(-)-pinanediol (S)-1-acetamido-2-phenylethane-1-boronate

Base Information

• Chemical Name: (-)-pinanediol (S)-1-acetamido-2-phenylethane-1-boronate
• CAS No.: 88824-39-9
• Molecular Formula: C₂₀H₂₈BNO₃
• Molecular Weight: 341.258
• Mol file: 88824-39-9.mol

Synonyms:

Chemical Property of (-)-pinanediol (S)-1-acetamido-2-phenylethane-1-boronate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-pinanediol (S)-1-acetamido-2-phenylethane-1-boronate

There total 2 articles about (-)-pinanediol (S)-1-acetamido-2-phenylethane-1-boronate 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:

(R)-(1-chloro-2-phenylethyl)boronic acid (1R,2R,3S,5R)-(-)-2,3-pinanediol ester (88824-37-7) → (-)-pinanediol (S)-1-acetamido-2-phenylethane-1-boronate (88824-39-9)

Guidance literature:

With LiN(SiMe₃)2; acetic anhydride; acetic acid; chloro-compd. treated in situ with LiN(SiMe3)2 followed by acetic anhydride and acetic acid;

DOI:10.1021/ja00407a051

Reference yield:

pinanediol 1-(bis(trimethylsilyl)amino)-2-phenylethane-1-boronate (88824-38-8) → (-)-pinanediol (S)-1-acetamido-2-phenylethane-1-boronate (88824-39-9)

Guidance literature:

With acetic anhydride; acetic acid; In tetrahydrofuran; a soln. of α-amino ester was cooled to -78°C, treated withan excess of Ac2O followed by glacial AcOH, stirred at 20-25°C for 10-12 h; soln. was concd. under vac., residue chromd. through a short SiO2 column with 5-10% EtOAc-hexane, recrystd. from CH2Cl2 to const. rotation (3 times);

DOI:10.1021/om00082a019

upstream raw materials:

(R)-(1-chloro-2-phenylethyl)boronic acid (1R,2R,3S,5R)-(-)-2,3-pinanediol ester

pinanediol 1-(bis(trimethylsilyl)amino)-2-phenylethane-1-boronate