6-(tert-butyl-dimethyl-silanyloxy)-1-[4-(tert-butyl-dimethyl-silanyloxy)-1,2,2-trimethyl-cyclopentyl]-1-(4-methoxy-benzyloxymethoxy)-4-methyl-hex-4-en-3-ol

Base Information

• Chemical Name: 6-(tert-butyl-dimethyl-silanyloxy)-1-[4-(tert-butyl-dimethyl-silanyloxy)-1,2,2-trimethyl-cyclopentyl]-1-(4-methoxy-benzyloxymethoxy)-4-methyl-hex-4-en-3-ol
• CAS No.: 473670-94-9
• Molecular Formula: C₃₆H₆₆O₆Si₂
• Molecular Weight: 651.087
• Mol file: 473670-94-9.mol

Synonyms:6-(tert-butyl-dimethyl-silanyloxy)-1-[4-(tert-butyl-dimethyl-silanyloxy)-1,2,2-trimethyl-cyclopentyl]-1-(4-methoxy-benzyloxymethoxy)-4-methyl-hex-4-en-3-ol

Chemical Property of 6-(tert-butyl-dimethyl-silanyloxy)-1-[4-(tert-butyl-dimethyl-silanyloxy)-1,2,2-trimethyl-cyclopentyl]-1-(4-methoxy-benzyloxymethoxy)-4-methyl-hex-4-en-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-(tert-butyl-dimethyl-silanyloxy)-1-[4-(tert-butyl-dimethyl-silanyloxy)-1,2,2-trimethyl-cyclopentyl]-1-(4-methoxy-benzyloxymethoxy)-4-methyl-hex-4-en-3-ol

There total 12 articles about 6-(tert-butyl-dimethyl-silanyloxy)-1-[4-(tert-butyl-dimethyl-silanyloxy)-1,2,2-trimethyl-cyclopentyl]-1-(4-methoxy-benzyloxymethoxy)-4-methyl-hex-4-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: 95.0%

(E)-2-bromo-4-(tert-butyldimethylsilyloxy)-2-butene (143236-64-0) + 3-[(1R,4S)-4-tert-butyldimethylsilyloxy-1,2,2-trimethylcyclopentyl]-3-{[(4-methoxyphenyl)methoxy]methoxy}propanal (314774-17-9) → 6-(tert-butyl-dimethyl-silanyloxy)-1-[4-(tert-butyl-dimethyl-silanyloxy)-1,2,2-trimethyl-cyclopentyl]-1-(4-methoxy-benzyloxymethoxy)-4-methyl-hex-4-en-3-ol (473670-94-9)

Guidance literature:

(E)-2-bromo-4-(tert-butyldimethylsilyloxy)-2-butene; With tert.-butyl lithium; In diethyl ether; pentane; at -78 ℃; for 0.166667h;

3-[(1R,4S)-4-tert-butyldimethylsilyloxy-1,2,2-trimethylcyclopentyl]-3-{[(4-methoxyphenyl)methoxy]methoxy}propanal; In diethyl ether; pentane; at -78 ℃;

DOI:10.1039/b201228f

Reference yield:

2-[(4R)-4-tert-butyldimethylsilyloxy-2,6,6-trimethylcyclohex-1-enyl]ethanol (408357-89-1) → 6-(tert-butyl-dimethyl-silanyloxy)-1-[4-(tert-butyl-dimethyl-silanyloxy)-1,2,2-trimethyl-cyclopentyl]-1-(4-methoxy-benzyloxymethoxy)-4-methyl-hex-4-en-3-ol (473670-94-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 93 percent / pyridine / 16 h / 20 °C

2.1: 28 percent / MCPBA / CH₂Cl₂ / 1 h / 0 °C

3.1: 63 percent / (p-BrC₆H₄)3N(+)*SbCl₆(-) / CH₂Cl₂ / 0.5 h / 20 °C

4.1: 78 percent / NaBH₄ / methanol / 0.5 h / 0 °C

5.1: 80 percent / (i-Pr)2NEt / CH₂Cl₂ / 16 h / 20 °C

6.1: 99 percent / LAH / diethyl ether / 0.5 h / 0 °C

7.1: 93 percent / o-iodoxybenzoic acid / dimethylsulfoxide / 1 h / 20 °C

8.1: t-BuLi / diethyl ether; pentane / 0.17 h / -78 °C

8.2: 95 percent / diethyl ether; pentane / -78 °C

With pyridine; sodium tetrahydroborate; lithium aluminium tetrahydride; tert.-butyl lithium; tris(p-bromophenylammoniumyl) hexachloroantimonate; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; pentane;

DOI:10.1039/b201228f

Reference yield:

2-[(4R)-4-tert-butyldimethylsilyloxy-2,6,6,-trimethylcyclohex-1-enyl]ethyl acetate (314774-15-7) → 6-(tert-butyl-dimethyl-silanyloxy)-1-[4-(tert-butyl-dimethyl-silanyloxy)-1,2,2-trimethyl-cyclopentyl]-1-(4-methoxy-benzyloxymethoxy)-4-methyl-hex-4-en-3-ol (473670-94-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 28 percent / MCPBA / CH₂Cl₂ / 1 h / 0 °C

2.1: 63 percent / (p-BrC₆H₄)3N(+)*SbCl₆(-) / CH₂Cl₂ / 0.5 h / 20 °C

3.1: 78 percent / NaBH₄ / methanol / 0.5 h / 0 °C

4.1: 80 percent / (i-Pr)2NEt / CH₂Cl₂ / 16 h / 20 °C

5.1: 99 percent / LAH / diethyl ether / 0.5 h / 0 °C

6.1: 93 percent / o-iodoxybenzoic acid / dimethylsulfoxide / 1 h / 20 °C

7.1: t-BuLi / diethyl ether; pentane / 0.17 h / -78 °C

7.2: 95 percent / diethyl ether; pentane / -78 °C

With sodium tetrahydroborate; lithium aluminium tetrahydride; tert.-butyl lithium; tris(p-bromophenylammoniumyl) hexachloroantimonate; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; pentane;

DOI:10.1039/b201228f

upstream raw materials:

(E)-2-bromo-4-(tert-butyldimethylsilyloxy)-2-butene

3-[(1R,4S)-4-tert-butyldimethylsilyloxy-1,2,2-trimethylcyclopentyl]-3-{[(4-methoxyphenyl)methoxy]methoxy}propanal

para-methoxybenzyl chloride

tert-butyldimethylsilyl chloride

Downstream raw materials:

all-E mytiloxanthin

(4E)-6-tert-butyldimethylsilyloxy-1-[(1R,4S)-4-tert-butyldimethylsilyloxy-1,2,2-trimethylcyclopentyl]-1-{[(4-methoxyphenyl)methoxy]methoxy}-4-methylhex-4-en-3-one