(S)-pinanediol [(1R)-(N,N-dimethylcarbamoyloxy)(dimethylphenylsilyl)methyl]boronate

Base Information

Chemical Name:(S)-pinanediol [(1R)-(N,N-dimethylcarbamoyloxy)(dimethylphenylsilyl)methyl]boronate
CAS No.:869218-46-2
Molecular Formula:C₂₂H₃₄BNO₄Si
Molecular Weight:415.413
Hs Code.:

Synonyms:(S)-pinanediol [(1R)-(N,N-dimethylcarbamoyloxy)(dimethylphenylsilyl)methyl]boronate

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Chemical Property of (S)-pinanediol [(1R)-(N,N-dimethylcarbamoyloxy)(dimethylphenylsilyl)methyl]boronate

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Technology Process of (S)-pinanediol [(1R)-(N,N-dimethylcarbamoyloxy)(dimethylphenylsilyl)methyl]boronate

There total 11 articles about (S)-pinanediol [(1R)-(N,N-dimethylcarbamoyloxy)(dimethylphenylsilyl)methyl]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: 43.0%

: 869218-41-7
(dimethylphenylsilyl)methyl N,N-dimethylcarbamate

: 819816-60-9
(S)-pinane-2,3-diol tert-butyl alcohol borate

: 869218-46-2
(S)-pinanediol [(1R)-(N,N-dimethylcarbamoyloxy)(dimethylphenylsilyl)methyl]boronate

: (S)-pinanediol [(1S)-(N,N-dimethylcarbamoyloxy)(dimethylphenylsilyl)methyl]boronate

Guidance literature:: (dimethylphenylsilyl)methyl N,N-dimethylcarbamate; With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; In diethyl ether; cyclohexane; at -78 ℃; for 0.25h;

(S)-pinane-2,3-diol tert-butyl alcohol borate; In diethyl ether; cyclohexane; at -78 ℃; for 1h;
DOI:10.1021/ja051568g

Reference yield:

: 869218-44-0
(dimethylphenylsilyl)methyl (S,S)-N,N-bis(1-phenylethyl)carbamate

: 869218-46-2
(S)-pinanediol [(1R)-(N,N-dimethylcarbamoyloxy)(dimethylphenylsilyl)methyl]boronate

Guidance literature:: Multi-step reaction with 5 steps

1.1: s-BuLi; TMEDA / tetrahydrofuran; cyclohexane / 0.25 h / -78 °C

1.2: 42 percent / tetrahydrofuran; cyclohexane / -78 °C

2.1: 71 percent / LiAlH₄ / diethyl ether / 0.5 h / 0 °C

3.1: aq. H₂O₂; NaHCO₃ / tetrahydrofuran / 5 h / 50 °C

3.2: 86 percent / pentaerythritol; water / tetrahydrofuran

4.1: 83 percent / ethyldiisopropylamine; DMAP / toluene / 36 h / Heating

5.1: TMEDA; s-BuLi / diethyl ether; cyclohexane / 0.25 h / -78 °C

5.2: 25 percent / diethyl ether; cyclohexane / 1 h / -78 °C

With dmap; lithium aluminium tetrahydride; N,N,N,N,-tetramethylethylenediamine; dihydrogen peroxide; sec.-butyllithium; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; cyclohexane; toluene;
DOI:10.1021/ja051568g

Reference yield:

: 869218-63-3
(S)-pinanediol (dimethylphenylsilyl)methylboronate

: 869218-46-2
(S)-pinanediol [(1R)-(N,N-dimethylcarbamoyloxy)(dimethylphenylsilyl)methyl]boronate

Guidance literature:: Multi-step reaction with 3 steps

1.1: aq. H₂O₂; NaHCO₃ / tetrahydrofuran / 50 °C

1.2: 78 percent / pentaerythritol / tetrahydrofuran; H₂O

2.1: 83 percent / ethyldiisopropylamine; DMAP / toluene / 36 h / Heating

3.1: TMEDA; s-BuLi / diethyl ether; cyclohexane / 0.25 h / -78 °C

3.2: 25 percent / diethyl ether; cyclohexane / 1 h / -78 °C

With dmap; N,N,N,N,-tetramethylethylenediamine; dihydrogen peroxide; sec.-butyllithium; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; cyclohexane; toluene;
DOI:10.1021/ja051568g