80040-79-5

Basic information

• Product Name: TRI-O-BENZYL-D-GLUCAL
• Synonyms: 3,4,6-TRI-O-BENZYL-D-GALACTAL;1,5-ANHYDRO-3,4,6-TRI-O-BENZYL-2-DEOXY-D-ARABINOHEX-1-ENITOL;1,5-ANHYDRO-2-DEOXY-D-ARABINO-HEX-1-ENITOL 3,4,6-TRIBENZYL ETHER;1,5-ANHYDRO-2-DEOXY-D-LYXO-HEX-1-ENITOL 3,4,6-TRIBENZYL ETHER;TRI-O-BENZYL-D-GLUCAL;TRI-O-BENZYL-D-GALACTAL;3,4,6-Tri-O-benzyl-D-galactal, 98+%;Tri-O-benzyl-D-galactal
• CAS NO: 80040-79-5
• Molecular Formula: C₂₇H₂₈O₄
• Molecular Weight: 416.51
• Product Categories: Biochemistry;Galactose;Glycals;Sugars;Carbohydrate Synthesis;Monosaccharides;Specialty Synthesis;Polysaccharides
• Mol File: 80040-79-5.mol
• Article Data: 56

Chemical Properties

• Melting Point: 57-58 °C(lit.)
• Boiling Point: 544.9 °C at 760 mmHg
• Flash Point: >230 °F
• Appearance: White to Yellow/Powder
• Density: 1.16 g/cm³
• Vapor Pressure: 2.24E-11mmHg at 25°C
• Refractive Index: -34 ° (C=1, MeOH)
• Storage Temp.: −20°C
• Solubility: Soluble in dichloromethane or chloroform,
• CAS DataBase Reference: TRI-O-BENZYL-D-GLUCAL(CAS DataBase Reference)
• NIST Chemistry Reference: TRI-O-BENZYL-D-GLUCAL(80040-79-5)
• EPA Substance Registry System: TRI-O-BENZYL-D-GLUCAL(80040-79-5)

Safety Data

• Safety Statements: S24/25:Avoid contact with skin and eyes.
• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 80040-79-5(Hazardous Substances Data)

Usage

Description

TRI-O-BENZYL-D-GLUCAL is a white to yellowish crystalline powder that serves as an important building block for the synthesis of oligosaccharides through both solution and solid-phase methods.

Uses

Used in Pharmaceutical Industry:
TRI-O-BENZYL-D-GLUCAL is used as a key intermediate in the stereoselective synthesis of various pharmaceutical compounds, such as sphinganine and unnatural safingol. These compounds exhibit antineoplastic and antipsoriatic properties, making them valuable for cancer treatment and addressing skin conditions like psoriasis.
Used in Organic Synthesis:
TRI-O-BENZYL-D-GLUCAL is utilized as a versatile building block in organic synthesis, particularly for the preparation of complex oligosaccharide structures. Its unique structure allows for the selective formation of glycosidic bonds, which is crucial for the development of new pharmaceuticals and bioactive compounds.

InChI:InChI=1/C27H28O4/c1-4-10-22(11-5-1)18-28-21-26-27(31-20-24-14-8-3-9-15-24)25(16-17-29-26)30-19-23-12-6-2-7-13-23/h1-17,25-27H,18-21H2/t25-,26-,27-/m1/s1

Upstream product

• 13265-84-4 1,2-didehydrodideoxyallose 
• 100-39-0 benzyl bromide 
• 125948-55-2 1,5-anhydro-3,6-di-O-acetyl-2-deoxy-D-ribo-hex-1-enitol 
• 52485-06-0 3,4,6-tri-O-acetyl-D-glucal 
• 111425-49-1 phenyl 4,6-di-O-acetyl-2,3-dideoxy-1-thio-α-D-erythro-hex-2-enopyranoside 
• 2873-29-2 D-glucal triacetate 
• 53369-42-9 2,3,4,6-tetra-O-acetyl-α-D-allo-pyranosyl bromide 
• 144071-49-8 1,2,3,4,6-penta-O-acetyl-D-allopyranose 
• 2595-05-3 Diacetone D-glucose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 2847-00-9 1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose 
• 21193-75-9 D-galactal 
• 4098-06-0 triacetyl-D-galactal 
• 100-44-7 benzyl chloride 

Downstream Products

• 124718-61-2 (2R,3R,4R,5S,6S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-5-phenylsulfanyl-tetrahydro-pyran 
• 124718-60-1 (2R,3R,4R,5R,6R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-5-phenylsulfanyl-tetrahydro-pyran 
• 113410-07-4 (2R,3S,4S,5S,6S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-5-phenylsulfanyl-tetrahydro-pyran 
• 113410-05-2 (2R,3S,4S,5R,6R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-5-phenylsulfanyl-tetrahydro-pyran 
• 128358-57-6 3,4,6-tri-O-benzyl-2-deoxy-2-iodo-α-D-talopyranosyl benzenesulfonamide 
• 122194-14-3 2-naphthyl 2-deoxy-2-selenophenyl-3,4,6-tri-O-benzyl-D-galacto-pyranoside 
• 136174-69-1 (2S,3R,4S,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-phenylselanyl-tetrahydro-pyran-2-ol 
• 153808-91-4 Phenyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-1-seleno-α-D-galactopyranoside 
• 113410-06-3 (2R,3S,4S,5R,6S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-5-phenylsulfanyl-tetrahydro-pyran 
• 131326-54-0 O-ethyl S-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl)dithiocarbonate 
• 131326-55-1 O-ethyl S-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranosyl)dithiocarbonate 
• 72605-77-7 (2R,3R,4R)-3,4-bis-benzyloxy-2-benzyloxymethyltetrahydropyran-5-one 
• 137410-20-9 (2E)-4,6-di-O-benzyl-2,3-dideoxy-aldehydo-D-threo-hex-2-enose 
• 94715-75-0 2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranosyl nitrate 

Relevant articles and documents

Iterative Synthesis of 2-Deoxyoligosaccharides Enabled by Stereoselective Visible-Light-Promoted Glycosylation

The photoinitiated intramolecular hydroetherification of alkenols has been used to form C?O bonds, but the intermolecular hydroetherification of alkenes with alcohols remains an unsolved challenge. We herein report the visible-light-promoted 2-deoxyglycosylation of alcohols with glycals. The glycosylation reaction was completed within 2 min in a high quantum yield (?=28.6). This method was suitable for a wide array of substrates and displayed good reaction yields and excellent stereoselectivity. The value of this protocol was further demonstrated by the iterative synthesis of 2-deoxyglycans with α-2-deoxyglycosidic linkages up to a 20-mer in length and digoxin with β-2-deoxyglycosidic linkages. Mechanistic studies indicated that this reaction involved a glycosyl radical cation intermediate and a photoinitiated chain process.

Rhodium-Catalyzed Denitrogenative Transannulation of N-Sulfonyl-1,2,3-triazoles with Glycals Giving Pyrroline-Fused N-Glycosides

Described here is a selective synthesis of 2,3-dihydropyrrole-fused N-glycosides through rhodium-catalyzed denitrogenative transannulation of N-sulfonyl-1,2,3-triazoles with glycals. A series of pyrroline-fused N-glycosides are afforded in moderate to exc

ENGINEERED ANTIBODIES AS MOLECULAR DEGRADERS THROUGH CELLULAR RECEPTORS

The present disclosure provides, in one aspect, bifunctional compounds that can be used to promote or enhance degradation of certain circulating proteins. In certain embodiments, the circulating protein mediates a disease and/or disorder in a subject, and treatment or management of the disease and/or disorder requires degradation, removal, or reduction in concentration of the circulating protein in the subject. Thus, in certain embodiments, administration of a compound of the disclosure to the subject removes or reduces the circulation concentration of the circulating protein, thus treating, ameliorating, or preventing the disease and/or disorder.