596103-06-9

Usage

Chemical family

Ribitols, which are sugar alcohols.

Presence of functional groups

Thiol group (sulfhydryl group) and isopropylidene group.

Isopropylidene group function

Protective group used in organic synthesis.

Potential applications

Organic chemistry, pharmaceuticals, and biochemistry research.

Use as a building block

Synthesis of more complex molecules.

Use as a reagent

Various chemical reactions.

Unique chemical properties

Imparted by the thiol group, useful in specific chemical processes.

Diverse potential uses

Different fields of science and industry.

Upstream product

• 666750-24-9 (3aS,4S,6aR)-2,2-dimethyltetrahydrothieno[3,4- d][1,3]dioxole-4-carbaldehyde 
• 546-67-8 lead(IV) tetraacetate 
• 96243-58-2 D-gulono-γ-lactone 
• 218906-61-7 methyl 5-thio-β-L-arabinopyranoside 
• 22430-23-5 L-mannono-1,4-lactone 
• 49561-21-9 (3aR,6S,6aR)-6-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one 
• 77-76-9 2,2-dimethoxy-propane 
• 190315-43-6 (2R,3S,4R)-2-(hydroxymethyl)tetrahydrothiophene-3,4-diol 
• 152006-17-2 2,3-O-isopropylidene-L-lyxono-1,4-lactone 
• 1320269-77-9 tert-butyl (((3aS_.4R_.6aR)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxol-4-yl)methoxy)diphenylsilane 
• 1320269-76-8 (3aR,6S,6aR)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one 
• 1006032-29-6 5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-1,4-di-O-methanesulfonyl-L-lyxitol 
• 596103-04-7 (3aS,4R,6aR)-4-((4R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxolane 
• 596103-05-8 (1R)-1-((3aS,4R,6aR)-2,2-dimethyl-tetrahydro-thieno[3,4-d][1,3]dioxol-4-yl)-ethane-1,2-diol 

Downstream Products

• 683275-15-2 benzoic acid (3aS,4R,5R,6aR)-(3aS,4R,5S,6aR)-2,2-dimethyl-5-oxotetrahydro-5λ4-thieno[3,4-d][1,3]dioxol-4-yl methyl ester 
• 596103-09-2 benzoic acid (3aS,4R,6RS,6aR)-6-acetoxy-2,2-dimethyl-tetrahydro-thieno[3,4-d][1,3]dioxol-4-ylmethyl ester 
• 596103-19-4 benzoic acid (3aS,4R,6S,6aR)-6-(2,6-dichloro-purin-9-yl)-2,2-dimethyl-tetrahydro-thieno[3,4-d][1,3]dioxol-4-ylmethyl ester 
• 596103-10-5 benzoic acid (3aS,4R,6R,6aR)-6-(2,6-dichloro-purin-9-yl)-2,2-dimethyl-tetrahydro-thieno[3,4-d][1,3]dioxol-4-ylmethyl ester 
• 666750-35-2 benzoic acid (2R,3S,4R,5R)-5-[2-chloro-6-methylaminopurin-9-yl]-3,4-dihydroxy-tetrahydro-thiophen-2-ylmethyl ester 
• 596103-12-7 benzoic acid (3aS,4R,6R,6aR)-6-(2-chloro-6-methylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-thieno[3,4-d][1,3]dioxol-4-ylmethyl ester 
• 596103-13-8 benzoic acid (3aS,4R,6R,6aR)-6-(6-amino-2-chloro-purin-9-yl)-2,2-dimethyl-tetrahydro-thieno[3,4-d][1,3]dioxol-4-ylmethyl ester 
• 666750-36-3 benzoic acid (2R,3S,4R,5R)-5-[6-amino-2-chloro-purin-9-yl]-3,4-dihydroxytetrahydrothiophen-2-yl methyl ester 
• 596103-01-4 (2S,3S,4R,5R)-5-[2-chloro-6-(3-iodobenzylamino)-purin-9-yl]-3,4-dihydroxy-tetrahydro-thiophene-2-carboxylic acid methylamide 
• 666750-34-1 benzoic acid (2R,3S,4R,5R)-5-[2-chloro-6-(3-iodobenzylamino)purin-9-yl]-3,4-dihydroxy-tetrahydro-thiophen-2-yl methyl ester 
• 596103-11-6 benzoic acid (3aS,4R,6R,6aR)-6-(2-chloro-6-(3-iodo-benzylamino)-purin-9-yl)-2,2-dimethyl-tetrahydro-thieno[3,4-d][1,3]dioxol-4-ylmethyl ester 

Relevant academic research and scientific papers

Synthesis and Properties of 4′-ThioLNA/BNA

To develop a new nucleoside analogue applicable to oligonucleotide therapeutics, we designed a 4′-thio analogue of an LNA/BNA monomer. Synthesis of 4′-hydroxymethyl-4′-thioribonucleoside was achieved by a tandem ring-contraction-aldol reaction of a 5-thio

4-THIORIBOSE NAD ANALOGUES AND METHODS OF SYNTHESIZING AND USING THE SAME

This disclosure provides a method of synthesis of 4'-thioribose NAD+ and analogues thereof, using an efficient chemoenzymatic approach. Also provided are methods of inhibiting the CD38 enzyme and compounds including 4'-thioribose NAD+ and compounds relate

PRMT5 INHIBITORS

The present invention provides a compound of Formula (I) Formula (I) or the pharmaceutically acceptable salts thereof, which are PRMT5 inhibitors.

Biosynthetic Origin of the Atypical Stereochemistry in the Thioheptose Core of Albomycin Nucleoside Antibiotics

Albomycins are peptidyl thionucleoside natural products that display antimicrobial activity against clinically important pathogens. Their structures are characterized by a thioheptose with atypical stereochemistry including a d-xylofuranose ring modified with a d-amino acid moiety. Herein it is demonstrated that AbmH is a pyridoxal 5′-phosphate (PLP)-dependent transaldolase that catalyzes a threo-selective aldol-type reaction to generate the thioheptose core with a d-ribofuranose ring and an l-amino acid moiety. The conversion of l-to d-amino acid configuration is catalyzed by the PLP-dependent epimerase AbmD. The d-ribo to d-xylo conversion of the thiofuranose ring appears according to gene deletion experiments to be mediated by AbmJ, which is annotated as a radical S-adenosyl-l-methionine (SAM) enzyme. These studies establish several key steps in the assembly of the thioheptose core during the biosynthesis of albomycins.

Synthesis of 4′-ethynyl-2′-deoxy-4′-thioribonucleosides and discovery of a highly potent and less toxic NRTI

The synthesis of 4′-ethynyl-2′-deoxy-4′- thioribonucleosides was carried out utilizing an electrophilic glycosidation in which 4-ethynyl-4-thiofuranoid glycal 16 served as a glycosyl donor. Electrophilic glycosidation between 16 and the silylated nucleoba

Synthesis of 4'-thiopurine nucleosides using hypervalent iodine compounds

The reaction of a silylated purine base with thiofuranoid using phenyl iodosyl bis(trifluoroacetate) gave 4'-thio purine nucleosides.

Structure-activity relationships of 2-chloro-N6-substituted- 4′-thioadenosine-5′-uronamides as highly potent and selective agonists at the human A3 adenosine receptor

We have established structure-activity relationships of novel 4′-thionucleoside analogues as the A3 adenosine receptor (AR) agonists. Binding affinity, selectivity toward other AR subtypes, and efficacy in inhibition of adenylate cyclase were studied. Fro

A practical synthesis of 4′-thioribonucleosides

A practical synthesis of 4′-thioribonucleosides starting from inexpensive l-arabinose is described. 1,4-Anhydro-2,3-O-isopropylidene-4- thioribitol, which was prepared by using a novel reductive ring-contraction reaction, was converted to the 5-O-silylated sulfoxides. The Pummerer-type thioglycosylation of the sulfoxides gave the 4′-thioribonucleosides stereoselectively.

Purine nucleosides

Disclosed are purine nucleoside compounds that are selective to A3 adenosine receptors and are useful for the treatment of cancer and inflammatory diseases. The compounds are shown by the following general formula (I), including isomers thereof: wherein X is sulfur or oxygen; R1 is hydrogen, alkyl, benzyl, halobenzyl, or phenylalkyl; R2 is hydrogen, halogen, alkoxy, alkenyl, alkynyl, alkylthio, or thio; R3 and R3′ are hydrogen, hydroxyalkyl, alkoxycarbonyl, or alkylaminocabonyl, whereas R3 and R3′ do not have identical substituents simultaneously; and R4 is hydrogen or alkyl. Also disclosed are a pharmaceutical composition comprising a compound of formula (I), an isomer, or its pharmacologically acceptable salt as an active ingredient and a method for preventing or treating various diseases, state, or condition, including asthma, inflammation, cerebral ischemia, heart diseases, and cancer.

N6-substituted D-4′-thioadenosine-5′-methyluronamides: Potent and selective agonists at the human A3 adenosine receptor

4′-Thio analogues 3-5 of Cl-IB-MECA (2) (Ki = 1.0 ± 0.2 nM at the human A3 adenosine receptor) were synthesized from D-gulono-γ-lactone via 4-thioribosyl acetate 14 as the key intermediate. All synthesized 4′-thionucleosides exhibite