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

Base Information

• Chemical Name: (1S,2R,3S,4R)-2,3-O-(2-methylallylboryl)-2-phenyl-1,7,7-trimethylbornanediol
• CAS No.: 604774-96-1
• Molecular Formula: C₂₀H₂₇BO₂
• Molecular Weight: 310.244
• Mol file: 604774-96-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about (1S,2R,3S,4R)-2,3-O-(2-methylallylboryl)-2-phenyl-1,7,7-trimethylbornanediol 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: 70.0%

2-methylallylmagnesium chloride (5674-01-1) + (1R,2S,3R,4S)-2-phenyl-1,7,7-trimethylbornanediol → (1S,2R,3S,4R)-2,3-O-(2-methylallylboryl)-2-phenyl-1,7,7-trimethylbornanediol (604774-96-1)

Guidance literature:

(1R,2S,3R,4S)-2-phenyl-1,7,7-trimethylbornanediol; With triisopropylborane; In diethyl ether; at 20 ℃; for 0.5h;

2-methylallylmagnesium chloride; In tetrahydrofuran; diethyl ether; at -78 - 20 ℃; for 4.5h;

DOI:10.1055/s-2004-822359

Reference yield:

(1R,2S,3R,4S)-2,3-O-[(Z)-2-butenylboryl]-2-phenyl-1,7,7-trimethylbornanediol → (1S,2R,3S,4R)-2,3-O-(2-methylallylboryl)-2-phenyl-1,7,7-trimethylbornanediol (604774-96-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Sc(OTf)3; 2-octynal / CH₂Cl₂ / 24 h / -78 °C

1.2: aq. NaOH; H₂O₂ / CH₂Cl₂; tetrahydrofuran / 16 h

2.1: (i-Pr)3B / diethyl ether / 0.5 h / 20 °C

2.2: 70 percent / diethyl ether; tetrahydrofuran / 4.5 h / -78 - 20 °C

With oct-2-ynal; triisopropylborane; scandium tris(trifluoromethanesulfonate); In diethyl ether; dichloromethane;

DOI:10.1055/s-2004-822359

Reference yield: 77.0%

3-(tert-butyldiphenylsilyloxy)-1-propanal (112897-03-7) + (1S,2R,3S,4R)-2,3-O-(2-methylallylboryl)-2-phenyl-1,7,7-trimethylbornanediol (604774-96-1) → (3R)-1-O-(t-butyldiphenylsilyl)-1,3-dihydroxy-5-methylhex-5-ene (148585-93-7)

Guidance literature:

With scandium tris(trifluoromethanesulfonate); In dichloromethane; at -78 ℃; for 16h;

DOI:10.1055/s-2004-822359

upstream raw materials:

2-methylallylmagnesium chloride

Downstream raw materials:

(2R)-1-(benzyloxy)-4-methyl-4-penten-2-ol

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

(+)-(R)-3-methyl-1-phenyl-3-buten-1-ol

(1R)-1-cyclohexyl-3-methylbut-3-en-1-ol