14152-97-7

Usage

Uses

Used in Pharmaceutical Industry:
2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate is used as a chiral reagent for the resolution of amino acid derivatives. This application is significant in the pharmaceutical industry as it aids in the separation and identification of enantiomers, which are crucial for the development of effective drugs with minimal side effects.
Used in Analytical Chemistry:
In the field of analytical chemistry, 2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate serves as a valuable chiral derivatization reagent. It is employed to enhance the detection and analysis of enantiomeric amino acids, contributing to the advancement of research in stereochemistry and the development of novel chiral compounds.
Used in Research and Development:
2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate is also used in research and development for the synthesis of various chiral compounds and the study of their properties. Its ability to react with enantiomeric amino acids makes it a valuable tool in the exploration of new drug candidates and the understanding of chiral interactions at the molecular level.

InChI:InChI=1/C15H19NO9S/c1-7(17)21-5-11-12(22-8(2)18)13(23-9(3)19)14(24-10(4)20)15(25-11)16-6-26/h11-15H,5H2,1-4H3

Upstream product

• 333-20-0 potassium thioacyanate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 592-87-0 lead(II) thiocyanate 
• 2290-65-5 trimethylsilyl isothiocyanate 
• 604-69-3 β-D-glucose pentaacetate 
• 463-71-8 thiophosgene 
• 525589-11-1 2-methyl-4,5-dihydro-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyrano)[2,1-d]-2-oxazoline 
• 1147550-11-5 ammonium thiocyanate 
• 6919-96-6 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 41355-50-4 2,3,4,6-tetra-O-acetyl-D-glucosyl-1-amine 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 3068-32-4 1-bromo-2,3,4,6-tetra-O-acetyl-D-galactopyranose 
• 83-87-4 penta-O-acetyl-α-D-galactopyranose 
• 572-09-8 acetobromogalactose 

Downstream Products

• 76822-35-0 N-β-D-glucopyranosylthiourea 
• 50802-49-8 β-D-glucopyranosyl isothiocyanate 
• 121388-83-8 1-(4'-Phenylthiazol-2'-yl)-2-tetra-O-acetyl-β-D-glucopyranosyl thiocarbamide 
• 121388-69-0 Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-{3-[4-(4-chloro-phenyl)-thiazol-2-yl]-thioureido}-tetrahydro-pyran-3-yl ester 
• 79857-61-7 C₃₁H₅₃N₃O₁₀S 
• 81812-49-9 C₂₂H₂₇N₃O₉S 
• 77489-38-4 2,3,4,6-tetra-O-acetyl-1-N--β-D-glucopyranosylamine 
• 108275-73-6 N-(p-bromophenacyl)-N'-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiourea 
• 105014-62-8 N-(p-methylphenyl)-N'-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiourea 
• 121388-67-8 1-tetra-O-acetyl-β-D-glucopyranosyl-3-p-chlorophenylthiourea 
• 69435-06-9 C₂₂H₂₇N₃O₁₀S 
• 121388-68-9 Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[3-(4-nitro-phenyl)-thioureido]-tetrahydro-pyran-3-yl ester 
• 108967-47-1 N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-N'-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)thiourea 
• 109062-65-9 N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-N'-(2,3,4,6-tetra-O-benzoyl-α-D-galactopyranosyl)thiourea 

Relevant academic research and scientific papers

Synthesis and Antimicrobial Activities of 1,2,4-Thiadiazolidin-3-thione Hydrochlorides

Synthesis of N-glucosyl/lactosyl/maltosyl-1,2,4-thiadizolidin-3-thione hydrochlorides by the reaction of N-phenyl-S-chloroisothiocarbamoyl chloride and N-glucosyl/lactosyl/maltosyl thiocarbamides is reported. The simple isolation method with good yields under mild condition is applicable for the present protocol. All the newly synthesized thiadiazolidin-3-thiones exhibit moderate to good antimicrobial activities against a variety of pathogen

Thiourea-containing arsenic sugar with anti-tumor activity and preparation method and application thereof

The invention relates to the field of arsenic sugar, and in particular relates to thiourea-containing arsenic sugar with anti-tumor activity and a preparation method and application thereof. The thiourea-containing arsenic sugar is composed of two compounds: 1-(N-(4'-(1'', 3'', 2''-dithiaarsenic pentane-2-yl) phenyl)-thiourea)-2, 3, 4, 6-O-acetyl-beta-D-glucose and 1-(N-(4'-(1'', 3 '', 2''-dithiaarsenic hexane-2-yl) phenyl)-thiourea)-2, 3, 4, 6-O-acetyl-beta-D-glucose. The thiourea-containing arsenic sugar provided by the invention has the advantages of simple reaction operation and high yield. The thiourea-containing arsenic sugar with a specific three-dimensional configuration can be obtained, and the thiourea-containing arsenic sugar has good anti-tumor activity.

Synthesis and schematic mechanism of 3-phenylamino-4-phenyl-5-tetra-O-acetyl-β-D-glucopyranosylimino-1,2,4-dithiazolidines and Its De-acetylated Nucleoside

A systematic synthesis of 3-phenylimino-4-phenyl-5-tetra-O-acetyl-β-D-glucopyranosylimino-1,2,4-dithiazolidine (acetylated glucopyranosylimino nucleoside) from glucose as starting material. The steps included acetylating glucose to glucose penta-acetate (II). Step 2 involves the bromination of glucose penta-acetate (II) to 2,3,4,6 tetra-O-acetyl-α-D-glucopyranosyl bromide (III). In step 3 compound (III) reacted with lead thiocyanate to give 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate (IV). In the step 4 N-phenyl-3-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate (V) was prepared. In the last step on refluxing compound (V) with N-phenyl S-chloro isothiocarbamoyl chloride to yield acetylated glucopyranosyl nucleoside. Furthermore de-acetylating of acetylated glucopyranosyl nucleoside was carried out to obtain 3-phenylimino-4-phenyl-5-β-D-gluopyranosyl imino 1,2,4-dithiazolidine (de-acetylated glucopyranosylimino nucleoside). The synthesized acetylated glucopyranosylimino nucleoside and deacetylated glucopyranosylimono nucleoside were structurally confirmed by elemental analysis, ultraviolet spectral analysis, infrared spectroscopy, nuclear magnetic resonance spectroscopy and mass spectroscopy.

Matrix metalloproteinase-12 inhibitors: synthesis, structure-activity relationships and intestinal absorption of novel sugar-based biphenylsulfonamide carboxylates

MMP-12 is a validated target in pulmonary and cardiovascular diseases. The principal obstacles to clinical development of MMP-12 inhibitors are an inadequate selectivity for the target enzyme and a poor water solubility, with consequent poor oral bioavailability. We recently reported a new class of sugar-based arylsulfonamide carboxylates with a nanomolar activity for MMP-12, a good selectivity and an improved water solubility. In this study, we designed and synthesized new derivatives to characterize the structure-activity relationship (SAR) within this class of glycoconjugate inhibitors. All the new derivatives were tested on human recombinant MMP-12 and MMP-9 in order to evaluate their affinity and the selectivity for the target enzyme. Among them, the four most promising compounds were selected to assess their intestinal permeability using an ex vivo everted gut sac model. Given the high polarity and structural similarity to glucose, compound 3 was demonstrated to cross the intestinal membrane by using the facilitative GLUT2 transport.

Synthesis and biological activity of novel N-glucosides containing substituted piperazine moiety

A series of novel acetylated piperazine-containing N-glucosides and bis(N-glucoside) 8a-i were synthesized by the nucleophilic addition of acetylated glucopyranosyl isothiocyanate with various substituted piperazines in THF with high yields. Their novel deacetylated products 9a-i were also synthesized after Me-ONa/MeOH treatment. The preliminary bioassays for 18 novel title compounds showed that several compounds have significant fungicidal activity against Fusarium omysporum, Cercospora arachidicola and Phytophthora capsici at 50 μg/mL.

Synthesis and evaluation of in?vivo antioxidant, in?vitro antibacterial, MRSA and antifungal activity of novel substituted isatin N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiosemicarbazones

Some new isatin N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiosemicarbazones 4a-t with different substituents at 1-, 5- and 7-positions of isatin ring have been synthesized by reaction of N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiosemicarbazide 2 with corresponding isatins 3a-t. Compounds 4a-t were evaluated in?vivo for antioxidant activity and in?vitro for anti-microorganism activities. The MIC values were found for Gram positive bacteria (MIC?=?1.56–6.25?μM), for Gram negative bacteria (MIC?=?12.5?μM), and for fungi Aspergillus niger (MIC?=?3.12–12.5?μM), Fusarium oxysporum (MIC?=?6.25–12.5?μM) and Saccharomyces cerevisiae (MIC?=?6.25–12.5?μM). Regarding the antioxidant activity, the SOD, GHS-Px and catalase activities of 4c-i and 4m-r were MIC?=?10.57–10.85, 0.27–0.93 and 345.45–399.75 unit/mg protein, respectively. Compounds 4e-h had MIC values of 0.78, 1.56, and 3.12?μM for three clinical MRSA isolates. Compound 4e showed the selective cytotoxic effects against some cancer (LU-1, HepG2, MCF7, P338, SW480, KB) cell lines and normal fibroblast cell line NIH/3T3.

Synthesis of some new carbohydrate-containing thiouriedonaphtho-quinones

Abstract New alkyl, aryl, and glycosylthiouriedo derivatives of 2,3-diamino-1,4-naphthoquinone were synthesized via the reaction of isothiocyanates with 2,3-diamino-1,4-naphthoquinone. The new compounds were fully characterized through their physicochemical properties.

Synthesis and Characterization of N -glucosylated 1,3,4-Thiadiazolidines

A method is presented for the synthesis of 2-tetra-O-acetyl-β-d-glucopyranbreak; osylimino-5-(aryl)imino-1,3,4-thiadiazolidines by the interaction of substituted aryl thiosemicarbazide with peracetylated glucosyl isocyanodichloride to afford N-glucosylate

Thiourea linked peracetylated glucopyranosyl-anthraquinone conjugate as reversible ON-OFF receptor for fluoride in acetonitrile

A new thiourea linked peracetylated glucopyranosyl-anthraquinone conjugate (L) has been synthesized and characterized. The binding properties of L have been studied with nineteen different anions. The L exhibited selective chromogenic as well as fluorescent chemosensor property toward F- by a ～13-fold increase in the emission intensity upon binding with F -. The minimal detection limit for F- is 185 ± 5 ppb in acetonitrile. Interaction of F- led to a bathochromic shift of 80 nm in the absorption band. An INHIBIT logic gate has been proposed using the output obtained from the fluorescence studies. The structure of the species formed upon the interaction of F- with L has been established by DFT computations.

Design and synthesis of thiourea compounds that inhibit transmembrane anchored carbonic anhydrases

A library of 32 novel glycoconjugate thiourea-bridged benzene sulfonamides have been synthesized from the reaction of glycosyl isothiocyanates with a panel of simple benzene sulfonamides comprising either a free amine or hydrazide. All compounds were inve