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56180-94-0

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Purification process for manufacturing a high pure acarbose
A process for purifying and preparing highly pure acarbose from acarbose-containing fermentation broth. The acarbose is purified through steps of alcohol precipitation, a strongly acidic cation exchanger chromatography and an immobolized enzyme affinity chromatography. Acarbose is generally applied in treating diabetes.
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Page/Page column 4

(2008/06/13)

TOTAL SYNTHESIS OF ACARBOSE AND ADIPOSIN-2
The first total synthesis is described of the α-D-glucosidase inhibitor acarbose (1a). 1,6-Anhydro-4'-O-(3,4-anhydro-6-deoxy-α-D-galactopyranosyl)-β-maltose (21), prepared from 1,6-β-maltotriose (3a), and (+)-4,7:5,6-di-O-isopropilydenevalienamine (28) gave two pseudo-tetrasaccharide derivatives separable as the per-O-acetyl derivatives (29 and 31) by chromatography, and their structures were established on the basis of 1H-n.m.r. spectroscopy.On acetolysis followed by acetylation, 29 afforded the peracetate (1b), which was O-deacetylated to give 1a.Likewise, adiposin-2 (2a), the 6''-hydroxy analogue of 1a, isolated from fermentation broth of Streptomyces calvus TM-521, was synthesised.
Shibata, Yasushi,Ogawa, Seiichiro
p. 309 - 322
(2007/10/02)

Total Synthesis of Acarbose and Adiposin-2
The first complete synthesis of acarbose (1a), the pseudotetrasaccharidic α-amylase inhibitor, is reported: coupling of the protected (+)-valienamine (16) and the epoxide (9) derived from 1'',6''-anhydromaltotriose (3), followed by deprotection; likewise, adiposin-2 (2a), the 6'-hydroxy analogue of (1a), has also been synthesised.
Ogawa, Seiichiro,Shibata, Yasushi
p. 605 - 606
(2007/10/02)

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Chemical Properties

Appearance/Colour :Off-white solid
Melting Point: 165-170 °C
Boiling Point: 971.6 °C at 760 mmHg
Flash Point:541.4 °C
Density: 1.74 g/cm³
Solubility:Very soluble in water, soluble in methanol, practically insoluble in methylene chloride.
Storage Temp.:Store at RT
Vapor Pressure: 0mmHg at 25°C
Refractive Index: 1.689
PKA: 12.39±0.20(Predicted)
Merck: 14,18
PSA: 321.17000
LogP: -8.17360

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