1-(tert-butyl-diphenyl-silanyloxy)-2(S),4(S)-dimethyl-hex-5-en-3(R)-ol

Base Information

• Chemical Name: 1-(tert-butyl-diphenyl-silanyloxy)-2(S),4(S)-dimethyl-hex-5-en-3(R)-ol
• CAS No.: 106357-26-0
• Molecular Formula: C₂₄H₃₄O₂Si
• Molecular Weight: 382.618
• Mol file: 106357-26-0.mol

Synonyms:1-(tert-butyl-diphenyl-silanyloxy)-2(S),4(S)-dimethyl-hex-5-en-3(R)-ol

Chemical Property of 1-(tert-butyl-diphenyl-silanyloxy)-2(S),4(S)-dimethyl-hex-5-en-3(R)-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(tert-butyl-diphenyl-silanyloxy)-2(S),4(S)-dimethyl-hex-5-en-3(R)-ol

There total 34 articles about 1-(tert-butyl-diphenyl-silanyloxy)-2(S),4(S)-dimethyl-hex-5-en-3(R)-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: 93.0%

(2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropanal (92817-88-4) + (Z)-crotyltri-n-butylstannane (35998-94-8) → 1-(tert-butyl-diphenyl-silanyloxy)-2(S),4(S)-dimethyl-hex-5-en-3(R)-ol (106357-26-0)

Guidance literature:

titanium tetrachloride; In dichloromethane; at -85 ℃;

DOI:10.1080/00397910801929358

Reference yield: 74.0%

(2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropanal (92817-88-4) + (3aS,9aS)-2-((Z)-But-2-enyl)-5,8-bis-(2,2,2-trifluoro-ethyl)-hexahydro-[1,3,2]dioxaborolo[4,5-f][1,4]diazocine-4,9-dione → 1-(tert-butyl-diphenyl-silanyloxy)-2(S),4(S)-dimethyl-hex-5-en-3(R)-ol (106357-26-0)

Guidance literature:

With 4 A molecular sieve; In tetrahydrofuran; at -78 - 23 ℃; for 10h;

DOI:10.1021/jo00117a036

Reference yield: 65.0%

(2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropanal (92817-88-4) + (S,S)-diisopropyl tartrate (E)-crotylboronate (99745-86-5,106357-20-4,106357-33-9,99687-40-8) → (3R,4R,5S)-6-(tert-butyldiphenylsiloxy)-4-hydroxy-3,5-dimethylhexan-1-ene (91751-27-8,91797-99-8,91798-00-4,91798-01-5,106357-24-8,106357-26-0,106357-27-1,106357-25-9) + (3S,4S,5S)-6-(tert-butyldiphenylsiloxy)-4-hydroxy-3,5-dimethylhexan-1-ene (106357-24-8)

Guidance literature:

In toluene; at -78 ℃; for 2.5h; diastereoselective reaction; Molecular sieve;

DOI:10.1016/j.tet.2016.11.050

upstream raw materials:

(R,R)-diisopropyl tartrate (Z)-crotylboronate

(2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropanal

(R,R)-[(E)-2-butenyl]diisopropyl tartrate boronate

(4S,5S)-2-[(2Z)-2-butenyl]-1,3,2-dioxaborolane-4,5-dicarboxylic acid bis(1-methylethyl) ester

Downstream raw materials:

(2R,5S,6S)-6-[(1S)-2-(p-toluenesulfonyl)-1-methylethyl]-5-methyl-2-methoxy-5,6-dihydro-2H-pyran

(2R,5S,6S)-6-[(1S)-2-(tert-butyldiphenylsilyloxy)-1-methylethyl]-5-methyl-2-methoxy-5,6-dihydro-2H-pyran

(5S,6R)-6-[(1S)-2-(tert-butyl-diphenylsilanyloxy)-1-methyl-ethyl]-5-methyl-5,6-dihydro-pyran-2-one

(2R,3S,6S)-6-[(2S,3S,6R)-(6-methoxy-3-methyl-3,6-dihydro-2H-pyran-2-yl)-1-(4-methoxybenzyloxy)]-2-methylheptan-3-ol