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

Base Information

Chemical Name:(+)-pinanediol (1R)-1-(N,N-bis(trimethylsilyl)amino)-2-phenylethaneboronate
CAS No.:78902-04-2
Molecular Formula:C₂₄H₄₂BNO₂Si₂
Molecular Weight:443.585
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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

Chemical Property:

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

There total 4 articles about (+)-pinanediol (1R)-1-(N,N-bis(trimethylsilyl)amino)-2-phenylethaneboronate 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:

: 4039-32-1
lithium hexamethyldisilazane

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

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

Guidance literature:: In tetrahydrofuran; soln. of α-chloro ester was cooled to -78°C, treated with LiN(SiMe3)2 in THF, mixt. was stirred overnight at 20-25°C; product was not isolated in pure state;
DOI:10.1021/om00082a019

Reference yield:

: 78922-83-5
(1-phenylmethyl)boronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester

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

Guidance literature:: Multi-step reaction with 2 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -110 - -95 °C / Inert atmosphere

1.2: Matteson Homologation / -100 - -95 °C / Inert atmosphere

1.3: Matteson Homologation / 1 h / -100 - 20 °C / Inert atmosphere

2.1: tetrahydrofuran / 1 h / -78 - 20 °C / Inert atmosphere

With n-butyllithium; In tetrahydrofuran; hexane; 1.1: |Matteson Homologation;
DOI:10.1021/acs.jmedchem.1c00604

Reference yield:

: 87100-28-5
pinacol benzylboronate

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

Guidance literature:: Multi-step reaction with 3 steps

1.1: tert-butyl methyl ether / 20 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -110 - -95 °C / Inert atmosphere

2.2: Matteson Homologation / -100 - -95 °C / Inert atmosphere

2.3: Matteson Homologation / 1 h / -100 - 20 °C / Inert atmosphere

3.1: tetrahydrofuran / 1 h / -78 - 20 °C / Inert atmosphere

With n-butyllithium; In tetrahydrofuran; hexane; tert-butyl methyl ether; 2.1: |Matteson Homologation;
DOI:10.1021/acs.jmedchem.1c00604