M5890
Methyl 1,2,3,4-tetra-O-acetyl-β-D-glucuronate
≥98% (GC)
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About This Item
Empirical Formula (Hill Notation):
C15H20O11
CAS Number:
Molecular Weight:
376.31
NACRES:
NA.25
PubChem Substance ID:
UNSPSC Code:
12352201
EC Number:
230-880-3
MDL number:
form
powder
InChI key
DPOQCELSZBSZGX-UHFFFAOYSA-N
InChI
1S/C15H20O11/c1-6(16)22-10-11(23-7(2)17)13(24-8(3)18)15(25-9(4)19)26-12(10)14(20)21-5/h10-13,15H,1-5H3
SMILES string
COC(=O)C1OC(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O
biological source
synthetic (organic)
assay
≥98% (GC)
optical activity
[α]20/D 8.1 to 9.5 °, c = 1% (w/v) in chloroform
technique(s)
gas chromatography (GC): suitable
storage temp.
2-8°C
Application
Methyl 1,2,3,4-tetra-O-acetyl-β-D-glucuronate has been used in a study to assess design and synthesis of a water-soluble glucuronide derivatives of camptothecin for cancer prodrug monotherapy and antibody-directed enzyme prodrug therapy. It has also been used in a study to investigate the synthesis and role of glycosylthio heterocycles in carbohydrate chemistry.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Regulatory Information
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Synthesis and role of glycosylthio heterocycles in carbohydrate chemistry
Ashry, E., et al.
Tetrahedron, 62, 2943-2998 (2006)
Y L Leu et al.
Journal of medicinal chemistry, 42(18), 3623-3628 (1999-09-10)
Glucuronide prodrugs of 9-aminocamptothecin were synthesized. Prodrug 4, in which 9-aminocamptothecin was connected to glucuronic acid by an aromatic spacer via a carbamate linkage, was stable in both aqueous solution and human plasma. Prodrug 4 and its potassium salt 12
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