4132-24-5

Basic information

• Product Name: 1,6-Anhydro-β-D-galactopyranose Triacetate
• Synonyms: 1,6-Anhydro-β-D-galactopyranose Triacetate;2,3,4-Tri-O-acetyl-1,6-anhydro-β-D-galactopyranose
• CAS NO: 4132-24-5
• Molecular Formula: C₁₂H₁₆O₈
• Molecular Weight: 288.25064
• Product Categories: Carbohydrates & Derivatives;Miscellaneous Reagents
• Mol File: 4132-24-5.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• Solubility: Dichloromethane, Ether, Ethyl Acetate
• CAS DataBase Reference: 1,6-Anhydro-β-D-galactopyranose Triacetate(CAS DataBase Reference)
• NIST Chemistry Reference: 1,6-Anhydro-β-D-galactopyranose Triacetate(4132-24-5)
• EPA Substance Registry System: 1,6-Anhydro-β-D-galactopyranose Triacetate(4132-24-5)

Safety Data

• Hazardous Substances Data: 4132-24-5(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Upstream product

• 108-24-7 acetic anhydride 
• 644-76-8 1,6-anhydro-β-D-galactopyranose 
• 67307-86-2 2-O-(benzoyl)-1,6-anhydro-3,4-dideoxy-β-D-erythro-hex-3-enopyranose 
• 121363-55-1 2,3,4-Tri-O-acetyl-6-O-p-toluenesulfonyl-D-galactopyranose 
• 97234-14-5 pentabromophenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 
• 95118-60-8 acetyl 2,3,4-tri-O-acetyl-6-O-tosyl-α/β-D-galactopyranose 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 4163-60-4 β-D-galactose peracetate 
• 81969-64-4 1,6-Anhydro-α-L-idohexofuranose 

Downstream Products

• 644-76-8 1,6-anhydro-β-D-galactopyranose 

Relevant articles and documents

1,6-Anhydro-1-thio-β-D-glucopyranose (thiolevoglucosan) and the corresponding sulfoxides and sulfone

Starting 1,2,3,4-tetra-O-acetyl-6-O-tosyl-β-D-glucopyranose (3) was converted into 2,3,4-tri-O-acetyl-1-thio-6-O-tosyl-β-D-glucopyranose (6) via intermediate glycosyl bromide 4 and S-thiouronium salt 5. Treatment of compound 6 with sodium methoxide gave 1,6-anhydro-1-thio-β-D-glucopyranose (thiolevoglucosan 2a). The isomeric sulfoxides 7 and 8 were prepared by selective oxidation of thiolevoglucosan 2a with hydrogen peroxide or 3-chloroperoxybenzoic acid. The structure of new compounds was confirmed by 1H and 13C NMR spectroscopy or by X-ray analysis; magnetic anisotropy of the sulfinyl and sulfonyl group has been discussed.

Method of preparing levoglucosenone

Levoglucosenone is prepared by reaction sequence using 1,6-anhydro-β-D-galactopyranose as a starting material. First, the starting material is reacted with ortho formate, obtaining an ortho ester of said starting material. Then, the ortho ester is placed under the conditions for a reductive elimination reaction of the ortho formate part of said ortho ester, thereby converting said ortho ester to a 1,6-anhydro-3,4-dideoxy derivative. The dideoxy derivative is placed under the conditions for oxidation of the hydroxy group of said dideoxy derivative, thereby forming levoglucosenone.

Synthesis of Levoglucosenone

Levoglucosenone was synthesized from D-galactose via reductive decarboxylation as a key reaction.Among the catalysts used for the key reaction, hydrous zirconium oxide was found to have the best activity.