61474-17-7

Basic information

• Product Name: 6-hydroxy-1,2,3,4-tetra-O-acetyl-β-D-galactopyranose
• Synonyms: 6-hydroxy-1,2,3,4-tetra-O-acetyl-β-D-galactopyranose
• CAS NO: 61474-17-7
• Molecular Weight: 348.307
• Mol File: 61474-17-7.mol
• Article Data: 18

Chemical Properties

• CAS DataBase Reference: 6-hydroxy-1,2,3,4-tetra-O-acetyl-β-D-galactopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 6-hydroxy-1,2,3,4-tetra-O-acetyl-β-D-galactopyranose(61474-17-7)
• EPA Substance Registry System: 6-hydroxy-1,2,3,4-tetra-O-acetyl-β-D-galactopyranose(61474-17-7)

Safety Data

• Hazardous Substances Data: 61474-17-7(Hazardous Substances Data)

Upstream product

• 10028-44-1 1,2,3,4-tetra-O-acetyl-6-O-triphenylmethyl-α-D-glucopyranose 
• 604-68-2 α-D-glucopyranose peracetylate 
• 83-87-4 D-glucose pentaacetate 
• 71208-20-3 1,2,3,4-tetra-O-acetyl-6-O-benzoyl-α-D-glucopyranose 
• 4163-60-4 β-D-galactose peracetate 
• 492-62-6 alpha-D-glucopyranose 
• 108-24-7 acetic anhydride 
• 67919-36-2 1,2,3,4-tetra-O-acetyl-6-O-trityl-D-glucopyranoside 
• 54325-28-9 (2R,3R,4S,5S,6R)-6-Trityloxymethyl-tetrahydro-pyran-2,3,4,5-tetraol 
• 54325-28-9 6-O-trityl-α-D-glucose 
• 2280-44-6 D-Glucose 

Downstream Products

• 108257-52-9 1,2,3,4-tetra-O-acetyl-6-O-benzyl-α-D-glucopyranose 
• 98416-49-0 6-O-(bromoacetyl)-1,2,3,4-tetra-O-acetyl-β-D-galactopyranose 
• 71208-20-3 1,2,3,4-tetra-O-acetyl-6-O-benzoyl-α-D-glucopyranose 
• 1034191-98-4 C₂₁H₂₃NO₁₄ 
• 180072-39-3 3,4-di-O-acetyl-6-O-benzoyl-D-glucal 

Relevant articles and documents

Highly efficient deacetylation by use of the neutral organotin catalyst [tBu2SnOH(Cl)]2

Deprotection of acetyl esters is effected cleanly by the neutral organotin catalyst, [tBu2SnOH(Cl)]2. The mildness of the reaction gives rise to great synthetic versatility and in the process a variety of functional groups are tolerated. Differentiations between primary, secondary, and tertiary alcohols and between acetyl ester and other esters are feasible. No racemization occurs with chiral acetyl esters. Exclusive deprotection of primary acetyl esters in carbohydrates and nucleosides is observed. The crude product thus obtained can be used for further reactions without purification.

Diastereoselective Synthesis of Thioglycosides via Pd-Catalyzed Allylic Rearrangement

Stereoselective glycosylation is challenging in carbohydrate chemistry. Herein, stereoselective thioglycosylation of glycals via palladium-catalyzed allylic rearrangement yields various substituents on α-isomer thioglycosides. Two comprehensive series of aryl and benzyl thioglycosides were obtained via a combination of thiosulfates with glycals derived from glucose, arabinose, galactose, and rhamnose. Furthermore, diosgenyl α-l-rhamnoside and isoquercitrin achieved selectivity via stereospecific [2,3]-sigma rearrangements of α-sulfoxide-rhamnoside and α-sulfoxide-glucoside, respectively.

Total synthesis of agalloside, isolated from: Aquilaria agallocha, by the 5-O-glycosylation of flavan

Agalloside (1) is a neural stem cell differentiation activator isolated from Aquilaria agallocha by our group using Hes1 immobilized beads. We conducted the first total synthesis of agalloside (1) via the 5-O-glycosylation of flavan 25 using glycosyl fluoride 20 in the presence of BF3·Et2O. Subsequent oxidation with DDQ to flavanone 2 and deprotection successively provided agalloside (1). This synthetic strategy holds promise for use in the synthesis of 5-O-glycosylated flavonoids. The synthesized agalloside (1) accelerated neural stem cell differentiation, which is a result comparable to that for the naturally occurring compound 1.