(1S,2S,3R,5S)-pinanediol (1S,2S)-[2-benzyloxy-3-(tert-butyldimethylsilyloxy)-1-(2-oxyethyl)-propyl]boronate

Base Information

Chemical Name:(1S,2S,3R,5S)-pinanediol (1S,2S)-[2-benzyloxy-3-(tert-butyldimethylsilyloxy)-1-(2-oxyethyl)-propyl]boronate
CAS No.:1415692-97-5
Molecular Formula:C₂₈H₄₅BO₅Si
Molecular Weight:500.559
Hs Code.:

Synonyms:(1S,2S,3R,5S)-pinanediol (1S,2S)-[2-benzyloxy-3-(tert-butyldimethylsilyloxy)-1-(2-oxyethyl)-propyl]boronate

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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 (1S,2S,3R,5S)-pinanediol (1S,2S)-[2-benzyloxy-3-(tert-butyldimethylsilyloxy)-1-(2-oxyethyl)-propyl]boronate

Chemical Property:

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Technology Process of (1S,2S,3R,5S)-pinanediol (1S,2S)-[2-benzyloxy-3-(tert-butyldimethylsilyloxy)-1-(2-oxyethyl)-propyl]boronate

There total 6 articles about (1S,2S,3R,5S)-pinanediol (1S,2S)-[2-benzyloxy-3-(tert-butyldimethylsilyloxy)-1-(2-oxyethyl)-propyl]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: 63.0%

: 1415692-96-4
(1S,2S,3R,5S)-pinanediol (1S,2S)-[1-allyl-2-benzyloxy-3-(t-butyldimethylsilyloxy)propyl]boronate

: 1415692-97-5
(1S,2S,3R,5S)-pinanediol (1S,2S)-[2-benzyloxy-3-(tert-butyldimethylsilyloxy)-1-(2-oxyethyl)-propyl]boronate

Guidance literature:: With 2,6-dimethylpyridine; sodium periodate; potassium osmate(VI) dihydrate; In 1,4-dioxane; water; at 20 ℃;
DOI:10.1039/c2ob26756j

Reference yield:

: 304915-07-9
[2(1R),4S,5S]-4,5-dicyclohexyl-2-[1-chloro-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-1,3,2-dioxaborolane

: 1415692-97-5
(1S,2S,3R,5S)-pinanediol (1S,2S)-[2-benzyloxy-3-(tert-butyldimethylsilyloxy)-1-(2-oxyethyl)-propyl]boronate

Guidance literature:: Multi-step reaction with 5 steps

1: sodium hydride / tetrahydrofuran; mineral oil / Reflux

2: diethyl ether; water

3: zinc(II) chloride; lithium diisopropyl amide / tetrahydrofuran

4: tetrahydrofuran

5: potassium osmate(VI) dihydrate; sodium periodate; 2,6-dimethylpyridine / water; 1,4-dioxane / 20 °C

With 2,6-dimethylpyridine; sodium periodate; potassium osmate(VI) dihydrate; sodium hydride; zinc(II) chloride; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; diethyl ether; water; mineral oil;
DOI:10.1039/c2ob26756j

Reference yield:

: 304915-06-8
(4S,5S)-4,5-dicyclohexyl-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl-1,3,2-dioxaborolane

: 1415692-97-5
(1S,2S,3R,5S)-pinanediol (1S,2S)-[2-benzyloxy-3-(tert-butyldimethylsilyloxy)-1-(2-oxyethyl)-propyl]boronate

Guidance literature:: Multi-step reaction with 6 steps

1: zinc(II) chloride; n-butyllithium; dichloromethane / hexane; tetrahydrofuran; diethyl ether / 20 °C

2: sodium hydride / tetrahydrofuran; mineral oil / Reflux

3: diethyl ether; water

4: zinc(II) chloride; lithium diisopropyl amide / tetrahydrofuran

5: tetrahydrofuran

6: potassium osmate(VI) dihydrate; sodium periodate; 2,6-dimethylpyridine / water; 1,4-dioxane / 20 °C

With 2,6-dimethylpyridine; sodium periodate; n-butyllithium; dichloromethane; potassium osmate(VI) dihydrate; sodium hydride; zinc(II) chloride; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; diethyl ether; hexane; water; mineral oil;
DOI:10.1039/c2ob26756j