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

Chemical Properties

White to yellowish crystalline powder

Uses

Different sources of media describe the Uses of 80040-79-5 differently. You can refer to the following data:
1. An important building block for solution- and solid-phase synthesis of oligosaccharides.
2. Tri-O-benzyl-D-glucal functions as a substance in the stereoselective synthesis of sphinganine and unnatural safingol acting as antineoplastic and antipsoriatic agent for cancer treatment, and affected skin patches.

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

• 153808-91-4 Phenyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-1-seleno-α-D-galactopyranoside 
• 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 
• 113410-06-3 (2R,3S,4S,5R,6S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-5-phenylsulfanyl-tetrahydro-pyran 
• 125710-62-5 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-phenylthio-D-lyxo-hex-1-enitol 
• 164576-05-0 3,4,6-tri-O-benzyl-2-deoxy-α-D-lyxo-hexopyranose 
• 112289-38-0 1,2-anhydro-3,4,6-tri-O-benzyl-D-galactopyranose 
• 149561-64-8 (-)-(2R,3S)-3-(Benzyloxy)-2-<(benzyloxy)methyl>-2,3-dihydro-4H-pyran-4-one 
• 177496-44-5 1-((4aR,6R,7S,8S,8aR)-7,8-Bis-benzyloxy-6-benzyloxymethyl-3-methyl-6,7,8,8a-tetrahydro-4aH-4,5-dioxa-1-thia-naphthalen-2-yl)-ethanone 
• 177570-05-7 (2R,3S,4S,4aR,7S,9aR)-3,4-Bis-benzyloxy-2-benzyloxymethyl-7-methyl-2,3,4a,7,8,9a-hexahydro-4H-1,6,9-trioxa-10-thia-anthracen-5-one 
• 162060-53-9 1,5-anhydro-3,4,6-tri-O-benzyl-D-galactitol 
• 202919-82-2 (2R,3S,4S,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-3-iodotetrahydro-2H-pyran-2-yl acetate 

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.

Ir(I)-Catalyzed C?H Glycosylation for Synthesis of 2-Indolyl-C-Deoxyglycosides

The construction of 2-deoxy-C-glycosides has gradually become a hotspot of carbohydrate chemistry in recent years. In this work, we present an efficient, regioselective, stereoselective and widely applicable strategy for the synthesis of 2-indolyl-C-deoxyglycosides via Ir(I)-catalyzed, pyridine-group-directed C?H functionalization. This method exhibits high tolerance for the functional groups of indoles and the protecting groups of carbohydrates. Moreover, this protocol has good stereoselectivity and mainly produces β-configuration products. Gram-scale synthesis and several practical transformations were conducted for further applications. Meantime, we also explored the mechanism of this method and proposed a catalytic cycle. (Figure presented.).