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M5890

Sigma-Aldrich

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:
7355-18-2
Molecular Weight:
376.31
EC Number:
230-880-3
MDL number:
MFCD00069834
UNSPSC Code:
12352201
PubChem Substance ID:
24897053
NACRES:
NA.25
Pricing and availability is not currently available.

biological source

synthetic (organic)

Assay

≥98% (GC)

form

powder

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

SMILES string

COC(=O)C1OC(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O

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

InChI key

DPOQCELSZBSZGX-UHFFFAOYSA-N

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. [1] It has also been used in a study to investigate the synthesis and role of glycosylthio heterocycles in carbohydrate chemistry. [2]

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BGBB4658V
BGBB4658
075K37943V
075K37943
075K37942

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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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