165524-85-6

Basic information

• Product Name: 6-O-BENZYL-D-GLUCAL,
• Synonyms: (2R,3S,4R)-2-((Benzyloxy)Methyl)-3,4-dihydro-2H-pyran-3,4-diol;1,5-Anhydro-2-deoxy-6-O-(phenylmethyl)-D-arabino-hex-1-enitol
• CAS NO: 165524-85-6
• Molecular Formula: C₁₃H₁₆O₄
• Molecular Weight: 236.27
• Mol File: 165524-85-6.mol

Chemical Properties

• Boiling Point: 384.1 °C at 760 mmHg
• Flash Point: 186.1 °C
• Appearance: /
• Density: 1.247 g/cm³
• Vapor Pressure: 1.38E-06mmHg at 25°C
• Refractive Index: 1.579
• PKA: 12.79±0.60(Predicted)
• CAS DataBase Reference: 6-O-BENZYL-D-GLUCAL,(CAS DataBase Reference)
• NIST Chemistry Reference: 6-O-BENZYL-D-GLUCAL,(165524-85-6)
• EPA Substance Registry System: 6-O-BENZYL-D-GLUCAL,(165524-85-6)

Safety Data

• Safety Statements: S24/25:Avoid contact with skin and eyes.
• Hazardous Substances Data: 165524-85-6(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
6-O-BENZYL-D-GLUCAL is used as a building block in organic synthesis for the creation of complex organic molecules. Its unique structure allows for versatile chemical reactions, facilitating the synthesis of a wide range of compounds.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 6-O-BENZYL-D-GLUCAL is used as a precursor for the synthesis of bioactive molecules. Its potential applications in drug development make it a valuable compound for the design and synthesis of new pharmaceuticals with therapeutic properties.
Used in Drug Development:
6-O-BENZYL-D-GLUCAL is utilized in drug development as a starting material for the creation of novel pharmaceuticals. Its unique chemical properties and potential as a precursor for bioactive molecules contribute to the discovery and development of new drugs with improved efficacy and safety profiles.
Used in Pharmaceutical Industry:
6-O-BENZYL-D-GLUCAL is used as a key intermediate in the pharmaceutical industry for the synthesis of various drugs. Its versatility in organic synthesis and potential as a precursor for bioactive molecules make it an essential component in the development of innovative therapeutic agents.

InChI:InChI=1/C13H16O4/c14-11-6-7-17-12(13(11)15)9-16-8-10-4-2-1-3-5-10/h1-7,11-15H,8-9H2/t11-,12-,13+/m1/s1

Upstream product

• 100-39-0 benzyl bromide 
• 13265-84-4 D-glucal 
• 2873-29-2 D-glucal triacetate 

Downstream Products

• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 165524-88-9 3-O-Acetyl-4,6-di-O-benzyl-D-glucal 
• 165524-87-8 4-O-acetyl-1,5-anhydro-3,6-di-O-benzyl-2-deoxy-D-arabino-hex-1-enitol 
• 202657-32-7 6-O-Benzyl-3-O-triethylsilylglucal 
• 322648-74-8 2,2-Dimethyl-propionic acid (2R,3S,4R)-2-benzyloxymethyl-3-hydroxy-3,4-dihydro-2H-pyran-4-yl ester 
• 825638-49-1 6-O-benzyl-3-deoxy-3-azido-D-gulal 
• 557793-06-3 3-O-(tert-butyldimethylsilyl)-4-O-mesyl-6-O-(benzyl)-D-glucal 
• 322648-62-4 6-O-benzyl-4-O-TES glucal 
• 322648-75-9 2,2-Dimethyl-propionic acid (2R,3S,4R)-2-benzyloxymethyl-3-triethylsilanyloxy-3,4-dihydro-2H-pyran-4-yl ester 
• 322648-63-5 (3aS,4R,6R,7R,7aR)-4-Benzyloxymethyl-6-((2R,3S,4R)-2-benzyloxymethyl-3-triethylsilanyloxy-3,4-dihydro-2H-pyran-4-yloxy)-7-hydroxy-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-one 

Relevant articles and documents

Organoboron-catalyzed regio- and stereoselective formation of β-2-deoxyglycosidic linkages

A borinic acid derived catalyst enables regioselective and β-selective reactions of 2-deoxy- and 2,6-dideoxyglycosyl chloride donors with pyranoside-derived acceptors having unprotected cis-1,2- and 1,3-diol groups. The use of catalysis to promote a β-sel

A 3,4-trans-fused cyclic protecting group facilitates α-selective catalytic synthesis of 2-deoxyglycosides

A practical approach has been developed to convert glucals and rhamnals into disaccharides or glycoconjugates with high α-selectivity and yields (77-97 %) using a trans-fused cyclic 3,4-O-disiloxane protecting group and TsOH·H2O (1 mol %) as a catalyst. Control of the anomeric selectivity arises from conformational locking of the intermediate oxacarbenium cation. Glucals outperform rhamnals because the C6 side-chain conformation augments the selectivity.

Regio- and stereoselectivity of the addition of O-, S-, N-, and C-nucleophiles to the β vinyl oxirane derived from D-glucal

6-O-Trityl- (1a) and 6-(O-benzyl)-substituted epoxide (1b) derived from D-glucal were examined in their addition reactions with O-, C-, N-, and S-nucleophiles. A 1,4-regio- and β-stereoselective or an anti 1,2-addition pathway is commonly observed dependi

New stereoselective β-C-glycosidation by uncatalyzed 1,4-addition of organolithium reagents to a glycal-derived vinyl oxirane

(Matrix presented) Epoxide 4 is generated in situ from D-glucal-derived hydroxy mesylate 3. Reaction of epoxide 4 with a series of alkyl- and aryllithium reagents affords 2,3-unsaturated β-C-glycosides with excellent 1,4-regioselectivity and complete ster

Strategy in oligosaccharide synthesis: An application to a concise total synthesis of the KH-1(adenocarcinoma) Antigen

A concise and potentially practical synthesis of the title compound has been achieved. The route features a high degree of convergence and economy of synthetic operations. A key step is the concurrent introductory addition of three α-1-fucosyl residues at