(-)-pinanediol (1R,2R)-2-benzyloxy-4-[tert-butoxycarbonyl]-1-chlorobutaneboronate

Base Information

Chemical Name:(-)-pinanediol (1R,2R)-2-benzyloxy-4-[tert-butoxycarbonyl]-1-chlorobutaneboronate
CAS No.:852509-20-7
Molecular Formula:C₂₆H₃₈BClO₅
Molecular Weight:476.849
Hs Code.:

Synonyms:

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Chemical Property of (-)-pinanediol (1R,2R)-2-benzyloxy-4-[tert-butoxycarbonyl]-1-chlorobutaneboronate

Chemical Property:

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Technology Process of (-)-pinanediol (1R,2R)-2-benzyloxy-4-[tert-butoxycarbonyl]-1-chlorobutaneboronate

There total 7 articles about (-)-pinanediol (1R,2R)-2-benzyloxy-4-[tert-butoxycarbonyl]-1-chlorobutaneboronate 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:

: 852509-18-3
(-)-pinanediol (1S)-1-benzyloxy-3-[tert-butoxycarbonyl]propaneboronate

: 75-09-2
dichloromethane

: 852509-20-7
(-)-pinanediol (1R,2R)-2-benzyloxy-4-[tert-butoxycarbonyl]-1-chlorobutaneboronate

Guidance literature:: dichloromethane; With n-butyllithium; In tetrahydrofuran; hexane; at -100 ℃;

(-)-pinanediol (1S)-1-benzyloxy-3-[tert-butoxycarbonyl]propaneboronate; With zinc(II) chloride; In tetrahydrofuran; diethyl ether; hexane; at -100 - 20 ℃;
DOI:10.1016/j.tet.2005.02.069

Reference yield:

: chloro-methylboronic acid (-)-pinanediolato diester

: 852509-20-7
(-)-pinanediol (1R,2R)-2-benzyloxy-4-[tert-butoxycarbonyl]-1-chlorobutaneboronate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 86 percent / sodium iodide / acetone / 3 h / 20 °C

2.1: 65 percent / LDA / tetrahydrofuran / -78 - 20 °C

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.92 h / -100 °C

3.2: zinc chloride / tetrahydrofuran; hexane; diethyl ether / -100 - 20 °C

4.1: 44 percent / n-butyllithium / tetrahydrofuran; hexane / 2 h / Heating

5.1: n-butyllithium / tetrahydrofuran; hexane / -100 °C

5.2: zinc chloride / tetrahydrofuran; hexane; diethyl ether / -100 - 20 °C

With n-butyllithium; sodium iodide; lithium diisopropyl amide; In tetrahydrofuran; hexane; acetone;
DOI:10.1016/j.tet.2005.02.069

Reference yield:

: 852509-27-4
(-)-pinanediol bromomethaneboronate

: 852509-20-7
(-)-pinanediol (1R,2R)-2-benzyloxy-4-[tert-butoxycarbonyl]-1-chlorobutaneboronate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 75 percent / LDA / tetrahydrofuran; hexane / -78 - 20 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.92 h / -100 °C

2.2: zinc chloride / tetrahydrofuran; hexane; diethyl ether / -100 - 20 °C

3.1: 44 percent / n-butyllithium / tetrahydrofuran; hexane / 2 h / Heating

4.1: n-butyllithium / tetrahydrofuran; hexane / -100 °C

4.2: zinc chloride / tetrahydrofuran; hexane; diethyl ether / -100 - 20 °C

With n-butyllithium; lithium diisopropyl amide; In tetrahydrofuran; hexane;
DOI:10.1016/j.tet.2005.02.069