1,2,3,4-Tetra-o-acetyl-ß-D-glucopyranuronate

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Names

[ Name ]:
1,2,3,4-Tetra-o-acetyl-ß-D-glucopyranuronate

[Synonym ]:
T6OTJ BVO1 COV1 DOV1 EOV1 FOV1 &&β-D-Gluco Form
1,2,3,4-Tetra-o-acetyl-ß-D-glucopyranuronate
Methyl 3,4,5,6-tetra(acetyloxy)tetrahydro-2H-pyran-2-carboxylate
Methyl 1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronate
Methyl O-tetraacetyl-β-D-glucopyranuronate
Methyl 1,2,3,4-Tetra-O-acetyl-β-D-glucuronate
EINECS 230-880-3
β-D-Glucopyranuronic acid, methyl ester, 1,2,3,4-tetraacetate
β-D-Glucopyranuronic acid, methyl ester, tetraacetate
MFCD00069834

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
412.3±45.0 °C at 760 mmHg

[ Melting Point ]:
179 °C

[ Molecular Formula ]:
C₁₅H₂₀O₁₁

[ Molecular Weight ]:
376.31

[ Flash Point ]:
178.4±28.8 °C

[ Exact Mass ]:
376.100555

[ PSA ]:
140.73000

[ LogP ]:
1.88

[ Vapour Pressure ]:
0.0±1.0 mmHg at 25°C

[ Index of Refraction ]:
1.482

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

Methanol
(1S,2R,3R,5S)-2,3,6-trihydroxy-4,8-dioxabicyclo[3.3.0]octan-7-one
Ethanoic anhydride
Sodium Methylate
D-glucuronic acid methyl ester
Acetyl chloride
.beta.-D-Glucopyranuronic acid, 5-C-bromo-, methyl ester, tetraacetate
acetic acid
Methyl acetobromo-α-D-glucuronate

DownStream

Methyl Tri-O-acetyl-1-naphthol Glucuronate
Estrone 3-glucuronide
Methyl acetobromo-α-D-glucuronate
METHYL 2,3,4-TRI-O-ACETYL-BETA-D-GLUCOPYRANURONOSYL AZIDE
17β-Estradiol 3-β-D-Glucuronide
phenyl-beta-d-glucuronide
3,4,6-TRI-O-ACETYL-ALPHA-D-GLUCOPYRANOSE 1,2-(METHYL ORTHOACETATE)
2-Nitrophenyl 2,3,4-Tri-O-acetyl-β-D-glucuronide, Methyl Ester
3-methylthiazolo[3,2-a]benzimidazole-2-carboxylic acid ethyl ester
b-D-Glucopyranuronic acid,1-deoxy-1-(3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl)-,methyl ester, 2,3,4-triacetate

Articles

Design and synthesis of water-soluble glucuronide derivatives of camptothecin for cancer prodrug monotherapy and antibody-directed enzyme prodrug therapy (ADEPT).

J. Med. Chem. 42 , 3623-8, (1999)

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...

Synthesis and role of glycosylthio heterocycles in carbohydrate chemistry Ashry, E., et al.

Tetrahedron 62 , 2943-98, (2006)

1,2,3,4-TETRA-O-ACETYL-D-XYLOPYRANOSE
1,2,3,4-TETRA-O-ACETYL-D-GLUCOPYRANURONIC ACID METHYL ESTER
1,2,3,4-Tetra-O-acetyl-D-xylopyranose
1,2,3,4-Tetra-O-acetyl-D-lyxopyranose
.beta.-D-Glucopyranuronic acid, ethyl ester, tetraacetate
.beta.-D-Glucopyranuronic acid, 5-C-bromo-, methyl ester, tetraacetate
N-[(3,4-dimethylphenyl)methyl]oxan-4-amine
N-(2,6-dimethylphenyl)-2-(7-methyl-3-(4-methylpiperidine-1-carbonyl)-4-oxo-1,8-naphthyridin-1(4H)-yl)acetamide
N-(3,5-dimethylphenyl)-2-(7-methyl-3-(4-methylpiperidine-1-carbonyl)-4-oxo-1,8-naphthyridin-1(4H)-yl)acetamide
N-(2,5-dimethylphenyl)-2-(7-methyl-3-(4-methylpiperidine-1-carbonyl)-4-oxo-1,8-naphthyridin-1(4H)-yl)acetamide
1-ethyl-N-(2-hydroxy-5-methylphenyl)-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxamide
N-(4-bromo-2-fluorophenyl)-1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxamide
1-ethyl-N-(3-fluoro-4-methylphenyl)-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxamide
N-(5-chloro-2-hydroxyphenyl)-1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxamide
N-(2,5-difluorophenyl)-1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxamide
N-(3,4-difluorophenyl)-1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxamide

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