(+)-pinanediol (R)-1-acetamido-2-phenylethane-1-boronate

Base Information

Chemical Name:(+)-pinanediol (R)-1-acetamido-2-phenylethane-1-boronate
CAS No.:78902-05-3
Molecular Formula:C₂₀H₂₈BNO₃
Molecular Weight:341.258
Hs Code.:

Synonyms:(+)-pinanediol (R)-1-acetamido-2-phenylethane-1-boronate

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

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

There total 3 articles about (+)-pinanediol (R)-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: 81.0%

: 4039-32-1
lithium hexamethyldisilazane

: 78902-03-1
1-(S)-chloro-2-phenylethylboronic acid (1S,2S,3R,5S)-(+)-pinane-2,3-glycol ester

: 78902-05-3
(+)-pinanediol (R)-1-acetamido-2-phenylethane-1-boronate

Guidance literature:: With acetic anhydride; acetic acid; In tetrahydrofuran; (N2); stirring (-78°C), warming and stirring (20°C, 10 h),cooling (-78°C), addn. CH3COOH and (CH3CO)2O, stirring (20.degre e.C, 24 h); rot. evapn., layer sepn., extn. (EtOAc), washing (NaHCO3, H2O), drying (MgSO4), recrystn. (EtOAc/CHCl3);
DOI:10.1021/ja952816j

Reference yield: 63.0%

: 78902-03-1
1-(S)-chloro-2-phenylethylboronic acid (1S,2S,3R,5S)-(+)-pinane-2,3-glycol ester

: 78902-05-3
(+)-pinanediol (R)-1-acetamido-2-phenylethane-1-boronate

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; soln. chromd., product recrystd. from CH2Cl2 3 times;
DOI:10.1021/ja00407a051

Reference yield:

: 78902-04-2
(+)-pinanediol (1R)-1-(N,N-bis(trimethylsilyl)amino)-2-phenylethaneboronate

: 78902-05-3
(+)-pinanediol (R)-1-acetamido-2-phenylethane-1-boronate

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); elem. anal.;
DOI:10.1021/om00082a019