105928-98-1

Basic information

• Product Name: methyl-2,3,4,6-tetra-O-acetyl-1-thio-α-D-galactopyranoside
• Synonyms: methyl-2,3,4,6-tetra-O-acetyl-1-thio-α-D-galactopyranoside
• CAS NO: 105928-98-1
• Molecular Weight: 378.4
• Mol File: 105928-98-1.mol

Chemical Properties

• CAS DataBase Reference: methyl-2,3,4,6-tetra-O-acetyl-1-thio-α-D-galactopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl-2,3,4,6-tetra-O-acetyl-1-thio-α-D-galactopyranoside(105928-98-1)
• EPA Substance Registry System: methyl-2,3,4,6-tetra-O-acetyl-1-thio-α-D-galactopyranoside(105928-98-1)

Safety Data

• Hazardous Substances Data: 105928-98-1(Hazardous Substances Data)

Upstream product

• 17314-32-8 tributyl(methylthio)stannane 
• 4163-60-4 β-D-galactose peracetate 
• 40591-65-9 Acetic acid (2R,3S,4S,5R)-3,5-diacetoxy-2-acetoxymethyl-6-carbamimidoylsulfanyl-tetrahydro-pyran-4-yl ester; hydrobromide 
• 74-88-4 methyl iodide 
• 3908-55-2 Trimethyl(methylthio)silane 
• 153830-26-3 1,2,3,4,6‐Pentaacetyl α/β‐L‐mannopyranoside 

Downstream Products

• 439-03-2 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl fluoride 
• 115678-25-6 methyl 2-O-<2-O-(2,3,4,6-tetra-O-acetyl-α-L-rhamnopyranosyl)-3,4-di-O-benzyl-α-L-rhamnopyranosyl>-3,4-di-O-benzyl-α-L-rhamnopyranoside 
• 115678-24-5 methyl 2-O-(2,3,4,6-tetra-O-acetyl-α-L-mannopyranosyl)-3,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside 
• 108438-32-0 Methyl 2-O-(α-L-mannopyranosyl)-α-L-rhamnopyranoside 
• 115678-26-7 methyl 2-O(2,3,4,6-tetra-O-acetyl-α-L-rhamnopyranosyl)-3,4-di-O-benzyl-α-L-rhamnopyranoside 

Relevant articles and documents

Synthesis of Oligosaccharides Corresponding to the Common Polysaccharide Antigen of Group B Streptococci

To facilitate mapping of the immunodominant region of the common polysaccharide antigen of group B streptococci, tetrasaccharide 1-O--α-rhamnopyranosyl>-D-glucitol (2) was synthesized in a stepwise fasion

Total synthesis of globotriaosyl-E and Z-ceramides and isoglobotriaosyl-E-ceramide.

Stereoselective, total synthesis of O-alpha-D-galactopyranosyl-(1----4) -O-beta-D-galactopyranosyl-(1----4)-O-beta-D-glucopyranosyl-(1----1)-N -tetracosanoyl-[2S,3R,4E (and 4Z)]-sphingenine and O-alpha-D -galactopyranosyl-(1----3)-O-beta-D-galactopyranosyl-(1----4)-O-beta-D -glucopyranosyl-(1----1)-N-tetracosanoyl-(2S,3R,4E)-sphin gen ine was achieved by using O-(2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl) -(1----4)-O-(2,3,6-tri-O-acetyl-beta-D-galactopyranosyl)-(1----4)-2,3,6- tri-O-acetyl-alpha-D-glucopyranosyl trichloroacetimidate, O-(2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl) -(1----4)-O-(2,3,6-tri-O-acetyl-beta-D-galactopyranosyl)-(1----4)-2,3,6- tri-O-acetyl-alpha (and beta)-D-glucopyranosyl fluoride, and O-(2,3,4,6-tetra-O-acetyl-alpha-D -galactopyranosyl)-(1----3)-O-(2,3,6-tri-O-acetyl-beta-D-galactopyran osyl)-(1----4)-2,3,6-tri-O-acetyl-alpha-D-glucopyranosyl trichloroacetimidate.

LINOMYCIN ANALOGUES. II. CHAIN EXTENSION OF METHYL-6-ALDEHYDO-3,4-O-ISOPROPYLIDENE-1-THIO-β-D-GALACTO-1,5-PYRANOSIDE

Synthesis of methyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-galactopyranoside and its β-anomer (3 and 4) from the 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl bromide via the isothiouronium salt in HMPT involved a considerable increase in the proportion of the α-anomer.Deacetylation of (3 and 4) with sodium methoxide yielded 5 and 6 respectively.Conversion of 6 into corresponding 3,4-isopropylidene derivative (7) followed by oxidation with Collin reagent gave the aldehydo-sugar (8) which when reacted with the stabilized phosphorane led in the excellent yield to the Z-unsaturated bromo-sugar (9).