(3R)-1-O-(t-butyldiphenylsilyl)-1,3-dihydroxy-5-methylhex-5-ene

Base Information

• Chemical Name: (3R)-1-O-(t-butyldiphenylsilyl)-1,3-dihydroxy-5-methylhex-5-ene
• CAS No.: 148585-93-7
• Molecular Formula: C₂₃H₃₂O₂Si
• Molecular Weight: 368.591
• Mol file: 148585-93-7.mol

Synonyms:(3R)-1-O-(t-butyldiphenylsilyl)-1,3-dihydroxy-5-methylhex-5-ene

Chemical Property of (3R)-1-O-(t-butyldiphenylsilyl)-1,3-dihydroxy-5-methylhex-5-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R)-1-O-(t-butyldiphenylsilyl)-1,3-dihydroxy-5-methylhex-5-ene

There total 6 articles about (3R)-1-O-(t-butyldiphenylsilyl)-1,3-dihydroxy-5-methylhex-5-ene 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: 99.0%

3-(tert-butyldiphenylsilyloxy)-1-propanal (112897-03-7) + 4,4,5,5-tetramethyl-2-(2-methylallyl)-1,3,2-dioxaborolane (167773-10-6) → (3R)-1-O-(t-butyldiphenylsilyl)-1,3-dihydroxy-5-methylhex-5-ene (148585-93-7)

Guidance literature:

4,4,5,5-tetramethyl-2-(2-methylallyl)-1,3,2-dioxaborolane; With (1R,2R)-1,2-bis(2-cyclooctylphenyl)ethane-1,2-diol; tin(IV) chloride; sodium carbonate; In dichloromethane; toluene; at -78 ℃; for 0.5h; Molecular sieve;

3-(tert-butyldiphenylsilyloxy)-1-propanal; In dichloromethane; toluene; at -78 ℃; for 5h; optical yield given as %ee;

DOI:10.1021/ja8016076

Reference yield: 99.0%

(3R)-1-O-(t-butyldiphenylsilyl)-3-O-(trimethylsilyl)-1,3-dihydroxy-5-methylhex-5-ene (148585-92-6) → (3R)-1-O-(t-butyldiphenylsilyl)-1,3-dihydroxy-5-methylhex-5-ene (148585-93-7)

Guidance literature:

With pyridinium p-toluenesulfonate; In methanol; for 15h; Ambient temperature;

DOI:10.1016/S0957-4166(00)86085-1

Reference yield: 77.0%

3-(tert-butyldiphenylsilyloxy)-1-propanal (112897-03-7) + (1R,2S,3R,4S)-2,3-O-(2-methylallylboryl)-2-phenyl-1,7,7-trimethylbornanediol (604774-85-8) → (3R)-1-O-(t-butyldiphenylsilyl)-1,3-dihydroxy-5-methylhex-5-ene (148585-93-7)

Guidance literature:

3-(tert-butyldiphenylsilyloxy)-1-propanal; (1R,2S,3R,4S)-2,3-O-(2-methylallylboryl)-2-phenyl-1,7,7-trimethylbornanediol; With scandium tris(trifluoromethanesulfonate); In dichloromethane; at -78 ℃; for 16h;

With diisobutylaluminium hydride; In dichloromethane; toluene; at -78 ℃; for 0.5h;

DOI:10.1021/ja036807j

upstream raw materials:

(2S)-O-(tert-butyldiphenylsilyl)-1,2-epoxybutan-4-ol

(3R)-1-O-(t-butyldiphenylsilyl)-3-O-(trimethylsilyl)-1,3-dihydroxy-5-methylhex-5-ene

3-(tert-butyldiphenylsilyloxy)-1-propanal

(1R,2S,3R,4S)-2,3-O-(2-methylallylboryl)-2-phenyl-1,7,7-trimethylbornanediol

Downstream raw materials:

(3S,5R)-1-((tert-butyldiphenylsilyl)oxy)-5-methyloct-7-ene-3,5-diol

(2S,4S)-6-O-(t-butyldiphenylsilyl)-1,2-epoxy-2-methylhexane-4,6-diol

(4S,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-iodomethyl-4-methyl-[1,3]dioxan-2-one