4060-34-8

Basic information

• Product Name: 1-chloro-Tri-2,3,5-O-benzyl-D-arabofuranose
• Synonyms: 1-chloro-Tri-2,3,5-O-benzyl-D-arabofuranose
• CAS NO: 4060-34-8
• Molecular Formula: C₂₆H₂₇ClO₄
• Molecular Weight: 438.948
• Mol File: 4060-34-8.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 560.0±50.0 °C(Predicted)
• Appearance: /
• Density: 1.22±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 1-chloro-Tri-2,3,5-O-benzyl-D-arabofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1-chloro-Tri-2,3,5-O-benzyl-D-arabofuranose(4060-34-8)
• EPA Substance Registry System: 1-chloro-Tri-2,3,5-O-benzyl-D-arabofuranose(4060-34-8)

Safety Data

• Hazardous Substances Data: 4060-34-8(Hazardous Substances Data)

Usage

Chemical structure

A complex chemical compound consisting of a D-arabofuranose sugar molecule with chlorination at the 1 position and benzylation at the 2, 3, and 5 positions.

Functional groups

Contains a chloro group (-Cl) at the 1 position and benzyl groups (-CH2Ph) at the 2, 3, and 5 positions.

Stereochemistry

Retains the D-configuration of the arabinose sugar.

Reactivity

The presence of the chloro and benzyl groups makes it a versatile intermediate for the preparation of modified sugars and glycosylation reagents.

Applications

Often used in organic synthesis and medicinal chemistry due to its unique structure and reactivity.

Potential uses

Has potential applications in the development of pharmaceuticals and other biologically active compounds.

Field of interest

Of interest to researchers and scientists working in the field of organic chemistry and drug discovery.

Complexity

Due to its complexity and specific reactivity, it is considered a valuable compound for further research and development.

Upstream product

• 160549-10-0 2,3,5-tri-O-benzyl-D-arabinofuranose 
• 62255-44-1 1-O-acetyl-2,3,5-tris-O-(benzyl)-α, β-D-arabinofuranose 
• 37776-25-3 2,3,5-tri-O-benzyl-D-arabinose 
• 52522-49-3 2,3,5-tri-O-benzyl-1-(4-nitrobenzoyloxy)-D-arabinofuranose 

Downstream Products

• 120288-51-9 1-(2,3,5-Tri-O-benzyl-β-D-arabinofuranosyl)-1,2,4-triazole-3-sulfonamide 
• 76054-98-3 5-amino-4-cyano-1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)imidazole 
• 119368-22-8 1-((2R,3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-1H-pyrazolo[3,4-b]pyridine 
• 84606-41-7 2-(1-isopropylidene)azino-3-(2',3',5'-tri-o-benzyl-α-D-arabinofuranosyl)-5-methoxycarbonylmethylenethiazolidine-4-one 
• 224952-98-1 (2R,3R,4S,5R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-(octyloxy)tetrahydrofuran 
• 326586-22-5 1-allyl-3,4,5-tri-O-benzyl-1-deoxy-β-D-arabinofuranose 
• 326586-21-4 (2R,3R,4R,5R)-2-allyl-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)-tetrahydrofuran 
• 162239-12-5 3,6-anhydro-4,5,7-tri-O-benzyl-1,2-dideoxy-D-gluco-hept-1-enitol 
• 129173-16-6 3,6-anhydro-4,5,7-tri-O-benzyl-1,2-dideoxy-D-manno-hept-1-enitol 
• 115040-65-8 2,3,5-tri-O-benzyl-1-deoxy-1-methyl-β-D-arabinofuranose 
• 115114-57-3 2,3,5-tri-O-benzyl-1-deoxy-1-methyl-α-D-arabinofuranose 
• 143482-59-1 6-azido-2-fluoro-9-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)purine 
• 146-78-1 Fludarabine 
• 113574-99-5 1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)pyrrole-2,4-dicarboxamide 

Relevant articles and documents

Synthesis of an aldosyl chloride by the reaction of thionyl chloride with the 1-O-thallium(I) salt of an aldose

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D-arbinose-based synthesis of homo-C-d4T and homo-C-thymidine

2,3,5-Tri-O-benzyl-D-arabinofuranosyl halides (chloride, bromide) were reacted with AllMgBr, MeMgBr, and VinMgBr to furnish anomeric mixtures of the C-glycosyl products. The factors that influenced the β/α ratio are discussed. The α,β-C-vinyl derivative was transformed into 1-deoxy-1-C-hydroxymethyl-β and α-D-arabinofuranoses (2,5-anhydro-D-glucitol and -mannitol, respectively), separable after isopropylidenation step. 2,5-Anhydro-1,3-O-isopropylidene-D-glucitol was converted into 2,5-anhydro-6-O-triphenylmethyl-D-erythro-hex-3,4-enitol and 2,5-anhydro-4,6-di-O-benzoyl-3-deoxy-D-ribo-hexitol, which were coupled with N-3-benzoylthymine under the Mitsunobu conditions to furnish two analogs of nucleosides with a -CH2- insert between sugar moieties and thymine. (Chemical Equation Presented).

Acceptor-dependent stereoselective glycosylation: 2′-CB glycoside-mediated direct β-D-arabinofuranosylation and efficient synthesis of the octaarabinofuranoside in mycobacterial cell wall

(Chemical Equation Presented) A reliable and generally applicable direct method for the stereoselective β-arabinofuranosylation employing a 2′-carboxybenzyl arabinofuranoside as the glycosyl donor has been established. The acyl-protective group on glycosy