6893-65-8

Basic information

• Product Name: 1,2-O-(1-methylethylidene)-5-O-[(4-methylphenyl)sulfonyl]pentofuranose
• Synonyms: 1,2-O-(1-Methylethylidene)-5-O-[(4-methylphenyl)sulfonyl]pentofuranose
• CAS NO: 6893-65-8
• Molecular Formula: C₁₅H₂₀O₇S
• Molecular Weight: 344.3801
• Mol File: 6893-65-8.mol
• Article Data: 49

Chemical Properties

• Boiling Point: 510.1°C at 760 mmHg
• Flash Point: 262.3°C
• Density: 1.317g/cm³
• Vapor Pressure: 3.14E-11mmHg at 25°C
• Refractive Index: 1.536
• CAS DataBase Reference: 1,2-O-(1-methylethylidene)-5-O-[(4-methylphenyl)sulfonyl]pentofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-O-(1-methylethylidene)-5-O-[(4-methylphenyl)sulfonyl]pentofuranose(6893-65-8)
• EPA Substance Registry System: 1,2-O-(1-methylethylidene)-5-O-[(4-methylphenyl)sulfonyl]pentofuranose(6893-65-8)

Safety Data

• Hazardous Substances Data: 6893-65-8(Hazardous Substances Data)

Usage

Chemical class

Pentofuranoses

Structure

Sulfonyl group attached to the 5-O position
Isopropylidene group at the 1,2-O position

Usage

Protecting group in organic synthesis
Particularly in carbohydrate chemistry

Known for

Stability
Selective protection of hydroxyl groups in sugar molecules during chemical reactions

Application

Synthesis of pharmaceutical intermediates
Synthesis of bioactive compounds

Upstream product

• 5328-37-0 L-arabinose 
• 61329-50-8 O⁵-(toluene-4-sulfonyl)-L-arabinose 
• 67-64-1 acetone 
• 98-59-9 p-toluenesulfonyl chloride 
• 51885-64-4 1,2-O-isopropylidene-β-L-arabinofuranose 
• 1941-50-0 (R)-5,5-Bis-ethylsulfanyl-pentane-1,2,3,4-tetraol 
• 13039-79-7 5-tosyl-L-(+)-arabinose-diethylmercaptal 
• 20031-21-4 1,2-O-isopropylidene-α-D-xylose 
• 58-86-6 D-xylose 
• 20881-04-3 1,2:3,5-di-O-isopropylidene-D-xylofuranose 
• 532-20-7 D-xylofuranose 
• 87-72-9 D-Xylose 
• 532-20-7 α-D-xylofuranose 
• 2460-44-8 β-D-xylopyranoside 

Downstream Products

• 7061-63-4 O¹,O²-isopropylidene-O³,O⁵-bis-(toluene-4-sulfonyl)-β-L-arabinofuranose 
• 6893-78-3 1,2-O-isopropylidene-3-O-methyl-5-O-tosyl-β-L-arabinofuranose 
• 33156-03-5 3-O-acetyl-1,2-O-isopropylidene-5-O-p-toluenesulfonyl-α-D-xylofuranose 
• 69434-49-7 3-O-benzoyl-1,2-O-isopropylidene-5-O-p-toluenesulfonyl-α-D-xylofuranose 
• 17954-92-6 1,2-O-isopropylidene-3-O-methyl-5-O-p-tolylsulfonyl-α-D-xylofuranose 
• 4613-58-5 5-amino-5-deoxy-1,2-O-isopropylidene-a-D-xylofuranose 
• 50600-39-0 5-deoxy-5-iodo-1,2-O-isopropylidene-alpha-D-xylofuranose 
• 77735-29-6 5-S-ethyl-1,2-O-isopropylidene-5-thio-α-D-xylofuranose 
• 65784-67-0 Toluene-4-sulfonic acid (2R,3S,4R)-5,5-bis-benzylselanyl-2,3,4-trihydroxy-pentyl ester 
• 105953-26-2 Toluene-4-sulfonic acid (3aR,5S,6S,6aR)-6-methanesulfonyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester 
• 10548-71-7 5-Desoxy-1,2-O-isopropyliden-5-N-piperidino-D-xylose 
• 124502-76-7 3-(O-tert-butyldimethylsilyl)-5-chloro-1,2-O-isopropylidene-5-S-phenyl-5-thio-α-D-xylofuranose 
• 92413-83-7 3-(O-tert-butyldimethylsilyl)-1,2-O-isopropylidene-5-O-(p-tolylsulfonyl)-α-D-xylofuranose 
• 77988-20-6 1,2-O-isopropylidene-3-O-mesyl-5-O-tosyl-α-D-xylofuranose 

Relevant articles and documents

Control of Crystallinity and Stereocomplexation of Synthetic Carbohydrate Polymers from d- and l-Xylose

Manipulating the stereochemistry of polymers is a powerful method to alter their physical properties. Despite the chirality of monosaccharides, reports on the impact of stereochemistry in natural polysaccharides and synthetic carbohydrate polymers remain absent. Herein, we report the cocrystallisation of regio- and stereoregular polyethers derived from d- and l-xylose, leading to enhanced thermal properties compared to the enantiopure polymers. To the best of our knowledge, this is the first example of a stereocomplex between carbohydrate polymers of opposite chirality. In contrast, atactic polymers obtained from a racemic mixture of monomers are amorphous. We also show that the polymer hydroxyl groups are amenable to post-polymerisation functionalization. These strategies afford a family of carbohydrate polyethers, the physical and chemical properties of which can both be controlled, and which opens new possibilities for polysaccharide mimics in biomedical applications or as advanced materials.

Synthesis and in vitro antitumour activity of 4(R)-methyl-3-O-phosphonomethyl-α-L-threose nucleosides

A series of novel α-L-threose nucleoside phosphonate analogs, 4(R)-methyl-3-O-phosphonomethyl-α-L-threose nucleosides, were synthesized in multistep sequences starting from D-xylose. The synthetic sequence consisted of the following key stages: (i) the multistep synthesis of 1,2-O-isopropylidenyl-4(R)-methyl-3-O-phosphonomethyl-L-threose, (ii) the transformation of 1,2-O-isopropylidenyl sugar into suitable 1,2-di-O-acyl L-threose precursor, and (iii) the construction of target α-L-threose nucleoside phosphonate analogs by Vorbrüggen glycosidation reaction, deprotection of acyl group, and hydrolysis of diethyl group on phosphonate. The target nucleoside phosphonates were evaluated for their antitumour activities in cell culture-based assays. Compound 8g, 2-fluroadenosine phosphonate, showed remarkable activity against human breast cancer cell lines (MCF-7 and MDA-MB-231) with IC50 values of 0.476 and 0.391 μM, corresponding to 41- and 47-fold higher potency than the reference compound 5-FU, respectively. Subsequent investigations found that the compound 8g can inhibit the proliferation of breast cancer cells and cell cloning. The mechanistic studies indicated that compound 8g could cause DNA damage to breast cancer cells through the ATM-Chk1/Chk2-cdc25c pathway, leading to blockage of the G2/M phase cycle of breast cancer cells, which ultimately led to apoptosis. Moreover, 8g could inhibit the PI3K/AKT signaling pathway and induce apoptosis. These results indicate that compound 8g holds promising potential as an antitumour agent.

Synthesis and Antiviral Evaluation of 3'-C-Hydroxymethyl-3'-O-Phosphonomethyl-β-D-5'-deoxyxylose Nucleosides

L-2'-deoxythreose nucleoside phosphonates PMDTA and PMDTT possess potent anti-HIV activity. Herein, a novel class of 3'-C-branched-l-threose nucleoside phosphonate analogs, 5'-deoxy-3'-C-hydroxymethyl-3'-O-phosphonomethyl-d-xylose nucleosides, were synthesized and biologically evaluated. The key sugar intermediate 3-C-benzyloxymethyl-3-O-diethylphosphonomethyl-1,2-O-isopropylidene-α-d-5-deoxyxylose (8) was firstly synthesized, which may be an interesting scaffold for access to diverse 3'-C-branched l-threosyl nucleoside phosphonate derivatives. And the key synthesis involved Wittig olefination of 1,2-O-isopropylidene-3-oxo-α-d-5-deoxyxylose, stereoselective dihydroxylation of alkenes by aqueous KMnO4, selective benzylation of hydroxymethyl group under activation of dibutyltin oxide, and introduction of phosphonate group by nucleophilic substitution. Eventually, glycosylation under Vorbrüggen conditions provided 3'-C-hydroxymethyl-3'-O-phosphonomethyl-β-d-5'-deoxyxylose nucleoside analogs in satisfying yield.