5329-50-0

Basic information

• Product Name: BENZYL-BETA-L-ARABINOPYRANOSIDE
• Synonyms: Benzylb-L-arabinopyranoside;Benzyl pentopyranoside;Nsc2561;(2R,3S,4R,5R)-2-(Benzyloxy)Tetrahydro-2H-Pyran-3,4,5-Triol;(2R,3S,4R,5R)-2-(Benzyloxy)Tetrahydro-2H-Pyran-3,4,5-Triol(WXC04258)
• CAS NO: 5329-50-0
• Molecular Formula: C₁₂H₁₆O₅
• Molecular Weight: 240.25
• Product Categories: Carbohydrates & Derivatives
• Mol File: 5329-50-0.mol
• Article Data: 9

Chemical Properties

• Melting Point: 169-173°C
• Boiling Point: 418.5°Cat760mmHg
• Flash Point: 206.9°C
• Appearance: /
• Density: 1.35g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.597
• Storage Temp.: Refrigerator
• Solubility: DMSO, Methanol, Water
• CAS DataBase Reference: BENZYL-BETA-L-ARABINOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZYL-BETA-L-ARABINOPYRANOSIDE(5329-50-0)
• EPA Substance Registry System: BENZYL-BETA-L-ARABINOPYRANOSIDE(5329-50-0)

Safety Data

• Hazardous Substances Data: 5329-50-0(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

InChI:InChI=1/C12H16O5/c13-9-7-17-12(11(15)10(9)14)16-6-8-4-2-1-3-5-8/h1-5,9-15H,6-7H2/t9-,10+,11?,12-/m1/s1

Upstream product

• 87-72-9 L-arabinofuranose 
• 100-51-6 benzyl alcohol 
• 5328-37-0 L-arabinose 
• 1114-34-7 D-lyxose 
• 28697-53-2 D-arabinopyranose 
• 87-72-9 (-)-D-arabinose 
• 10323-20-3 D-Arabinose 
• 391928-90-8 (2S)-2-benzyloxy-2H-pyran-3-(6H)-one 
• 14125-76-9 1,5-anhydro-2,3,4-tri-O-acetyl-D-threo-pent-1-enitol 
• 62446-93-9 1,2,3,4-tetra-O-acetyl-D-xylopyranose 
• 87-72-9 D-Xylose 
• 391928-94-2 benzyl 3,4-dideoxy-α-L-glycero-pent-3-enopyranoside 

Downstream Products

• 103773-81-5 1-O-benzyl-2,3-isopropylidene-L-lyxopyranose 
• 1015076-56-8 benzyl 4-O-acetyl-β-D-arabinopyranoside 
• 67412-71-9 (-)-benzyl 2,3-anhydro-β-D-ribopyranoside 
• 7143-64-8 (-)-benzyl 2-O-methanesulfonyl-β-D-arabinopyranoside 
• 97989-81-6 (-)-benzyl β-D-gentosaminide 
• 120041-97-6 (-)-benzyl 3-deoxy-3-(N-methoxycarbonyl-N-methylamino)-β-D-xylopyranoside 
• 120041-98-7 (-)-benzyl 3-deoxy-2,4-bis-(O-methoxymethyl)-3-(N-methoxycarbonyl-N-methylamino)-β-D-xylopyranoside 
• 120042-03-7 (2R,3R,4R,5S,6RS)-2-(2,5-dibenzyloxy-3,4-dimethylphenyl)-6-hydroxy-4-(N-methoxycarbonyl-N-methylamino)-3,5-bis(methoxymethyloxy)-2-methyltetrahydropyran 
• 120042-03-7 (2S,3R,4R,5S,6RS)-2-(2,5-dibenzyloxy-3,4-dimethylphenyl)-6-hydroxy-4-(N-methoxycarbonyl-N-methylamino)-3,5-bis(methoxymethyloxy)-2-methyltetrahydropyran 
• 97989-87-2 (2S,3R,4S,5S)-(-)-2-(2,5-dibenzyloxy-3,4-dimethylphenyl)-6-(tert-butyldimethylsilyloxy)-4-(N-methoxycarbonyl-N-methylamino)-2,4-bis(methoxymethyloxy)-2-hexanol 
• 97989-87-2 (2R,3R,4S,5S)-(-)-2-(2,5-dibenzyloxy-3,4-dimethylphenyl)-6-(tert-butyldimethylsilyloxy)-4-(N-methoxycarbonyl-N-methylamino)-2,4-bis(methoxymethyloxy)-2-hexanol 
• 97989-89-4 (2R,3S,4R,5R)-(-)-5-(2,5-dibenzyloxy-3,4-dimethylphenyl)-3-(N-methoxycarbonyl-N-methylamino)-2,4-bis(methoxymethyloxy)-1,5-hexanediol 
• 97989-89-4 (2S,3S,4R,5S)-(+)-5-(2,5-dibenzyloxy-3,4-dimethylphenyl)-3-(N-methoxycarbonyl-N-methylamino)-2,4-bis(methoxymethyloxy)-1,5-hexanediol 
• 120041-96-5 benzyl 3,4-O-isopropylidene-2-O-methanesulfonyl-β-D-arabinopyranoside 

Relevant articles and documents

A Click-Chemistry Linked 2′3′-cGAMP Analogue

2′3′-cGAMP is an uncanonical cyclic dinucleotide where one A and one G base are connected via a 3′-5′ and a unique 2′-5′ linkage. The molecule is produced by the cyclase cGAS in response to cytosolic DNA binding. cGAMP activates STING and hence one of the most powerful pathways of innate immunity. cGAMP analogues with uncharged linkages that feature better cellular penetrability are currently highly desired. Here, the synthesis of a cGAMP analogue with one amide and one triazole linkage is reported. The molecule is best prepared via a first CuI-catalyzed click reaction, which establishes the triazole, while the cyclization is achieved by macrolactamization.

NEW METHOD FOR PREPARING ISOFAGOMINE AND ITS DERIVATIVES

A method for preparing isofagomine, its derivatives, intermediates and salts thereof using novel processes to make isofagomine from D-(-)-arabinose and L-(-)-xylose.

Synthesis of optically active 2-alkoxy-2H-pyran-3(6H)-ones. Their use as dienophiles in Diels-Alder cycloadditions

Optically active 2-alkoxy-2H-pyran-3(6H)-ones (4a-d) were synthesized in one step by the tin(IV) chloride-promoted glycosylation and rearrangement of the 2-acetoxy-3,4-di-O-acetyl-D-xylal (3) prepared from D-xylose (1). The absolute configuration of the new stereocenter at C-2 was determined by chemical transformation of the dihydropyranones 4a and 4b into the known alkyl pentopyranosides (7a and 7b, respectively). Also, from 1H NMR experiments using a chiral ytterbium shift reagent, the enantiomeric excesses for 4a (> 86%) and 4b (>77%) were established. Enantiomerically pure 4c and 4d were obtained by reaction of 3 with chiral 2-octanol (R and S, respectively). Dihydropyranones 4a-d were employed as dienophiles in Diels-Alder cycloadditions with 2,3-dimethylbutadiene and butadiene. Under thermal conditions, only moderate yields (～50%) of cycloadducts 9a-c and 10a were respectively obtained with good diastereofacial selectivity (> 80%). Optimized Lewis acid promoted cycloadditions led to 9a-d and 10a,c in higher yields (～80%) and with higher diastereoselectivities (> 94%). The major products were formed by approach of the dienes from the less hindered face of the dihydropyranones, and the minor products (such as 11a) were formed by addition from the opposite side. Furthermore, cycloadduct 9a was stable in an alkaline solution, whereas 11a underwent epimerization under the same conditions.