19186-40-4

Basic information

• Product Name: 1,3,4,6-TETRA-O-ACETYL-ALPHA-D-GALACTOPYRANOSE
• Synonyms: 1,3,4,6-TETRA-O-ACETYL-A-D-GALACTOPYRANOSE;1,3,4,6-TETRA-O-ACETYL-ALPHA-D-GALACTOPYRANOSE;2,3,4,6-TETRA-O-ACETYL A-D-GALACTOPYRANOSIDE;α-D-Galactopyranose 1,3,4,6-Tetraacetate
• CAS NO: 19186-40-4
• Molecular Formula: C₁₄H₂₀O₁₀
• Molecular Weight: 348.3
• Product Categories: Carbohydrates & Derivatives
• Mol File: 19186-40-4.mol
• Article Data: 7

Chemical Properties

• Melting Point: 138-140°C
• Boiling Point: 160-170 °C(Press: 0.01 Torr)
• Appearance: /
• Density: 1.33±0.1 g/cm3(Predicted)
• Refractive Index: 1.492
• PKA: 12.22±0.70(Predicted)
• CAS DataBase Reference: 1,3,4,6-TETRA-O-ACETYL-ALPHA-D-GALACTOPYRANOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,4,6-TETRA-O-ACETYL-ALPHA-D-GALACTOPYRANOSE(19186-40-4)
• EPA Substance Registry System: 1,3,4,6-TETRA-O-ACETYL-ALPHA-D-GALACTOPYRANOSE(19186-40-4)

Safety Data

• Hazardous Substances Data: 19186-40-4(Hazardous Substances Data)

Usage

Description

1,3,4,6-TETRA-O-ACETYL-ALPHA-D-GALACTOPYRANOSE is a complex carbohydrate derivative with the chemical formula C18H24O12. It is an off-white solid and is a key intermediate in the synthesis of various biologically active compounds, particularly in the field of carbohydrate chemistry.

Uses

Used in Pharmaceutical Industry:
1,3,4,6-TETRA-O-ACETYL-ALPHA-D-GALACTOPYRANOSE is used as a key intermediate in the preparation and synthesis of galacturonic acid containing pentasaccharide antigen. This pentasaccharide antigen plays a crucial role in the development of vaccines and therapeutic agents targeting specific diseases.
Used in Carbohydrate Chemistry Research:
1,3,4,6-TETRA-O-ACETYL-ALPHA-D-GALACTOPYRANOSE is used as a starting material for the synthesis of various complex carbohydrates and their derivatives. These synthesized compounds can be employed in the development of new drugs, biomaterials, and other applications in the field of biotechnology and pharmaceuticals.
Used in Material Science:
1,3,4,6-TETRA-O-ACETYL-ALPHA-D-GALACTOPYRANOSE can be utilized in the development of novel materials with specific properties, such as improved biocompatibility, enhanced stability, or targeted drug delivery capabilities. These materials can be applied in various industries, including medical, pharmaceutical, and environmental sectors.

InChI:InChI=1/C14H20O10/c1-6(15)20-5-10-12(21-7(2)16)13(22-8(3)17)11(19)14(24-10)23-9(4)18/h10-14,19H,5H2,1-4H3/t10?,11-,12-,13+,14-/m0/s1

Upstream product

• 59-23-4 D-Galactose 
• 108-24-7 acetic anhydride 
• 572-10-1 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl chloride 
• 3254-15-7 3,4,6-tri-O-acetyl-1,2-O-(1-ethoxyethylidene)-α-D-galactopyranose 
• 4163-60-4 β-D-galactose peracetate 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 192753-82-5 2-O-benzyl-3,4,5,6-di-O-isopropyliclenealdehydo-L-gulose 

Downstream Products

• 139760-07-9 O-(2,3,4-Tri-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-1,3,4,6-tetra-O-acetyl-α-D-galactopyranose 
• 130052-61-8 1,3,4,6-tetra-O-acetyl-2-O-trityl-α-D-galactopyranose 
• 151475-03-5 1,3,4,6-Tetra-O-acetyl-2-O-(4-cyanobenzoyl)-α-D-glucopyranose 
• 151475-02-4 1,3,4,6-Tetra-O-acetyl-2-O-(3,4,5-trimethoxybenzoyl)-α-D-glucopyranose 
• 117991-67-0 1,3,4,6-tetra-O-acetyl-2-O-benzoyl-α-D-galactopyranose 
• 117991-68-1 1,3,4,6-Tetra-O-acetyl-2-O-(p-methoxybenzoyl)-α-D-glucopyranose 
• 139760-12-6 C₆₁H₆₀O₂₃ 
• 117991-69-2 1,3,4,6-Tetra-O-acetyl-2-O-(p-bromobenzoyl)-α-D-glucopyranose 
• 21232-74-6 1,3,4,6-Tetra-O-acetyl-2-O-(diphenoxyphosphoryl)-α-D-galactopyranose 
• 163152-12-3 1,3,4,6-tetra-O-acetyl-2-O-<2-(chloroacetoxymethyl)benzoyl>-α-D-galactopyranose 
• 93495-93-3 1,3,4,6-tetra-O-acetyl-2-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-α-D-galactopyranose 
• 93495-92-2 1,3,4,6-tetra-O-acetyl-2-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-α-D-galactopyranose 
• 385422-27-5 1,3,4,6-tetra-O-acetyl-2-O-(2-(azidomethyl)benzoyl)-α-D-galactopyranoside 
• 865860-12-4 acetyl 3,4,6-tri-O-acetyl-2-O-{(1S)-phenyl-2-(phenylsulfanyl)ethyl}-α-D-galactopyranose 

Relevant articles and documents

Convenient synthesis of D-talose from D-galactose

The rare and expensive D-talose was conveniently synthesized from readily available D-galactose in four steps with an overall yield of 58%. The key step was the inversion of equatorial 2-OH of galactose to the axial one by S N2 reaction under the modified Lattrell-Dax reaction conditions.

SYNTHESIS AND USE OF GLYCODENDRIMER REAGENTS

The present invention relates to a chemically modified mutant protein including a cysteine residue substituted for a residue other than cysteine n a precursor protein, the substituted cysteine residue being subsequently modified by reacting the cysteine residue with a glycosylated thiosulfonate. Also a method of producing the chemically modified mutant protein is provided. The present invention also relates to a glycosylated methanethiosulfonate. Another aspect of the present invention is a method of modifying the functional characteristics of a protein including providing a protein and reacting the protein with a glycosylated methanethiosulfonate reagent under conditions effective to produce a glycoprotein with altered functional characteristics as compared to the protein. In addition, the present invention relates to methods of determining the structure-function relationships of chemically modified mutant proteins. The present invention also relates to synthetic methods for producing thio-glycoses, the thio-glycoses so produced, and to methods for producing glycodendrimer reagents.

Carbohydrate Homologation by the Use of 2-(Trimethylsilyl)thiazole. Preparative Scale Synthesis of Rare Sugars: L-Gulose, L-Idose, and the Disaccharide Subunit of Bleomycin A2

The well established one-carbon homologation method of protected monosaccharides employing 2-(trimethylsilyl)thiazole (2-TST) as a formyl anion equivalent has been used for high yield and multigram scale synthesis of the title rare hexoses from L-xylose. Thus, L-gulose has been obtained by stereoselective anti-addition of 2-TST to aldehydo-L-xylose diacetonide followed by thiazole to formyl conversion of the resulting alcohol. The inversion of configuration at C-1 of this alcohol by an oxidation - reduction sequence prior to the aldehyde releasing from thiazole led to L-idose. The same alcohol was readily elaborated into 1,3,4,6-tetra-O-acetyl-L-gulopyranose whose highly stereoselective glycosidation coupling with 3-O-carbamoyl-2,4,6-tri-O-acetyl-α-D-mannosyl diethyl phosphate afforded the same peracetylated disaccharide subunit employed by Boger and Honda in the total synthesis of the antibiotic bleomycin A2.