79999-47-6

Basic information

• Product Name: TRI-O-(TERT-BUTYLDIMETHYLSILYL)-D-GLUCAL
• Synonyms: TRI-O-(TERT-BUTYLDIMETHYLSILYL)-D-GLUCAL;Tri-O-(tert-butyldimethylsilyl)-D-glucal 98%
• CAS NO: 79999-47-6
• Molecular Formula: C₂₄H₅₂O₄Si₃
• Molecular Weight: 504.92
• Product Categories: Carbohydrate Synthesis;Monosaccharides;Specialty Synthesis
• Mol File: 79999-47-6.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 210 °C1.2 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 0.928 g/mL at 25 °C(lit.)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: n20/D 1.456(lit.)
• Sensitive: Air & Moisture Sensitive
• CAS DataBase Reference: TRI-O-(TERT-BUTYLDIMETHYLSILYL)-D-GLUCAL(CAS DataBase Reference)
• NIST Chemistry Reference: TRI-O-(TERT-BUTYLDIMETHYLSILYL)-D-GLUCAL(79999-47-6)
• EPA Substance Registry System: TRI-O-(TERT-BUTYLDIMETHYLSILYL)-D-GLUCAL(79999-47-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 79999-47-6(Hazardous Substances Data)

Usage

General Description

TRI-O-(TERT-BUTYLDIMETHYLSILYL)-D-GLUCAL is a chemical compound that is commonly used as a protective agent for alcohols and as a precursor in organic synthesis. It is a derivative of D-glucal, which is a highly functionalized carbohydrate compound. This specific derivative features three tert-butyldimethylsilyl (TBDMS) groups attached to the hydroxyl groups of the glucal molecule. These TBDMS groups provide protection for the hydroxyl groups during chemical reactions, preventing unwanted side reactions and allowing for selective functionalization of the compound. TRI-O-(TERT-BUTYLDIMETHYLSILYL)-D-GLUCAL is often used in the synthesis of complex organic molecules, particularly in the preparation of natural products and pharmaceuticals.

InChI:InChI=1/C24H52O4Si3/c1-22(2,3)29(10,11)26-18-20-21(28-31(14,15)24(7,8)9)19(16-17-25-20)27-30(12,13)23(4,5)6/h16-17,19-21H,18H2,1-15H3/t19-,20-,21+/m1/s1

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 13265-84-4 D-glucal 
• 2873-29-2 D-glucal triacetate 
• 604-69-3 β-D-glucose pentaacetate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 

Downstream Products

• 105930-88-9 <4aR-(4aα,6α,8α,8aα)>-7,8-Bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-6-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>-4a,7,8,8a-tetrahydro-3-(phenylmethoxy)-1H,6H-pyrano<3,2-e><1,3,4>oxadiazine-1-carboxylic acid phenylmethyl ester 
• 105938-06-5 ((4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-5,6-dihydro-4H-pyran-2-yl)-trimethyl-silane 
• 105938-02-1 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-1-C-methyl-D-arabino-hex-1-enitol 
• 100924-13-8 (1S,3R,4R,5R,6R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-3-(tert-butyl-dimethyl-silanyloxymethyl)-8-(toluene-4-sulfonyl)-2-oxa-8-aza-bicyclo[4.2.0]octan-7-one 
• 240483-07-2 phenyl 3,4,6-tris(O-tert-butyldimethylsilyl)-1-seleno-β-D-glucopyranoside 
• 240483-08-3 phenyl 3,4,6-tris(O-tert-butyldimethylsilyl)-1-seleno-α-D-glucopyranoside 
• 1160754-03-9 C₃₀H₅₇N₃O₄SeSi₃ 
• 1192160-85-2 C₃₀H₅₅NO₆Si₃ 
• 1141254-44-5 C₃₀H₅₆O₄Si₃ 
• 1141254-51-4 C₃₁H₅₈O₄Si₃ 
• 1192160-89-6 C₃₀H₅₅ClO₄Si₃ 
• 1192160-88-5 C₃₀H₅₅BrO₄Si₃ 
• 1141254-46-7 (1S)-1,5-anhydro-2-deoxy-3,4,6-tris-O-[(1,1-dimethylethyl)dimethylsilyl]-1-C-(4-methoxyphenyl)-D-erythro-hex-2-enitol 
• 1141254-49-0 C₃₁H₅₅F₃O₄Si₃ 

Relevant articles and documents

Electrochemical Trifluoromethylation of Glycals

Carbohydrates play essential roles in various physiological and pathological processes. Trifluoromethylated compounds have wide applications in the field of medicinal chemistry. Herein, we report a practical and efficient trifluoromethylation of glycals b

Method for preparing 3,4,6-tri-O-substituent-D-glucal

The invention discloses a method for preparing 3,4,6-tri-O-substituent-D-glucal. The method comprises the following steps: (1) preparation of D-glucal: subjecting 3,4,6-tri-O-acetyl-D-glucal, which serves as a starting raw material, to a reaction under al

A 3,4-trans-fused cyclic protecting group facilitates α-selective catalytic synthesis of 2-deoxyglycosides

A practical approach has been developed to convert glucals and rhamnals into disaccharides or glycoconjugates with high α-selectivity and yields (77-97 %) using a trans-fused cyclic 3,4-O-disiloxane protecting group and TsOH·H2O (1 mol %) as a catalyst. Control of the anomeric selectivity arises from conformational locking of the intermediate oxacarbenium cation. Glucals outperform rhamnals because the C6 side-chain conformation augments the selectivity.