6893-65-8

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

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 
• 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 
• 53458-56-3 S-ethyl-5-thio-L-arabinose 
• 112046-93-2 S-ethyl-L-erythro-5-thio-[2]pentosulose-bis-phenylhydrazone 
• 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 
• 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 

Relevant academic research and scientific papers

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 biological evaluation of benzo[f]indole-4,9-diones n-linked to carbohydrate chains as new type of antitumor agents

In this work, we report the synthesis of three series of carbohydrate-based benzo[f]indole-4,9-diones and amino-1,4-naphthoquinone derivatives and evaluated their cytotoxic activity against eight human cancer cell lines. Several compounds showed a promising cytotoxic activity toward the tumor cell lines (half maximal inhibitory concentration (IC50) 10.0 μM). The importance of the substitution pattern of the quinone derivatives on the antitumor activity was also discussed. 3-Carboethoxy-2-methyl-benzo[f]indole-4,9-dione derivatives were more cytotoxic than their parent compounds and amino-1,4-naphthoquinones. Unlike clinically useful anticancer agent doxorubicin, the majority of synthesized compounds did not exhibit any lytic effects against erythrocytes or normal human leukocytes.

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.

INTERMEDIATE FOR PREPARING ERIBULIN MESYLATE AND PROCESS FOR PREPARING THE SAME

The present invention relates to a process for preparing a compound of formula (6) which is an intermediate for the preparation of eribulin mesylate with high yields and high purity, and an intermediate therefor.

Antitumor (4' R)-methyl - α-L . (by machine translation)

The invention discloses novel α-L - fucosa nucleoside phosphonate analogs, and particularly relates to (4 ′). R- Methyl -3 ' - methyl phosphonic acid - α-L . It has the structure shown in Formula 1. Wherein R ' represents H, Na, K or NH. 4 Ions; B stands for uracil, thymine, 5 - chlorouracil, 5 - fluorouracil, 5 -bromouracil, 5 -fluorouracil, cytosine, 5 - fluorocytosine, adenine, 2 - fluoroadenine, 2 - chloroadenine, 2 - aminoadenine and guanine. The compound has anti-tumor activity and good development prospect. (by machine translation)

Rh-Catalyzed asymmetric hydroaminomethylation of α-Substituted acrylamides: Application in the synthesis of RWAY

The successful rhodium-catalyzed asymmetric hydroformylation and hydroaminomethylation of α-substituted acrylamides is described using 1,3-phosphite-phosphoramidite ligands based on a sugar backbone. A broad scope of chiral aldehydes and amines were afforded in high yields and excellent enantioselectivities (up to 99%). Furthermore, the synthetic potential of this method is demonstrated by the single-step synthesis of the brain imaging molecule RWAY.

Sugar based γ-amino alcohol organocatalyst for asymmetric Michael addition of β-keto esters with nitroolefins

Sugar based γ-amino alcohol was used in asymmetric Michael addition of β-keto esters with nitroolefins for the first time affording the corresponding several chiral Michael adducts bearing quaternary chiral carbon center in moderate to good chemical yields and stereoselectivities (up to 98%, up to dr. 95:5, up to 84% ee).

Molecular Construction of Sulfonamide Antisense Oligonucleotides

An efficient and scalable synthesis of new oligonucleotide monomers was developed for replacement of the phosphodiester backbone of RNA by a sulfonamide-containing backbone to enable construction of sulfonamide antisense oligonucleotides (SaASOs). It was shown that by employing these sulfonamide RNA (SaRNA) monomers, it was possible to synthesize oligomers in solution. The properties of a sulfonamide moiety replacement were evaluated by incorporation of a SaRNA-monomer into a DNA strand and performing thermal stability tests of the resulting DNA and RNA-double-strand hybrids. Although sulfonamide modification caused a decrease in melting temperature (Tm) of both hybrids, it was lower for the sulfonamide-containing DNA-RNA hybrid than that for the sulfonamide-containing DNA-DNA hybrid.

Design, synthesis, cholinesterase inhibition and molecular modelling study of novel tacrine hybrids with carbohydrate derivatives

A series of hybrids containing tacrine linked to carbohydrate-based moieties, such as D-xylose, D-ribose, and D-galactose derivatives, were synthesized by the nucleophilic substitution between 9-aminoalkylamino-1,2,3,4-tetrahydroacridines and the corresponding sugar-based tosylates. All compounds were found to be potent inhibitors of both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) in the nanomolar IC50 scale. Most of the D-xylose derivatives (6a-e) were selective for AChE and the compound 6e (IC50 = 2.2 nM for AChE and 4.93 nM for BuChE) was the most active compound for both enzymes. The D-galactose derivative 8a was the most selective for AChE exhibiting an IC50 ratio of 7.6 for AChE over BuChE. Only two compounds showed a preference for BuChE, namely 7a (D-ribose derivative) and 6b (D-xylose derivative). Molecular docking studies indicated that the inhibitors are capable of interacting with the entire binding cavity and the main contribution of the linker is to enable the most favorable positioning of the two moieties with CAS, PAS, and hydrophobic pocket to provide optimal interactions with the binding cavity. This finding is reinforced by the fact that there is no linear correlation between the linker size and the observed binding affinities. The majority of the new hybrids synthesized in this work do not violate the Lipinski's rule-of-five according to FAF-Drugs4, and do not demonstrated predicted hepatotoxicity according ProTox-II.