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

Base Information

Chemical Name:(-)-pinanediol (1R,2R)-2-benzyloxy-4-[tert-butoxycarbonyl]-1-vinylbutaneboronate
CAS No.:852509-22-9
Molecular Formula:C₂₈H₄₁BO₅
Molecular Weight:468.442
Hs Code.:

Synonyms:(-)-pinanediol (1R,2R)-2-benzyloxy-4-[tert-butoxycarbonyl]-1-vinylbutaneboronate

Suppliers and Price of (-)-pinanediol (1R,2R)-2-benzyloxy-4-[tert-butoxycarbonyl]-1-vinylbutaneboronate

Supply Marketing:

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

Manufacturers and distributors:

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Chemicals and raw materials
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Total 1 raw suppliers

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

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

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

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

: chloro-methylboronic acid (-)-pinanediolato diester

: 852509-22-9
(-)-pinanediol (1R,2R)-2-benzyloxy-4-[tert-butoxycarbonyl]-1-vinylbutaneboronate

Guidance literature:: Multi-step reaction with 6 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

6.1: 32 percent / tetrahydrofuran / -78 - 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

: 852509-22-9
(-)-pinanediol (1R,2R)-2-benzyloxy-4-[tert-butoxycarbonyl]-1-vinylbutaneboronate

Guidance literature:: Multi-step reaction with 5 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

5.1: 32 percent / tetrahydrofuran / -78 - 20 °C

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

Reference yield:

: 852509-28-5
(3aR,4R,6R,7aS)-2-(iodomethyl)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole

: 852509-22-9
(-)-pinanediol (1R,2R)-2-benzyloxy-4-[tert-butoxycarbonyl]-1-vinylbutaneboronate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 65 percent / LDA / tetrahydrofuran / -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

5.1: 32 percent / tetrahydrofuran / -78 - 20 °C

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