149625-80-9

Basic information

• Product Name: 6-O-(TRIISOPROPYLSILYL)-D-GALACTAL CYCLIC CARBONATE
• Synonyms: 6-O-(TRIISOPROPYLSILYL)-D-GALACTAL CYCLIC CARBONATE;6-O-(triisopropylsilyl)-D-galactal cyclic carbona
• CAS NO: 149625-80-9
• Molecular Formula: C₁₆H₂₈O₅Si
• Molecular Weight: 362.49
• Mol File: 149625-80-9.mol

Chemical Properties

• Melting Point: −52 °C(lit.)
• Boiling Point: 410.3±45.0 °C(Predicted)
• Appearance: /liquid
• Density: 1.087 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.4825(lit.)
• CAS DataBase Reference: 6-O-(TRIISOPROPYLSILYL)-D-GALACTAL CYCLIC CARBONATE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-O-(TRIISOPROPYLSILYL)-D-GALACTAL CYCLIC CARBONATE(149625-80-9)
• EPA Substance Registry System: 6-O-(TRIISOPROPYLSILYL)-D-GALACTAL CYCLIC CARBONATE(149625-80-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 149625-80-9(Hazardous Substances Data)

Upstream product

• 13154-24-0 triisopropylsilyl chloride 
• 21193-75-9 D-galactal 
• 530-62-1 1,1'-carbonyldiimidazole 
• 166021-01-8 1,5-anhydro-6-O-triisopropylsilyl-2-deoxy-D-lyxo-hex-1-enitol 
• 4098-06-0 triacetyl-D-galactal 

Downstream Products

• 162128-74-7 (3aS,4R,6S,7R,7aS)-6-((2R,3S,4R)-4-Benzyloxy-2-benzyloxymethyl-3,4-dihydro-2H-pyran-3-yloxy)-4-triisopropylsilanyloxymethyl-7-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-one 

Relevant articles and documents

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 Asialo GM1. New insights in the application of sulfonamidoglycosylation in oligosaccharide assembly: Subtle proximity effects in the stereochemical governance of glycosidation

The total synthesis of asialo GM1 (1a) has been accomplished. Using related chemistry, the methyl glycoside of the asialo compound (1b) has also been synthesized. These kinds of compounds have been identified as potential ligands for bacterial and viral infection sites. A simpler structure, which has also been identified for its infection attracting structure in the context of glycopeptides and glycolipids (methyl glycoside 2), has also been synthesized. The key common phase in the syntheses involves the sulfonamidoglycosidation reaction which is used to create a β-linkage leading to a ga1NAc residue joined to the C4 hydroxyl group of a galactose unit either as a monosaccharide (see compound 2) or as C4' in the context of a lactosyl moiety. During the course of these studies there was encountered an unusual 'proximal hydroxyl' directing effect. Thus, when C4 on the galactose ring of an azaglycosylating donor bears a free hydroxyl (see, for instance, compound 13), β-glycoside formation predominates. When this hydroxyl group is blocked, the process tends in the direction of α-glycoside formation (see compound 32). These findings were explained as arising from a critical intramolecular hydrogen bond between the C4 axial hydroxyl of the galactose donor and its proximal pyranosidal ring oxygen. This interaction stabilizes conformations from which β-glycosidation predominates.

Total synthesis and proof of structure of a human breast tumor (globo-H) antigen

The total synthesis of the Hakomori MBr1 antigen, heavily expressed on human breast tumors, is related. The construction involved the assembly of four glycals: (17 (twice), 18, 20, and 26) and an L-fucose derivative, 34. The sensitivity of the stereochemi