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.

TARGETED BIFUNCTIONAL DEGRADERS

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

Azomethine ylide cycloaddition of 2-C-formyl glycals with α-amino acids for the synthesis of substituted pyrroles

A novel strategy has been devised for the synthesis of pyrrole based acyclo-C-nucleosides, in particular an open-chain sugar substituted pyrrole derivatives by means of the condensation of 2-C-formyl glycals with α-amino acids through an intramolecular azomethine cycloaddition under thermal conditions. The use of cyclic α-amino acids provides the corresponding bicyclic pyrrole derivatives. This is a first report on the synthesis of pyrrole based acyclo-C-nucleosides. 2009 Elsevier Ltd. All rights reserved.