1-Azido-1-deoxy-β-D-glucopyranoside tetraacetate - CAS 13992-25-1
Catalog: |
BB009006 |
Product Name: |
1-Azido-1-deoxy-β-D-glucopyranoside tetraacetate |
CAS: |
13992-25-1 |
Synonyms: |
2,3,4,6-Tetra-O-acetyl-1-deoxy-β-D-glucopyranosyl azide; β-D-Glucopyranosyl Azide 2,3,4,6-Tetraacetate; 1-β-Azido-2,3,4,6-tetraacetyl-D-glucopyranose; 2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl azide; NSC 272456; 1-Azido-1-deoxy-beta-D-glucopyranose tetraacetate; (2R,3R,4S,5R,6R)-2-(Acetoxymethyl)-6-azidotetrahydro-2H-pyran-3,4,5-triyl triacetate |
IUPAC Name: | [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-azidooxan-2-yl]methyl acetate |
Description: | 1-Azido-1-deoxy-β-D-glucopyranoside tetraacetate (CAS# 13992-25-1) is an intermediate used for the synthesis of Protein Tyrosine Phosphatase 1B inhibito1. It is used for the preparation of variously coupled conjugates of D-glucose via click chemistry for inhibition of glycogen phosphorylase. |
Molecular Weight: | 373.32 |
Molecular Formula: | C14H19N3O9 |
Canonical SMILES: | CC(=O)OCC1C(C(C(C(O1)N=[N+]=[N-])OC(=O)C)OC(=O)C)OC(=O)C |
InChI: | InChI=1S/C14H19N3O9/c1-6(18)22-5-10-11(23-7(2)19)12(24-8(3)20)13(25-9(4)21)14(26-10)16-17-15/h10-14H,5H2,1-4H3/t10-,11-,12+,13-,14-/m1/s1 |
InChI Key: | NHNYHKRWHCWHAJ-RKQHYHRCSA-N |
Melting Point: | 127-131°C |
Purity: | ≥95% |
Appearance: | White to Off-white Crystalline Powder |
Storage: | Store at 2-8°C |
MDL: | MFCD00181721 |
LogP: | -0.16744 |
Publication Number | Title | Priority Date |
RU-2691754-C1 | DERIVATIVE OF ZINC METAL COMPLEX CHLORINE-e6 AND USE THEREOF | 20181115 |
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JP-2019527040-A | Metabolic labeling and molecular enhancement of biomaterials using bioorthogonal reactions | 20160615 |
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PMID | Publication Date | Title | Journal |
19345445 | 20090901 | Synthesis and cytotoxic profile of glycosyl-triazole linked to 1,2,4-oxadiazole moiety at C-5 through a straight-chain carbon and oxygen atoms | European journal of medicinal chemistry |
16678807 | 20060703 | N-glycoside neoglycotrimers from 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl azide | Carbohydrate research |
16564511 | 20060612 | Synthesis of N-(beta-D-glucopyranosyl) monoamides of dicarboxylic acids as potential inhibitors of glycogen phosphorylase | Carbohydrate research |
Complexity: | 617 |
Compound Is Canonicalized: | Yes |
Covalently-Bonded Unit Count: | 1 |
Defined Atom Stereocenter Count: | 5 |
Defined Bond Stereocenter Count: | 0 |
Exact Mass: | 373.11212919 |
Formal Charge: | 0 |
Heavy Atom Count: | 26 |
Hydrogen Bond Acceptor Count: | 11 |
Hydrogen Bond Donor Count: | 0 |
Isotope Atom Count: | 0 |
Monoisotopic Mass: | 373.11212919 |
Rotatable Bond Count: | 10 |
Topological Polar Surface Area: | 129 |
Undefined Atom Stereocenter Count: | 0 |
Undefined Bond Stereocenter Count: | 1 |
XLogP3: | 0.7 |
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