4291-69-4

Basic information

• Product Name: 2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GALACTOPYRANOSE
• Synonyms: 2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GALACTOPYRANOSE;2,3,4,6-TETRA-O-BENZYL-A-D-GALACTOPYRANOSE, 99% MIN. HPLC;2,3,4,6-TETRA-O-BENZYL-A-D-GALACTOPYRANOSE;2,3,4,5-Tetra- O-benzyl-a-D-galactopyranose;a-D-Galactopyranose, 2,3,4,6-tetrakis-O-(phenylMethyl)-
• CAS NO: 4291-69-4
• Molecular Formula: C₃₄H₃₆O₆
• Molecular Weight: 540.65
• Mol File: 4291-69-4.mol
• Article Data: 162

Chemical Properties

• Melting Point: 152 °C
• Boiling Point: 672.4±55.0 °C(Predicted)
• Appearance: /
• Density: 1.22±0.1 g/cm3(Predicted)
• PKA: 11.87±0.70(Predicted)
• CAS DataBase Reference: 2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GALACTOPYRANOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GALACTOPYRANOSE(4291-69-4)
• EPA Substance Registry System: 2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GALACTOPYRANOSE(4291-69-4)

Safety Data

• Hazardous Substances Data: 4291-69-4(Hazardous Substances Data)

Usage

General Description

2,3,4,6-Tetra-O-benzyl-alpha-D-galactopyranose is a chemical compound that is commonly used as a building block in organic synthesis. It is a derivative of galactose, a type of sugar. 2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GALACTOPYRANOSE is often employed in the production of various pharmaceuticals and other organic molecules due to its ability to be modified and transformed into different structures. The benzyl groups attached to the galactose molecule provide protection and stability, allowing for selective reactions to take place. Overall, 2,3,4,6-Tetra-O-benzyl-alpha-D-galactopyranose is a crucial component in the development of a wide range of organic compounds.

Upstream product

• 13096-63-4 2,3,4,6-Tetra-O-benzyl-N,N-dimethyl-D-gluconamid 
• 6207-45-0 2-(allyloxy)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran 
• 117307-17-2 phenyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside sulfoxide 
• 76670-94-5 2,3,4,6-tetra-O-benzyl-5-dehydro-5-oxo-D-gluconamide 
• 849834-71-5 2-(phenylsulfonyl)ethyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 67-56-1 methanol 
• 56822-48-1 (2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl acetate 
• 50256-33-2 n-pent-4-enyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 84799-77-9 methyl 2,3,4,6-tetra-O-benzyl-D-glucopyranoside 
• 67525-68-2 (2R,3R,4S,5R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-(4-methoxy-phenoxy)-tetrahydro-pyran 
• 131531-76-5 p-methylphenyl 2,3,4,6-tetra-O-benzyl-thio-β-D-glucopyranoside 
• 74808-09-6 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate 
• 28244-94-2 p-tolyl-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 

Downstream Products

• 74024-22-9 2,3:4,5-di-O-isopropylidene-1-O-<2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl>-β-D-fructopyranose 
• 74024-22-9 2,3:4,5-di-O-isopropylidene-1-O-<2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl>-β-D-fructopyranose 
• 3879-79-6 methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 74808-06-3 O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-N,2,2-triphenylacetimidat 
• 74808-05-2 2,3,4,6-tetra-O-benzyl-1-O-(N-4-methylphenyl)diphenylacetimidyl-β-D-glucopyranose 
• 143542-00-1 2-(2,3,4,6-tetra-O-benzyl-D-glycero-D-gulo-hexitol-1-yl)pyrrole 
• 143542-03-4 2,3,4,6-Tetra-O-benzyl-1,1-dipyrryl-1-deoxy-D-glucitol 
• 92414-02-3 2,3,4,6-tetra-O-benzyl-1-O-bromoacetyl-β-D-glucopyranose 
• 129318-98-5 2,3,4,6-tetra-O-benzyl-1-deoxy-1,1-bis(2-hydroxy-4,5-methylenedioxyphenyl)-D-glucitol 
• 74808-15-4 (3aS,4S,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid (2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester 
• 78890-65-0 (3aS,4S,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester 
• 97321-69-2 2,5-anhydro-3,4,7-tri-O-benzyl-1-deoxy-1-phenylseleno-D-glycero-D-gulo-heptitol 
• 97321-68-1 2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-1-phenylseleno-D-glycero-D-ido-heptitol 
• 30608-21-0 1-O-trimethylsilyl-2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 

Relevant articles and documents

Electrochemical Synthesis of Glycosyl Fluorides Using Sulfur(VI) Hexafluoride as the Fluorinating Agent

This manuscript describes the electrochemical synthesis of 17 different glycosyl fluorides in 73-98% yields on up to a 5 g scale that relies on the use of SF6 as an inexpensive and safe fluorinating agent. Cyclic voltammetry and related mechanistic studies carried out subsequently suggest that the active fluorinating species generated through the cathodic reduction of SF6 are transient under these reductive conditions and that the sulfur and fluoride byproducts are effectively scavenged by Zn(II) to generate benign salts.

Design, synthesis, and biological evaluation of desmuramyl dipeptides modified by adamantyl-1,2,3-triazole

Muramyl dipeptide (MDP) is the smallest peptidoglycan fragment able to trigger the immune response. Structural modification of MDP can lead to the preparation of analogs with improved immunostimulant properties, including desmuramyl peptides (DMPs). The aim of this work was to prepare the desmuramyl peptide (L-Ala-D-Glu)-containing adamantyl-triazole moiety and its mannosylated derivative in order to study their immunomodulatory activities in vivo. The adjuvant activity of the prepared compounds was evaluated in a murine model using ovalbumin as an antigen, and compared to the reference adjuvant ManAdDMP. The results showed that the introduction of the lipophilic adamantyl-triazole moiety at the C-terminus of L-Ala-D-Glu contributes to the immunostimulant activity of DMP, and that mannosylation of DMP modified with adamantyl-triazole causes the amplification of its immunostimulant activity.

Discovery of Salidroside-Derivated Glycoside Analogues as Novel Angiogenesis Agents to Treat Diabetic Hind Limb Ischemia

Therapeutic angiogenesis is a potential therapeutic strategy for hind limb ischemia (HLI); however, currently, there are no small-molecule drugs capable of inducing it at the clinical level. Activating the hypoxia-inducible factor-1 (HIF-1) pathway in skeletal muscle induces the secretion of angiogenic factors and thus is an attractive therapeutic angiogenesis strategy. Using salidroside, a natural glycosidic compound as a lead, we performed a structure-activity relationship (SAR) study for developing a more effective and druggable angiogenesis agent. We found a novel glycoside scaffold compound (C-30) with better efficacy than salidroside in enhancing the accumulation of the HIF-1α protein and stimulating the paracrine functions of skeletal muscle cells. This in turn significantly increased the angiogenic potential of vascular endothelial and smooth muscle cells and, subsequently, induced the formation of mature, functional blood vessels in diabetic and nondiabetic HLI mice. Together, this study offers a novel, promising small-molecule-based therapeutic strategy for treating HLI.