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901237

Sigma-Aldrich

DHR Catalyst

greener alternative

≥95%

Synonym(s):

(2S,3R,4S)-2-Methyltetrahydro-2H-pyran-3,4-diol, Dihydrorhamnal

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About This Item

Empirical Formula (Hill Notation):
C6H12O3
CAS Number:
89614-50-6
Molecular Weight:
132.16
UNSPSC Code:
12352201

assay

≥95%

form

powder or crystals

reaction suitability

reagent type: catalyst

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

greener alternative category

Aligned,

storage temp.

−20°C

SMILES string

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

General description

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.

Application

Dihydrorhamnal (DHR) catalyst was reported by the Morken Lab to be an effective carbohydrate-derived catalyst for enantioselective diboration of alkenes. Related capabilities were observed with the 6-tertbutyldimethylsilyl-1,2-dihydroglucal (TBS-DHG) catalyst( 901235 ).

Other Notes

Related product

Product No.
Description
Pricing

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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Carbohydrate/DBU Cocatalyzed Alkene Diboration: Mechanistic Insight Provides Enhanced Catalytic Efficiency and Substrate Scope
Yan L, et al.
Journal of the American Chemical Society, 140, 3663-3673 (2018)
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.
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.

Related Content

Morken Group – Professor Product Portal

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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