335162-25-9

Upstream product

• 7296-64-2 β-D-galactopyranoside 
• 100-51-6 benzyl alcohol 
• 10257-28-0 D-Galactose 

Downstream Products

• 104477-36-3 benzyl 2,3:4,6-bis-O-(1-methylethylidene)-D-galactopyranoside 
• 56341-65-2 Benzyl 4,6-O-benzylidene-β-D-galactopyranoside 
• 57783-86-5 benzyl 4,6-O-benzylidene-α-D-galactopyranoside 
• 217644-10-5 (3aS,4R,7R,7aR)-6-Benzyloxy-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol 
• 86196-36-3 benzyl α-D-galactopyranoside 
• 126900-97-8 benzyl 6-deoxy-3,4-O-isopropylidene-6-phenylthio-α-D-galactopyranoside 
• 217644-09-2 benzyl 2-deoxy-3,4-O-isopropylidene-α-D-lyxohexo-pyranoside 
• 217644-13-8 benzyl 3,4-O-isopropylidene-2-O-<(S-methylthio)-thiocarbonyl>-α-D-galactopyranoside 
• 217644-11-6 3,4-O-isopropylidene-6-S-phenyl-6-thio-α-D-galactopyranoside 
• 10343-13-2 benzyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 
• 142696-63-7 O-benzyl-2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside 
• 39687-22-4 C₅₃H₅₀O₆ 

Relevant academic research and scientific papers

Glycosylated Platinum(IV) Complexes as Substrates for Glucose Transporters (GLUTs) and Organic Cation Transporters (OCTs) Exhibited Cancer Targeting and Human Serum Albumin Binding Properties for Drug Delivery

Glycosylated platinum(IV) complexes were synthesized as substrates for GLUTs and OCTs for the first time, and the cytotoxicity and detailed mechanism were determined in vitro and in vivo. Galactoside Pt(IV), glucoside Pt(IV), and mannoside Pt(IV) were highly cytotoxic and showed specific cancer-targeting properties in vitro and in vivo. Glycosylated platinum(IV) complexes 5, 6, 7, and 8 (IC50 0.24-3.97 μM) had better antitumor activity of nearly 166-fold higher than the positive controls cisplatin (1a), oxaliplatin (3a), and satraplatin (5a). The presence of a hexadecanoic chain allowed binding with human serum albumin (HSA) for drug delivery, which not only enhanced the stability of the inert platinum(IV) prodrugs but also decreased their reduction by reductants present in human whole blood. Their preferential accumulation in cancer cells compared to noncancerous cells (293T and 3T3 cells) suggested that they were potentially safe for clinical therapeutic use.

Direct glycosylation of unprotected and unactivated sugars using bismuth nitrate pentahydrate

Bi(NO3)3, a low-cost, mild, and environmentally green catalyst, has been successfully utilized for Fischer glycosylation for the synthesis of alkyl/aryl glycopyranosides by reacting unprotected sugars, namely, D-glucose, L-rhamnose, D-galactose, D-arabinose, and N-acetyl-D-glucosamine with various alcohols in good to excellent yields. The glycosides were formed with high α-selectivity. Further, an expedient separation of α- and β-glycosides using silver nitrate-impregnated silica gel flash liquid chromatography has been developed.

Montmorillonite K-10 as a reusable catalyst for fischer type of glycosylation under microwave irradiation

Montmorillonite K-10-catalyzed Fischer type glycosylation was studied for various monosacharides with different alcohols under microwave irradiation. The method was found to be efficient, economic, simple, and time saving and the catalyst montmorillonite K-10 was reused three times without loss of catalytic activity and anomeric selectivity. With glycerol, the method gave products glycosylated at primary alcohols only.

Microwave-accelerated Fischer glycosylation

Fischer glycosylation has been used for decades for the synthesis of simple alkyl and aryl glycosides from free sugars. The reaction proceeds under reflux in the presence of catalytic acid with the alcohol as solvent. The main deficiency of this reaction is the long reaction time required. In this study microwave heating has been utilised for the Fischer glycosylation reaction of N-acetyl-d-glucosamine, N-acetyl-d-galactosamine, d-glucose, d-galactose and d-mannose with a variety of alcohols (methanol, ethanol, benzyl alcohol and allyl alcohol). Remarkable acceleration of the glycosylation reactions (minutes compared to hours) over conventional reflux heating was observed with good yields and production of the α-glycoside as the dominant product.

Chemo-enzymatic synthesis of polyhydroxyazepanes

Galactose oxidase (EC 1.1.3.9, GAO) is an extracellular copper-containing enzyme that utilizes molecular oxygen to convert the C6-primary hydroxyl moiety of D-galactopyranosides to hydrated aldehydes. Subsequent dehydratative coupling with hydroxylamines produces oximes (3a-f), which, when subjected to conditions of hydrogenolysis, give rise to polyhydroxyazepanes (11-17).

Practical synthesis of 2,6-dideoxy-D-lyxo-hexose ('2-deoxy-d-fucose') from D-galactose

2,6-Dideoxy-D-lyxo-hexose was prepared efficiently from D-galactose in eight steps (25% overall yield). The synthesis is amenable to multigram scale-up. Copyright (C) 1998 Elsevier Science Ltd.

Synthesis of 5-aminopentyl 4,6-O--β-D-galactopyranoside and its use as a ligand for the affinity chromatography of human serum amyloid P protein

A series of 2,3-di-O-benzoyl-D-galctopyranosides, α-allyl (5), α-benzyl (6), β-ethyl-1-thio (7), β-phenyl-1-thio (8), and α-methyl (9), were prepared from the corresponding 4,6-O-benzylidene derivatives and were acetalated in acetonitrile with methyl pyruvate, to give diastereoselectively the 2,3-di-O-benzoyl-4,6-O--D-galactopyranosides 10-16.The latter were converted into the 2,3-di-O-benzoyl-4,6-O--D-galactopyranosyl α- and β-trichloroacetimidates 19 and 20, α- and β-fluorides 21 and 22, the α-bromide 23, and the α-chloride 24, respectively.These donors, including the phenyl 1-thiogalactoside 14, reacted with 5-pentanol to give the corresponding protected β-D-galactoside 27, deblocking of which afforded the title compound 1.Binding of 1 to epoxypropyl-modified acrylamide beads gave an affinity adsorbent that was used to isolate serum amyloid P protein from human serum.