59531-24-7

Basic information

• Product Name: (2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)Methyl)tetrahydro-2H-pyran-2-ol
• Synonyms: (2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)Methyl)tetrahydro-2H-pyran-2-ol;EOS-61251
• CAS NO: 59531-24-7
• Molecular Formula: C₃₄H₃₆O₆
• Molecular Weight: 540.64604
• Mol File: 59531-24-7.mol
• Article Data: 171

Chemical Properties

• 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: (2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)Methyl)tetrahydro-2H-pyran-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)Methyl)tetrahydro-2H-pyran-2-ol(59531-24-7)
• EPA Substance Registry System: (2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)Methyl)tetrahydro-2H-pyran-2-ol(59531-24-7)

Safety Data

• Hazardous Substances Data: 59531-24-7(Hazardous Substances Data)

Usage

Description

(2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)Methyl)tetrahydro-2H-pyran-2-ol is a complex organic compound characterized by a tetrahydro-2H-pyran-2-ol core with multiple benzyl ether groups and a (benzyloxy)methyl group attached. This intricate molecular architecture, featuring six benzyl ether groups and the additional (benzyloxy)methyl moiety, indicates potential utility in pharmaceutical development or organic synthesis, where its versatile functional groups can be exploited to achieve specific biological or chemical objectives.

Uses

Used in Pharmaceutical Development:
(2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)Methyl)tetrahydro-2H-pyran-2-ol serves as a key intermediate in the synthesis of pharmaceuticals, leveraging its multiple benzyl ether groups for chemical modifications that can enhance drug properties such as solubility, stability, and bioavailability. (2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)Methyl)tetrahydro-2H-pyran-2-ol's chiral centers also allow for the creation of enantiomers, which may exhibit different pharmacological activities.
Used in Organic Synthesis:
In the field of organic synthesis, (2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)Methyl)tetrahydro-2H-pyran-2-ol is utilized as a versatile building block for the construction of more complex organic molecules. Its benzyl ether groups can be selectively removed or modified, providing a range of synthetic handles for creating diverse chemical entities with potential applications in materials science, agrochemicals, or as precursors to other specialty chemicals.
Used in Drug Delivery Systems:
(2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)Methyl)tetrahydro-2H-pyran-2-ol can be employed in the design of drug delivery systems, where its functional groups can be tailored to improve the encapsulation, targeting, and release of therapeutic agents. (2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)Methyl)tetrahydro-2H-pyran-2-ol's structure may allow for the development of prodrugs or drug conjugates with enhanced pharmacokinetic profiles and reduced side effects.
Used in Chiral Chemistry:
Owing to its multiple chiral centers, (2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)Methyl)tetrahydro-2H-pyran-2-ol is a valuable compound in chiral chemistry. It can be used to study the effects of stereochemistry on biological activity or to develop enantioselective synthetic methods, which are crucial for producing single enantiomers of chiral drugs with improved efficacy and safety profiles.

Upstream product

• 139212-74-1 N-sodio-N'-(2,3,4,6-tetra-O-benzyl-D-glucopyranosylidene)-4-toluenesulfonohydrazidate 
• 150-76-5 4-methoxy-phenol 
• 78890-54-7 1-O-butanoyl-2,3,4,6-tetra-O-benzyl-α-D-glucopyranose 
• 67890-29-3 benzyl 2,3,4,6-tetra-O-benzyl-β-D-gluco-pyranoside 
• 4132-28-9 2,3,4,6-tetra-O-benzyl-D-mannopyranose 
• 90357-89-4 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl trichloroacetimidate 
• 16001-93-7 tetramethyl methylenediphosphonate 
• 4132-28-9 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside 
• 849834-71-5 2-(phenylsulfonyl)ethyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 67-56-1 methanol 
• 642-71-7 3,4,5-trimethoxyphenol 
• 78153-79-4 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl fluoride 
• 87908-21-2 2-methoxyethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 128785-04-6 (2S,3R,4S,5S,6R)-2-[(Dimethyl-phenyl-silanyl)-methoxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 

Downstream Products

• 74808-06-3 O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-N,2,2-triphenylacetimidat 
• 74352-41-3 2-Pyridyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside 
• 144490-57-3 2-pyridyl 2,3,4,6-tetra-O-benzyl-1-thio-αβ-D-glucopyranoside 
• 920749-29-7 Pent-4-enoic acid (3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester 
• 82561-63-5 2,3,4,6-Tetra-O-benzyl-1-O-β-D-glucopyranose 
• 82110-05-2 1,5-di-O-acetyl-2,4,6-tri-O-benzyl-2-dehydro-3-deoxy-D-erythro-hex-2(Z)-enitol 
• 77637-99-1 1,5-di-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucitol 
• 77648-81-8 1,5-di-O-acetyl-2,4,6-tri-O-benzyl-2-dehydro-3-deoxy-D-threo-hex-2-enitol 
• 53929-49-0 Acetic acid (1R,2R,3S,4R)-2,3,4-tris-benzyloxy-1-benzyloxymethyl-5,5-bis-ethylsulfanyl-pentyl ester 
• 77516-85-9 1-O-(2,4-dinitrophenyl)-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 92052-37-4 (2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)acetonitril 
• 92052-36-3 (2,3,4,6-Tetra-O-benzyl-α-D-glucopyranosyl)acetonitril 
• 124813-78-1 methyl 2-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)acetate 
• 140230-23-5 (E)-methyl 4,5,6,8-tetra-O-benzyl-2,3-dideoxy-D-gluco-oct-2-enonate 

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.

Beta-D-glucose short-chain fatty acid ester compound as well as preparation method and application thereof

The invention discloses a beta-D-glucose short-chain fatty acid ester compound as well as a preparation method and application thereof, and belongs to the technical field of organic synthesis. The compound is a compound shown as a formula I, or a stereoisomer, a pharmaceutically acceptable salt, a solvate or a prodrug of the compound shown as the formula I. The formula is as shown in the description, wherein R is a methyl group, an ethyl group, a propyl group, a propylene group, an isopropylidene group, a butyl group, a butylidene group, an isobutylidene group, an amyl group, a pentylidene group or an isoamylidene group. The compound has potential prevention and treatment effects on diabetes, hyperlipidemia, atherosclerosis, Alzheimer's disease, cardiovascular and cerebrovascular diseases,inflammation, tumors and depression.

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.