(1-phenylmethyl)boronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester

Base Information

• Chemical Name: (1-phenylmethyl)boronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester
• CAS No.: 78922-83-5
• Molecular Formula: C₁₇H₂₃BO₂
• Molecular Weight: 270.179
• Mol file: 78922-83-5.mol

Synonyms:(1-phenylmethyl)boronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester

Chemical Property of (1-phenylmethyl)boronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1-phenylmethyl)boronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester

There total 7 articles about (1-phenylmethyl)boronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester 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: 96.0%

Chloroiodomethane (593-71-5) + (3aS,4S,6S,7aR)-3a,5,5-trimethyl-2-phenylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole (76110-78-6) → (1-phenylmethyl)boronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester (78922-83-5)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; boronic ester and ICH2Cl in rigorously dried THF cooled to -78°Cand stirred under Ar during dropwise addn. of 1.6 M n-BuLi in hexane, kept overnight at 20-25°C; concd. in vac., treated with petroleum ether and concd. aq. NH4Cl, org.phase dried over MgSO4, distilled bulb to bulb in vac.;

DOI:10.1021/om00128a038

Reference yield: 91.0%

pinanediol (18680-27-8) + pinacol benzylboronate (87100-28-5) → (1-phenylmethyl)boronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester (78922-83-5)

Guidance literature:

In diethyl ether; at 20 ℃;

Reference yield: 89.0%

chlorobromomethane (74-97-5) + (3aS,4S,6S,7aR)-3a,5,5-trimethyl-2-phenylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole (76110-78-6) → (1-phenylmethyl)boronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester (78922-83-5)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at -80 - 20 ℃; Inert atmosphere;

upstream raw materials:

pinanediol

benzyl boronic acid

Chloroiodomethane

(3aS,4S,6S,7aR)-3a,5,5-trimethyl-2-phenylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole

Downstream raw materials:

(+)-pinanediol (1R)-1-(N,N-bis(trimethylsilyl)amino)-2-phenylethaneboronate

(R)-2-phenyl-1-((3a5,45,65,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)ethanamine hydrochloride

C₆₉H₉₆BN₇O₁₁

C₆₆H₉₁BN₆O₁₀