14152-97-7

Basic information

• Product Name: 2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSYL ISOTHIOCYANATE
• Synonyms: 2,3,4,6-TETRA-O-ACETYL-B-D-*GLUCOPYRANOS YL ISOTHIOC;2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSYL ISOTHIOCYANATE [FOR HPLC LABELING];2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSYL ISOTHIOCYNATE;2,3,4,6-TETRA-O-ACETYL-SS-D-GLUCOPYRANOSYL ISOTHIOCYANATE;GITC [2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSYL ISOTHIOCYANATE];1-Isothiocyanato-1-deoxy-β-D-glucopyranose 2,3,4,6-tetraacetate;Tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate;2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate ,98%
• CAS NO: 14152-97-7
• Molecular Formula: C₁₅H₁₉NO₉S
• Molecular Weight: 389.38
• Product Categories: pharmacetical;Amino Group Labeling Reagents for HPLC;Analytical Chemistry;Biochemistry;e.e. Determination (HPLC Labeling Reagents);Enantiomer Excess & Absolute Configuration Determination;Glucose;Glycosides;HPLC Labeling Reagents;O-Substituted Sugars;Sugars;UV Detection (HPLC Labeling Reagents);Carbohydrates
• Mol File: 14152-97-7.mol
• Article Data: 36

Chemical Properties

• Melting Point: 114-116 °C(lit.)
• Boiling Point: 469.7 °C at 760 mmHg
• Flash Point: 237.8 °C
• Appearance: /
• Density: 1.4 g/cm³
• Vapor Pressure: 5.4E-09mmHg at 25°C
• Refractive Index: 1.556
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Sparingly), Methanol (Slightly)
• BRN: 56699
• CAS DataBase Reference: 2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSYL ISOTHIOCYANATE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSYL ISOTHIOCYANATE(14152-97-7)
• EPA Substance Registry System: 2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSYL ISOTHIOCYANATE(14152-97-7)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-42
• Safety Statements: 22-26-36-45
• RIDADR: 2810
• WGK Germany: 3
• F: 3-8-21
• Hazardous Substances Data: 14152-97-7(Hazardous Substances Data)

Usage

Description

2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate is a chiral derivatization reagent that is primarily utilized for the resolution of enantiomeric amino acid derivatives. It is a white to off-white powder in its chemical form, known for its specific interactions with amino acids.

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 
• 4000-25-3 tetra-O-acetyl-N-[3-(2-chloro-ethyl)-thiazolidin-2-ylidene]-β-D-glucopyranosylamine 
• 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 

Relevant articles and documents

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

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.

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.