2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate（GITC） - ≥98% , CAS No.14152-97-7

CAS: 14152-97-7 Cat. No.: T115333 Molecular Weight: 389.38 Beilstein Registry Number: 56699 EC Number: 625-090-4 PubChem CID: 99462

GRADE & PURITY ≥98%

Synonyms

(2R,3R,4S,5R,6R)-2-(Acetoxymethyl)-6-isothiocyanatotetrahydro-2H-pyran-3,4,5-triyltriacetate | GITC | 2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl isothiocyanate, for chiral derivatization, >=98.0% (HPLC) | 2,3,4,6-Tetra-O-acetylglucopyranosylisothiocyana

Storage

Store at 2-8°C,Argon charged

Shipped In

Wet ice

Overview

Chiral reagent for resolution of amino acid derivatives.

Specifications

Synonyms

(2R, 3R, 4S, 5R, 6R)-2-(Acetoxymethyl)-6-isothiocyanatotetrahydro-2H-pyran-3, 4, 5-triyltriacetate | GITC | 2, 3, 4, 6-Tetra-O-acetyl-beta-D-glucopyranosyl isothiocyanate, for chiral derivatization, >=98.0% (HPLC) | 2, 3, 4, 6-Tetra-O-acetylglucopyranosylisothiocyana

Specifications & Purity

≥98%

Storage

Store at 2-8°C, Argon charged

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 504756438
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504756438
• Canonical Smiles: CC(=O)OCC1C(C(C(C(O1)N=C=S)OC(=O)C)OC(=O)C)OC(=O)C
• IUPAC Name: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-isothiocyanatooxan-2-yl]methyl acetate
• InChIKey: WOWNQYXIQWQJRJ-UXXRCYHCSA-N
• INCHI: 1S/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/t11-,12-,13+,14-,15-/m1/s1
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)N=C=S)OC(=O)C)OC(=O)C)OC(=O)C
• WGK Germany: 3
• PubChem CID: 99462
• Molecular Weight: 389.38
• Beilstein: 56699
• Reaxy-Rn: 56699

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Tetracarboxylic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Tetracarboxylic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Tetracarboxylic acids and derivatives
• Alternative Parents: Glycosylamines Oxanes Monosaccharides Isothiocyanates Carboxylic acid esters Propargyl-type 1,3-dipolar organic compounds Oxacyclic compounds Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: Tetracarboxylic acid or derivatives - Glycosyl compound - N-glycosyl compound - Monosaccharide - Oxane - Carboxylic acid ester - Isothiocyanate - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Organoheterocyclic compound - Oxacycle - Hydrocarbon derivative - Organic oxide - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Organopnictogen compound - Carbonyl group - Organic oxygen compound - Organic nitrogen compound - Aliphatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: Soluble in dichloromethane
• Sensitivity: Moisture sensitive，light sensitive
• Boil Point(°C): 116°C
• Melt Point(°C): 114-116°C
• Molecular Weight: 389.400 g/mol
• XLogP3: 1.200
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 10
• Exact Mass: 389.078 Da
• Monoisotopic Mass: 389.078 Da
• Topological Polar Surface Area: 159.000 Ų
• Heavy Atom Count: 26
• Formal Charge: 0
• Complexity: 616.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 5
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Xiaoxiang Hu, Yajun Bai, Tai-Ping Fan, Xiaohui Zheng, Yujie Cai.  (2020)  A novel type alanine dehydrogenase from Helicobacter aurati: Molecular characterization and application.  INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,      [PMID:32534087] [10.1016/j.ijbiomac.2020.06.067]

2. Zhang Zhi-Jun, Cai Rui-Feng, Xu Jian-He.  (2018)  Characterization of a new nitrilase from Hoeflea phototrophica DFL-43 for a two-step one-pot synthesis of (S)-β-amino acids.  APPLIED MICROBIOLOGY AND BIOTECHNOLOGY,  102  (14): (6047-6056).  [PMID:29744634] [10.1007/s00253-018-9057-7]

3. Wenkai Hui, Lili Sun, Hui Zhang, Liang Zou, Qiaogen Zou, Pingkai Ouyang.  (2016)  Quantitative analysis of ripasudil hydrochloride hydrate and its impurities by reversed-phase high-performance liquid chromatography after precolumn derivatization: Identification of four impurities.  JOURNAL OF SEPARATION SCIENCE,  39  (17): (3302-3310).  [PMID:27390135] [10.1002/jssc.201600278]