23558-05-6

Basic information

• Product Name: 3-O-BENZYL-1,2-O-ISOPROPYLIDENE-ALPHA-D-XYLO-PENTODIALDO-1,4-FURANOSE
• Synonyms: 3-O-BENZYL-1,2-O-ISOPROPYLIDENE-ALPHA-D-XYLO-PENTODIALDO-1,4-FURANOSE;3-O-Benzyl-1,2-O-isopropylidene -μ-D-xylo-dialdose;3-O-Benzyl-1,2-O-isopropylidene-a-D-xylo-dialdose;BETA-O-BENZYL-ALPHA,2-O-ISOPROPYLIDINE-ALPHA-D-XYLO-DIALDOSE;3-o-Benzyl-1,2-o-isopropylidene-alpha-D-xylo-dialdose;3-O-Benzyl-1,2-O-isopropylidene-a-D-xylopentodialdo-1,4-furanose;(3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbaldehyde;3-O-Benzyl-1,2-O-isopropylidene-α-D-xylopentodialdo-1,4-furanose
• CAS NO: 23558-05-6
• Molecular Formula: C₁₅H₁₈O₅
• Molecular Weight: 278.3
• Mol File: 23558-05-6.mol
• Article Data: 59

Chemical Properties

• Boiling Point: 379.818°C at 760 mmHg
• Flash Point: 167.107°C
• Appearance: /
• Density: 1.237g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.549
• CAS DataBase Reference: 3-O-BENZYL-1,2-O-ISOPROPYLIDENE-ALPHA-D-XYLO-PENTODIALDO-1,4-FURANOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-O-BENZYL-1,2-O-ISOPROPYLIDENE-ALPHA-D-XYLO-PENTODIALDO-1,4-FURANOSE(23558-05-6)
• EPA Substance Registry System: 3-O-BENZYL-1,2-O-ISOPROPYLIDENE-ALPHA-D-XYLO-PENTODIALDO-1,4-FURANOSE(23558-05-6)

Safety Data

• Hazardous Substances Data: 23558-05-6(Hazardous Substances Data)

Usage

General Description

3-O-Benzyl-1,2-O-isopropylidene-alpha-D-xylo-pentodialdo-1,4-furanose is a chemical compound with the molecular formula C21H24O6. It is a pentodialdose derivative of D-xylose and has a furanose ring structure. 3-O-BENZYL-1,2-O-ISOPROPYLIDENE-ALPHA-D-XYLO-PENTODIALDO-1,4-FURANOSE is commonly used as an intermediate in the synthesis of various pharmaceuticals and organic compounds. It is also known for its potential applications in medicinal chemistry and as a building block for the synthesis of complex molecules. Additionally, it has been studied for its biological activities and potential therapeutic uses.

InChI:InChI=1/C15H18O5/c1-15(2)19-13-12(11(8-16)18-14(13)20-15)17-9-10-6-4-3-5-7-10/h3-8,11-14H,9H2,1-2H3/t11-,12+,13-,14-/m1/s1

Upstream product

• 350255-13-9 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 34370-91-7 3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose 
• 100-39-0 benzyl bromide 
• 101475-83-6 3-O-benzyl-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside 
• 50-99-7 D-glucose 
• 582-52-5 1,2:5,6-diacetone-D-glucose 
• 4205-23-6 D-gulose 
• 308290-81-5 C₁₅H₁₈O₅ 
• 100-44-7 benzyl chloride 
• 14686-89-6 (1,2:5,6)-di-O-isopropylidene-D-gulose 
• 591727-19-4 1-2,5-6 di-O-isopropylidene 3-O-benzyl α(D)gluco-pentoaldofuranose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 42926-89-6 1,2-O-isopropylidene-3-O-benzyl-α-D-glucofuranose 
• 22529-61-9 3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose 

Downstream Products

• 51432-73-6 6t-(1H-benzoimidazol-2-yl)-O³-benzyl-O¹,O²-isopropylidene-α-D-xylo-5,6-dideoxy-hex-5-enofuranose 
• 72671-93-3 (5Ξ)-4t-((3aR)-6c-benzyloxy-2,2-dimethyl-(3ar,6ac)-tetrahydro-furo[2,3-d][1,3]dioxol-5c-yl)-2-oxy-4,5-dihydro-isoxazole-3,5r-dicarboxylic acid dimethyl ester 
• 63522-00-9 2-(3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-tetrofuranos-4-yl)-1,3-dihydroxy-4,4,5,5-tetramethylimidazolidine 
• 51432-68-9 O³-benzyl-O¹,O²-isopropylidene-6c-pyridin-3-yl-α-D-xylo-5,6-dideoxy-hex-5-enofuranose 
• 146176-87-6 (5E,10E,14E,19E)-5,10,15,20-Tetrakis-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-porphyrin 
• 114340-89-5 (S)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-3-hydroxy-propionic acid ethyl ester 
• 162740-21-8 (Z)-N-benzyl-(3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranos-5-ylidene)amine N-oxide 
• 188640-85-9 (R)-1-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-but-3-yn-1-ol 
• 115259-75-1 5-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose 
• 81823-12-3 1,2-O-isopropylidene-3,6-di-O-benzyl-α-D-glucofuranose 
• 906077-01-8 C₁₇H₂₂O₅ 
• 951250-91-2 (-)-(3R,4R,6R,7R,8R)-8-benzyloxy-6,7-O-isopropylidene-2,3-diphenyl-5-oxa-2-aza-spiro[3.4]octan-1-one 

Relevant articles and documents

Method for synthesizing release type xylose ester perfume for tobacco perfuming

A synthesis method of a release type xylose ester spice for flavoring tobacco is provided. The glucose is used as a raw material, the principle of esterifying carboxylic acid and alcohol to prepare ester is adopted, a common parent carboxylic acid which c

Synthesis and Glycosylation Properties of C6-Silylated Ido- and Gluco-Pyranosyl Donors

Silyl groups are widely used as alcohol protecting groups and their study has provided insight on some very remarkable structure and reactivity features within carbohydrate chemistry. However, not much work has been put into the effect on the reactivity of silyl groups directly attached to the sugar carbon chain. In this work, we have developed a synthetic methodology to obtain both d-glucosyl and l-idosyl donors containing a dimethylphenylsilyl group directly attached to C6. Glycosylation and competition experiments with different glycosyl acceptors have shown that this group is completely stable under glycosylation conditions and enhances reactivity beyond what a benzyl group attached to the sugar oxygen would do. Finally, we found adequate conditions for the protodesilylation of Si-containing glycosides to yield the 6-deoxy sugar analog.

N-Alkylated C-Glycosyl Amino Acid Derivatives: Synthesis by a One-Pot Four-Component Ugi Reaction

C-glycosides represent an important group of naturally occurring glycosylation derivatives but are also efficient mimetics of native O-glycosides. Here, a one-pot four-component methodology is described toward a library of N-alkylated C-glycosyl amino acid derivatives comprising seven different isopropylidene-protected carbohydrate units. The applied methodology tolerates different amines and isocyanides and provides access to Ugi products in yields up to 85 %. X-ray analysis of selected products bearing three different carbohydrate motifs and comparison of their crystal structures with similar ones deposited in Cambridge Crystallographic Database revealed that four structures adopt different conformations, mostly not typical for peptide structures. This property opens the possibility to exploit here described N-alkylated C-glycosyl amino acid derivatives as templates to access different biotic and abiotic secondary structures.