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-methylene-5-triisopropylsilanyloxy-cyclohexane-1,3-diol 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: 93.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (1R,3S,5S)-1-(2-hydroxyethyl)-5-tri-isopropylsilyloxy-2-methylenecyclohexan-1,3-diol (773889-88-6) → (1R,3S,5S)-1-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-methylene-5-triisopropylsilanyloxy-cyclohexane-1,3-diol (874349-99-2)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; toluene; at 20 ℃; for 15h;

DOI:10.1002/chem.200500640

Reference yield:

(6R,7S,8S,10S)-7,8-epoxy-2,2,7-trimethyl-10-tri-isopropylsilyloxy-1,3-dioxaspiro[5.5]undecane (773889-91-1) → (1R,3S,5S)-1-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-methylene-5-triisopropylsilanyloxy-cyclohexane-1,3-diol (874349-99-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 61 percent / 2,2,6,6-tetramethylpiperidine; n-BuLi; Et₂AlCl / hexane; benzene; toluene / 0.75 h / 0 °C

2: 93 percent / imidazole / toluene; dimethylformamide / 15 h / 20 °C

With 2,2,6,6-tetramethyl-piperidine; 1H-imidazole; n-butyllithium; diethylaluminium chloride; In hexane; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1002/chem.200500640

Reference yield: 86.0%

(1R,3S,5S)-1-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-methylene-5-triisopropylsilanyloxy-cyclohexane-1,3-diol (874349-99-2) + benzyl bromide (100-39-0) → (1R,3S,5S)-1-(2-tert-butyldimethylsilyloxyethyl)-3-benzyloxy-5-triisopropylsilyloxy-2-methylencyclohexan-1-ol (874350-02-4)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1002/chem.200500640

upstream raw materials:

tert-butyldimethylsilyl chloride

(1R,3S,5S)-1-(2-hydroxyethyl)-5-tri-isopropylsilyloxy-2-methylenecyclohexan-1,3-diol

(6R,7S,8S,10S)-7,8-epoxy-2,2,7-trimethyl-10-tri-isopropylsilyloxy-1,3-dioxaspiro[5.5]undecane

Downstream raw materials:

(1R,3S,5S)-1-(2-tert-butyldimethylsilyloxyethyl)-3-benzyloxy-5-triisopropylsilyloxy-2-methylencyclohexan-1-ol

(3S,4R,6S,8S)-4-(2-tert-butyldimethylsilyloxyethyl)-8-benzyloxy-4-triethylsilyloxy-6-(triisopropyl)silyloxy-1-oxaspiro[2.5]octane

(1S,2R,4S,6S)-6-Benzyloxy-2-(2-hydroxy-ethyl)-1-(2-phenyl-[1,3]dithian-2-ylmethyl)-2-triethylsilanyloxy-4-triisopropylsilanyloxy-cyclohexanol

(1S,2R,4S,6S)-6-Benzyloxy-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-(2-phenyl-[1,3]dithian-2-ylmethyl)-2-triethylsilanyloxy-4-triisopropylsilanyloxy-cyclohexanol