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Merck
CN

901235

Sigma-Aldrich

TBS-DHG Catalyst

greener alternative

≥95%

别名:

(2R,3S,4R)-2-(((tert-Butyldimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-3,4-diol, 6-Tertbutyldimethylsilyl-1,2-dihydroglucal

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About This Item

经验公式(希尔记法):
C12H26O4Si
分子量:
262.42
UNSPSC代码:
12352201
NACRES:
NA.22

质量水平

检测方案

≥95%

形式

powder or crystals

反应适用性

reagent type: catalyst

环保替代产品特性

Catalysis
Learn more about the Principles of Green Chemistry.

sustainability

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环保替代产品分类

储存温度

−20°C

SMILES字符串

[H]C1([H])C([H])([H])O[C@@](C([H])([H])O[Si](C([H])([H])[H])(C([H])([H])[H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])([H])[C@](O[H])([H])[C@]1([H])O[H]

一般描述

We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for catalytic efficiency. Click here for more information.

应用

6-Tertbutyldimethylsilyl-1,2-dihydroglucal (TBS-DHG) was reported by the Morken Lab to be an effective carbohydrate-derived catalyst for enantioselective diboration of alkenes. Related capabilities were observed with the dihydrorhamnal (DHR) catalyst (901237). TBS-DHG has also been used in ruthenium(0)catalyzed transfer hydrogenation cycloadditions.

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说明
价格

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

法规信息

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Zachary A Kasun et al.
Chemical communications (Cambridge, England), 50(56), 7545-7547 (2014-06-04)
A new method for the ring expansion of cyclic diols is described. Using improved conditions for the ruthenium(0) catalyzed cycloaddition of cyclic 1,2-diols with 1,3-dienes, fused [n.4.0] bicycles (n = 3-6) are formed, which upon exposure to iodosobenzene diacetate engage
Lichao Fang et al.
Journal of the American Chemical Society, 138(8), 2508-2511 (2016-02-09)
Catalytic enantioselective diboration of alkenes is accomplished with readily available carbohydrate-derived catalysts. Mechanistic experiments suggest the intermediacy of 1,2-bonded diboronates.
Hiroki Sato et al.
Journal of the American Chemical Society, 138(50), 16244-16247 (2016-12-10)
The first use of vicinal diols, ketols, or diones as 2
Lu Yan et al.
Journal of the American Chemical Society, 140(10), 3663-3673 (2018-02-15)
A mechanistic investigation of the carbohydrate/DBU cocatalyzed enantioselective diboration of alkenes is presented. These studies provide an understanding of the origin of stereoselectivity and also reveal a strategy for enhancing reactivity and broadening the substrate scope.

相关内容

Chiral organoboronic esters are well known as versatile intermediates for chemical synthesis. Not only are these compounds stable under a variety of reaction conditions, they are generally non-toxic and can be transformed with minimal generation of hazardous waste.

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