901235

TBS-DHG Catalyst

≥95%, powder or crystals

• Synonym(s): (2R,3S,4R)-2-(((tert-Butyldimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-3,4-diol, 6-Tertbutyldimethylsilyl-1,2-dihydroglucal
• Empirical Formula (Hill Notation): C₁₂H₂₆O₄Si
• CAS Number: 212120-61-1
• Molecular Weight: 262.42
• MDL number: MFCD31619194
• UNSPSC Code: 12352201
• NACRES: NA.22

Properties

• Product Name: TBS-DHG Catalyst, ≥95%
• InChI: 1S/C12H26O4Si/c1-12(2,3)17(4,5)16-8-10-11(14)9(13)6-7-15-10/h9-11,13-14H,6-8H2,1-5H3/t9-,10-,11+/m1/s1
• InChI key: KKFGQPZYDWCKRC-MXWKQRLJSA-N
• SMILES string: [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]
• 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
• Quality Level: 100

Description

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

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.

Other Notes

• Carbohydrate-Catalyzed Enantioselective Alkene Diboration:Enhanced Reactivity of 1,2-Bonded Diboron Complexes
• Diols, α-Ketols, and Diones as 22π Components in [2+2+2] Cycloadditions of 1,6-Diynes via Ruthenium(0)-Catalyzed Transfer Hydrogenation
• Carbohydrate/DBU Cocatalyzed Alkene Diboration: Mechanistic Insight Provides Enhanced Catalytic Efficiency and Substrate Scope

Safety Information

• wgk: WGK 3
• Storage Class: 11 - Combustible Solids
• flash_point_f: Not applicable
• flash_point_c: Not applicable