65190-39-8

Basic information

• Product Name: 1,5-ANHYDRO-4,6-O-BENZYLIDENE-D-GLUCITOL
• Synonyms: 1,5-Anhydro-4,6-O-(phenylmethylene)-D-glucitol;1,5-Anhydro-4,6-O-benzylidene- sorbitol
• CAS NO: 65190-39-8
• Molecular Formula: C₁₃H₁₆O₅
• Molecular Weight: 252.264
• Product Categories: 13C & 2H Sugars;Carbohydrates & Derivatives
• Mol File: 65190-39-8.mol

Chemical Properties

• Melting Point: 160-163°C
• Appearance: /
• Storage Temp.: -20°C Freezer
• CAS DataBase Reference: 1,5-ANHYDRO-4,6-O-BENZYLIDENE-D-GLUCITOL(CAS DataBase Reference)
• NIST Chemistry Reference: 1,5-ANHYDRO-4,6-O-BENZYLIDENE-D-GLUCITOL(65190-39-8)
• EPA Substance Registry System: 1,5-ANHYDRO-4,6-O-BENZYLIDENE-D-GLUCITOL(65190-39-8)

Safety Data

• Hazardous Substances Data: 65190-39-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1,5-Anhydro-4,6-O-benzylidene-D-glucitol is used as a synthetic intermediate for the preparation of sugar nucleotides, which are essential components in various biological processes, including glycosylation, signal transduction, and energy transfer. Its unique structure allows for the development of novel sugar nucleotide analogs with potential applications in the synthesis of complex carbohydrates and glycoconjugates, which are vital for drug discovery and the study of carbohydrate-related diseases.
Used in Chemical Research:
1,5-Anhydro-4,6-O-benzylidene-D-glucitol is also used as a valuable building block in organic synthesis, particularly in the synthesis of complex carbohydrate structures. Its benzylidene protection allows for selective reactions at specific hydroxyl groups, enabling the construction of intricate carbohydrate architectures. This intermediate is useful for researchers in the field of carbohydrate chemistry, providing a versatile platform for the development of new synthetic routes and methodologies.

Upstream product

• 106624-66-2 O¹,O³-((Ξ)-benzyliden)-2,6-anhydro-L-glucitol 
• 897958-85-9 O¹,O³-((Ξ)-benzyliden)-2,6-anhydro-D-glucitol 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 13137-69-4 1-deoxy-D-glucose tetraacetate 
• 154-58-5 1,5-anhydro-D-glucitol 
• 92283-88-0 1,5:2,3-dianhydro-4,6-O-benzylidene-D-allitol 
• 132562-65-3 methyl-(tetra-O-acetyl-α-D-gulopyranoside) 
• 52485-66-2 2,6-anhydro-L-glucitol 
• 17187-64-3 1,3,4,5-tetra-O-benzoyl-β-D-fructopyranosyl bromide 

Downstream Products

• 156715-23-0 1,5-anhydro-4,6-O-benzylidene-2-O-(p-toluoyl)-D-glucitol 
• 66884-53-5 Methanesulfonic acid (R)-7-methanesulfonyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester 
• 161344-98-5 4,5-anhydro-4,6-O-benzylidene-2-(2-amino-6-chloropurin-9-yl)-2,3-dideoxy-D-arabino-hexitol 
• 152613-21-3 1,5-anhydro-4,6-O-benzylidene-2-(adenin-9-yl)-2,3-dideoxy-D-arabino-hexitol 
• 156715-24-1 1,5-anhydro-4,6-O-benzylidene-3-deoxy-2-(p-tolylsulfonyl)-D-ribo-hexitol 
• 152613-23-5 5-Iodo-1-((4aR,7S,8aS)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-1H-pyrimidine-2,4-dione 
• 152614-81-8 5-Methyl-1-((4aR,7S,8aS)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-1H-pyrimidine-2,4-dione 
• 152613-24-6 4-Amino-1-((4aR,7S,8aS)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-1H-pyrimidin-2-one 

Relevant articles and documents

Structure–Activity Relationship Study of a Potent α-Thrombin Binding Aptamer Incorporating Hexitol Nucleotides

The replacement of one or more nucleotide residues in the potent α-thrombin-binding aptamer NU172 with hexitol-based nucleotides has been devised to study the effect of these substitutions on the physicochemical and functional properties of the anticoagulant agent. The incorporation of single hexitol nucleotides at the T9 and G18 positions of NU172 substantially retained the physicochemical features of the parent oligonucleotide, as a result of the biomimetic properties of the hexitol backbone. Importantly, the NU172-TH9 mutant exhibited a higher binding affinity toward human α-thrombin than the native aptamer and an improved stability even after 24 h in 90 percent human serum, with a significant increase in the estimated half-life. The anticoagulant activity of the modified oligonucleotide was also found to be slightly preferable to NU172. Overall, these results confirm the potential of hexitol nucleotides as biomimetic agents, while laying the foundations for the development of NU172-inspired α-thrombin-binding aptamers.

METHOD OF PREPARATION OF NOVEL NUCLEOSIDE ANALOGS AND USES

Processes for the preparation of racemic and optically active nucleoside analogs of formula (A) are described. These compounds are useful as anti-infective agents, antisense therapeutic agents and hybridization assay probes.

1,5-anhydrohexitol nucleoside analogues

1,5-Anhydrohexitol nucleoside analogues represented by the general formula I: STR1 wherein the hexitol has the D-configuration and the carbon atom on which the base moiety and the X substituent stand both have the (S)-configuration and further wherein: B is a heterocyclic ring selected from the group consisting of pyrimidine and purine bases; and X is hydrogen, azido, F, Cl, Br, I, amino, --NHR2, --N(R2)2, --OR2, --SR2, or CN; wherein R1 and R2 are the same or different and are selected from the group consisting of hydrogen, substituted or unsubstituted C1 -C20 alkyl, substituted or unsubstituted C1 -C20 alkenyl, aroyl, C1 -C20 alkanoyl, and phosphoryl. These nucleoside analogues are useful as antiviral agents against herpes simplex virus, vaccina virus, or varicella zoster virus. The definition of the X group should include --N(R2)2 instead of --N(N2)2.

Synthesis and antiherpes virus activity of 1,5-anhydrohexitol nucleosides

The synthesis of 1,5-anhydrohexitol nucleosides is described. These nucleoside analogues were obtained by alkylation of the heterocyclic bases with the tosylate 10 or by alkylation of the bases with the alcohol 12 under Mitsunobu conditions. The compounds were evaluated for antiviral and cytostatic activity. Highly selective activity against herpes simplex virus type 1 (HSV-1) and type 2 (HSV-2) was noted for 1,5-anhydro-2,3-dideoxy-2- (5-iodouracil-1-yl)-D-arabino-hexitol 4b at a concentration of 0.07 μg/mL. This activity must be dependent on a specific phosphorylation by the virus- encoded thymidine kinase (TK), since compound 4b was inactive against TK- deficient mutants of HSV-1. The corresponding cytosine 4c and guanine 4e analogues showed activity against HSV-1, HSV-2, and other herpes viruses (i.e. cytomegalovirus, varicella-zoster virus) at concentrations well below the cytotoxicity threshold (2 and 20 μg/mL, respectively). At these concentrations, compounds 4c and 4e proved also inhibitory to the growth of human T-cells (i.e. MT-4, CEM, MOLT-4).

ANALYSIS BY THE REDUCTIVE-CLEAVAGE METHOD OF LINKAGE POSITIONS IN A POLYSACCHARIDE CONTAINING 4-LINKED D-GLUCOPYRANOSYLURONIC RESIDUES

The fate of 4-linked D-glucopyranosyluronic residues under reductive-cleavage conditions was investigated by using the Klebsiella aerogenes type 54 strain A3 capsular polysaccharide.Treatment of the fully methylated polysaccharide with triethylsilane and