16667-96-2

Usage

Uses

Used in Organic Synthesis:
1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose S-Methyl Dithiocarbonate is used as a synthetic intermediate for the preparation of various organic compounds. Its unique structure allows for selective reactions and modifications, making it a valuable building block in the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose S-Methyl Dithiocarbonate is used as a key intermediate in the synthesis of bioactive compounds, such as antibiotics, antiviral agents, and other therapeutic agents. Its ability to form stable derivatives and participate in various chemical reactions makes it a versatile component in drug development.
Used in Chemical Research:
1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose S-Methyl Dithiocarbonate is also used in chemical research for studying the properties and reactivity of complex organic molecules. Its unique structure provides insights into the behavior of similar compounds and contributes to the advancement of organic chemistry.
Used in Material Science:
In material science, 1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose S-Methyl Dithiocarbonate can be used as a component in the development of new materials with specific properties, such as polymers, coatings, and adhesives. Its ability to form stable derivatives and participate in various chemical reactions makes it a promising candidate for material innovation.

InChI:InChI=1/C14H22O6S2/c1-13(2)15-6-7(18-13)8-9(17-12(21)22-5)10-11(16-8)20-14(3,4)19-10/h7-11H,6H2,1-5H3

Upstream product

• 64656-76-4 Natrium-Verbindung der O¹,O²;O⁵,O⁶-Diisopropyliden-α-D-glucofuranose 
• 75-15-0 carbon disulfide 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 74-88-4 methyl iodide 
• 2280-44-6 D-Glucose 
• 288-32-4 1H-imidazole 
• 74-83-9 methyl bromide 
• 350255-13-9 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 

Downstream Products

• 17668-62-1 1,2:5,6-Di-O-isopropyliden-3-S-(methylthio)-carbonyl-3-thio-α-D-glucofuranose 
• 67-47-0 5-hydroxymethyl-2-furfuraldehyde 
• 1255906-08-1 C₁₅H₁₉NO₃ 
• 1365659-13-7 (3R,5S)-5-[((phenylmethyl(benzyloxycarbonyl)amino)methyl)-2-(R/S)-methoxy-tetrahydrofuran-3-yl]methanesulfonate 
• 1365659-10-4 N-benzyl-((3aR,5S,6aR)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanamine 
• 1365659-11-5 benzyl benzyl((3aR,5S,6aR)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)carbamate 
• 1365659-12-6 benzyl benzyl(((3R)-hydroxy-2(R/S)-methoxy-(5S)-tetrahydrofuran2-yl)methyl)carbamate 
• 4005-46-3 3-deoxy-1,2-O-isopropylidene-D-glucose 
• 2774-29-0 (3aR,5R,6aR)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole 
• 88326-26-5 3-[(3aR,5R,6S,6aR)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-propionitrile 
• 765300-56-9 (3R,5S)-3-(benzyloxy)-5-vinyltetrahydrofuran-2-ol 
• 23655-60-9 (2S,3R,5S)-5-((S)-1,2-diacetoxyethyl)tetrahydrofuran-2,3-diyl diacetate 
• 7284-15-3 2-deoxy-D-ribonic acid 
• 17510-99-5 4,5,6-trihydroxy-2-oxohexanoic acid 

Relevant academic research and scientific papers

3-O-Acyl triggered tandem Lewis acid catalyzed intramolecular cyclization of diacetone glucose derivatives to 5-O-acyl-3,6-anhydro-d-glucose

BF3 mediated one-pot conversion of 3-O-acyl-d-glucose-1,2:5,6- diacetonide derivatives to 5-O-acyl-3,6-anhydro-d-glucose is described through a tandem selective intramolecular cyclization sequence.

TLR7 AGONISTS

The present invention relates to TLR7 agonists according to Formula I and their use in the treatment of diseases such as cancer and infectious disease.

A new scalable synthesis of entecavir

A new synthesis of entecavir from D-glucose in an average total yield of 3.5% was achieved via an intramolecular nitrile oxide cycloaddition (INOC) reaction and a Peterson olefination as key-steps. The present process was designed for industrial application, using widely available raw materials, simple and cheap reagents and avoiding low reaction temperatures, which are very common in the synthetic approaches towards similarly complex structures.

THE TOTAL SYNTHESIS OF GLUCOSEPANE AND COMPOUNDS OBTAINED THEREFROM

Glucosepane is a structurally complex protein post-translational modification (PTM) believed to exist in all living organisms. Research in humans suggests that glucosepane plays a critical role in the pathophysiology of both diabetes and human aging; yet

NOVEL 3-SUBSTITUTED 5-AMINO-6H-THIAZOLO[4,5-D]PYRIMIDINE-2,7-DIONE COMPOUNDS FOR THE TREATMENT AND PROPHYLAXIS OF VIRUS INFECTION

The present invention relates to compounds of formula (I), wherein R1, R2 and R3 are as described herein, and their prodrugs or pharmaceutically acceptable salt, enantiomer or diastereomer thereof, and compositions including the compounds and methods of using the compounds.

Synthesis of modified Trichinella spiralis disaccharide epitopes and a comparison of their recognition by chemical mapping and saturation transfer difference NMR

A rat monoclonal antibody 9D4 raised against the cell surface N-glycan of the parasite Trichinella spirallis protects rats against further infection. The terminal disaccharide β-d-Tyvp(1→3)β-d-GalNAcp (2) represents the immunodominant portion of the antig

Reactivity of thermally treated α-dicarbonyl compounds

The degradation reaction of thermally treated 3-deoxy-d-erythro-hexos-2- ulose and methylglyoxal, both key intermediates in Maillard chemistry, was investigated. Different analytical strategies were accomplished to cover the broad range of formed products and their different chemical behavior. These involved HPLC-DAD and accordingly LC/MS analysis of the quinoxaline derivates, GC/MS analysis of the acetylated quinoxalines, and GC-FID analysis of the decyl ester of acetic acid. As a main degradation product of 3-deoxy-d-erythro-hexos- 2-ulose, 5-(hydroxymethyl)furfural could be identified. At alkaline pH values, 3-deoxy-d-erythro-hexos-2-ulose generated various acids but no colored products. In contrast, thermal treatment of methylglyoxal yielded high molecular weight, brownish products. A dimer of methylglyoxal, first precursor for aldol-based polymerization of methylglyoxal, could be clearly identified by GC/MS.

Asymmetric three-component domino reaction: An original access to chiral nonracemic 1,3-thiazin-2-ones

A new asymmetric three-component domino process, based on a diastereoselective hetero-Diels-Alder reaction, involving an aldehyde, an alkene, and a chiral thiocarbamate was developed. The chiral auxiliary is directly removed during this process, leading to enantioenriched 2H-1,3-thiazin-2-ones with up to 96% ee.

Synthesis of (2S,4S)-4-hydroxyproline from D-glucose

Diacetone-D-glucose 1 gives 3-O-methylxanthate 2 on reaction with NaH=Me I. Reductive deoxygenation of compound 2 by Bu3SnH gives the corresponding 3-deoxy glucose derivative 3 and on acid-catalyzed regioselective deprotection of C-5,6-acetonide gives the diol 4. The diol on oxidative cleavage with NaIO4 gives the aldehyde 5, which on further condensation with benzylamine followed by reduction with NaBH4 gives the amine 7. Z-Protection of the amine followed by methanolysis gives methyl furanoside 9. Reaction of 9 with methanesulfonyl chloride=Et3N gives the corresponding C-3-O-mesylate derivative 10. Catalytic hydrogenation of compound 10 (Pd=C=H2=MeOH 3 kg) gives bicyclic oxaazo compound 11, due to deprotection of the N-benzyl- and Z-protecting groups and intramolecular nucleophilic displacement of the C-2-O-mesylate by the C-5 amine in a one-pot reaction. Z-Protection of the amine 11 followed by acid-catalyzed hydrolysis gives acetal 13. Reduction of acetal by use of NaBH4 gives Z-prolinol 14. Selective oxidation of diol 14 by (2,2,6,6-tetramethylpiperidin-1-yl)-oxyl (TEMPO)=[(bis)(acetoxy)iodo]-benzene (BAIB) and NaClO2=NaH 2PO4, followed by Z-deprotection, gives the title compound I in 3.5% overall yield from D-glucose. Copyright Taylor & Francis Group, LLC.

Synthesis of locked pyranosyl nucleic acid (LpNA)

A new locked pyranosyl nucleoside was synthesized by phenylsulfinyl- assisted chemistry. The novel building block was inserted into oligonucleotides and provides new insight on conformational restricted pyranosyl nucleosides on duplex formation