124751-19-5

Basic information

• Product Name: 6-O-(TERT-BUTYLDIMETHYLSILYL)-D-GALACTAL
• Synonyms: 6-O-(TERT-BUTYLDIMETHYLSILYL)-D-GALACTAL;(2R,3R,4R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3,4-dihydro-2H-pyran-3,4-diol
• CAS NO: 124751-19-5
• Molecular Formula: C₁₂H₂₄O₄Si
• Molecular Weight: 260.4
• Product Categories: Carbohydrate Synthesis;Monosaccharides;Specialty Synthesis
• Mol File: 124751-19-5.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 318.8°C at 760 mmHg
• Flash Point: >230 °F
• Appearance: /
• Density: 1.054g/cm³
• Vapor Pressure: 2.92E-05mmHg at 25°C
• Refractive Index: n20/D 1.476(lit.)
• Storage Temp.: ?20°C
• PKA: 12.79±0.60(Predicted)
• CAS DataBase Reference: 6-O-(TERT-BUTYLDIMETHYLSILYL)-D-GALACTAL(CAS DataBase Reference)
• NIST Chemistry Reference: 6-O-(TERT-BUTYLDIMETHYLSILYL)-D-GALACTAL(124751-19-5)
• EPA Substance Registry System: 6-O-(TERT-BUTYLDIMETHYLSILYL)-D-GALACTAL(124751-19-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 124751-19-5(Hazardous Substances Data)

Usage

Uses

Important building block for both solution- and solid-phase synthesis of oligosaccharides.

InChI:InChI=1/C12H24O4Si/c1-12(2,3)17(4,5)16-8-10-11(14)9(13)6-7-15-10/h6-7,9-11,13-14H,8H2,1-5H3/t9-,10-,11-/m1/s1

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 21193-75-9 D-galactal 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 3068-32-4 1-bromo-2,3,4,6-tetra-O-acetyl-D-galactopyranose 
• 4098-06-0 triacetyl-D-galactal 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 25878-60-8 D-galactose pentaacetate 

Downstream Products

• 188010-90-4 1,5-anhydro-6-O-benzyl-3,4-O-carbonate-2-deoxy-D-lyxo-hex-1-enopyranose 
• 149847-26-7 3,4-o-carbonyl-D-galactal 
• 321734-92-3 (2R,3R,4R)-3,4-bis(benzyloxy)-2-(2S,3R,4S,5S,6R)-(((3,4,5-tris-(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)-3,4-dihydro-2H-pyran 
• 1400883-15-9 C₂₁H₃₂O₅Si 
• 136233-14-2 1,5-anhydro-3-O-benzyl-6-O-tert-butyldimetylsilyl-2-deoxy-D-lyxo-hex-1-enopyranose 
• 124581-53-9 (E)-(R)-1-[(2R,3aS,5R,6R,7aS)-6-(4-Bromo-benzyloxy)-2-methoxy-hexahydro-furo[3,2-b]pyran-5-yl]-pent-3-en-2-ol 
• 124581-53-9 (1S,3R,4R,6S,8R)-4-<(4'-bromobenzyl)oxy>-3-<2(S)-hydroxy-3(E)-pentenyl>-8-(methyloxy)-2,7-dioxabicyclo<4.3.0>nonane 

Relevant articles and documents

Stereospecific C-Glycosylation by Mizoroki–Heck Reaction: A Powerful and Easy-to-Set-Up Synthetic Tool to Access α- and β-Aryl-C-Glycosides

A stereospecific Mizoroki–Heck cross-coupling of differently substituted glycals with haloarenes resulting in the exclusive formation of either α- or β-aryl-C-glycosides depending solely on the configuration at C3 was achieved. The reaction was easy to set up because no specific precautions were required concerning moisture or oxygen, and it proceeded by a chirality transfer from C3 to C1. After optimization of cross-coupling conditions, various prepared glycals (7 examples) and arenes (10 examples) were tested, leading stereospecifically to the corresponding aryl-C-glycosides with a carbonyl group at C3, thus opening up new horizons for the total synthesis of glycosylated natural products.

General Strategy for Stereoselective Synthesis of β- N-Glycosyl Sulfonamides via Palladium-Catalyzed Glycosylation

A highly efficient and mild glycosylation reaction between 3,4-O-carbonate glycal and N-tosyl functionalized aliphatic and aromatic amines via palladium-catalyzed decarboxylative allylation is disclosed. A wide range of highly functionalized 2,3-unsaturat

Synthesis of the JKLM-ring fragment of ciguatoxin

A stereoselective synthesis of the LM-ring fragment has been achieved starting from a sugar derivative. A stereoselective synthesis of the JKLM-ring fragment has been achieved through a coupling between two segments via heteroconjugate addition, seven-membered ether ring formation mediated by an acetylene cobalt complex, and spiroketalization reaction.