166021-01-8

Basic information

• Product Name: 6-O-(TRIISOPROPYLSILYL)-D-GALACTAL
• Synonyms: 6-O-(Triisopropylsilyl)-D-galactal;-2-(((Triisopropylsilyl);-3,4-dihydro-2H-pyran-3,4-diol;oxy);1,5-ANHYDRO-2-DEOXY-6-O-(TRIISOPROPYLSILYL)-D-LYXO-HEX-1-ENITOL;6-O-(TRIISOPROPYLSILYL)-D-GALACTAL
• CAS NO: 166021-01-8
• Molecular Formula: C₁₅H₃₀O₄Si
• Molecular Weight: 336.5
• Product Categories: Monoalkoxysilanes;Si (Classes of Silicon Compounds);Si-O Compounds;Sugars;Biochemistry;Glycals
• Mol File: 166021-01-8.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 361.886°C at 760 mmHg
• Flash Point: 113 °C
• Appearance: /
• Density: 1.016g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: n20/D 1.488(lit.)
• PKA: 12.78±0.60(Predicted)
• CAS DataBase Reference: 6-O-(TRIISOPROPYLSILYL)-D-GALACTAL(CAS DataBase Reference)
• NIST Chemistry Reference: 6-O-(TRIISOPROPYLSILYL)-D-GALACTAL(166021-01-8)
• EPA Substance Registry System: 6-O-(TRIISOPROPYLSILYL)-D-GALACTAL(166021-01-8)

Safety Data

• Hazardous Substances Data: 166021-01-8(Hazardous Substances Data)

Usage

General Description

6-O-(triisopropylsilyl)-D-galactal is a chemical compound that is commonly used as a building block in organic synthesis. It is a derivative of D-galactal, which is a sugar-aldehyde. The "6-O" in its name indicates that the triisopropylsilyl group is attached to the 6th carbon atom of the galactal molecule. This modification can protect the aldehyde functional group from unwanted reactions during chemical transformations, making the compound useful in synthetic chemistry. Additionally, the triisopropylsilyl group can be easily removed under mild conditions to reveal the aldehyde group when desired. Overall, 6-O-(triisopropylsilyl)-D-galactal is a versatile compound that has various applications in organic chemistry.

InChI:InChI=1/C15H30O4Si/c1-10(2)20(11(3)4,12(5)6)19-9-14-15(17)13(16)7-8-18-14/h7-8,10-17H,9H2,1-6H3/t13-,14-,15-/m1/s1

Upstream product

• 4098-06-0 triacetyl-D-galactal 
• 13154-24-0 triisopropylsilyl chloride 
• 21193-75-9 D-galactal 

Downstream Products

• 695177-44-7 Acetic acid (2S,4aR,6R,7R,8S,8aS)-8-acetoxy-6-((2R,3R,4R)-3-hydroxy-2-triisopropylsilanyloxymethyl-3,4-dihydro-2H-pyran-4-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester 
• 695177-43-6 O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->3)-6-O-(triisopropylsilyl)-D-galactal 
• 695177-48-1 O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->3)-6-O-(triisopropylsilyl)-D-galactal 
• 196703-96-5 3,4-di-O-benzyl-6-O-(triisopropylsilyl)-D-galactal 
• 149625-80-9 1,5-anhydro-6-O-triisopropylsilyl-3,4-O-carbonate-2-deoxy-D-lyxo-hex-1-enopyranose 
• 944065-02-5 O-(3,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-2-nitro-α-D-galactopyranosyl)-(1->3)-6-O-(triisopropylsilyl)-D-galactal 
• 944064-87-3 O-(2-azido-2-deoxy-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)(1->3)-6-O-(triisopropylsilyl)-D-galactal 

Relevant articles and documents

Diastereoselective cyclopropanation of electron-deficient alkenes via metal glycal carbenes

Silyl- and isopropylidene-O-protected chromium glucal and galactal carbenes have been synthesized from their glycal precursors according to the Fischer route. NMR studies indicate a preferred 5H4 or 4H5 conformation, depending on the nature of the protective group and the configuration at C-4. The complexes with glycal carbenes have been applied to the diastereoselective cyclopropanation of methyl crotonate and γ-crotonolactone. Georg Thieme Verlag Stuttgart.

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

Cross-coupling reaction of saccharide-based alkenyl boronic acids with aryl halides: The synthesis of bergenin

A convenient synthetic pathway enabling D-glucal and D-galactal pinacol boronates to be prepared in good isolated yields was achieved. Both pinacol boronates were tested in a series of cross-coupling reactions under Suzuki-Miyaura cross-coupling conditions to obtain the corresponding aryl, heteroaryl, and alkenyl derivatives in high isolated yields. This methodology was applied to the formal synthesis of the glucopyranoside moiety of papulacandin D and the first total synthesis of bergenin. Building blocks with boron: A convenient synthetic route to D-glucal and D-galactal pinacol boronates was developed, and the boronates were used in cross-coupling reactions to generate the corresponding aryl, heteroaryl, and alkenyl derivatives in high yields (see scheme). This methodology was applied to the formal synthesis of the glucopyranoside moiety of papulacandin D and the total synthesis of bergenin.