176389-19-8

Basic information

• Product Name: Acetic acid (1S,2R,5R,6S)-5,6-diacetoxy-2-((3aR,4S,6R,7R,7aS)-7-acetoxy-4-acetoxymethyl-6-bromo-2-oxo-tetrahydro-pyrano[3,4-d]oxazol-3-yl)-4-acetoxymethyl-cyclohex-3-enyl ester
• Synonyms: Acetic acid (1S,2R,5R,6S)-5,6-diacetoxy-2-((3aR,4S,6R,7R,7aS)-7-acetoxy-4-acetoxymethyl-6-bromo-2-oxo-tetrahydro-pyrano[3,4-d]oxazol-3-yl)-4-acetoxymethyl-cyclohex-3-enyl ester
• CAS NO: 176389-19-8
• Molecular Weight: 678.442
• Mol File: 176389-19-8.mol

Chemical Properties

• CAS DataBase Reference: Acetic acid (1S,2R,5R,6S)-5,6-diacetoxy-2-((3aR,4S,6R,7R,7aS)-7-acetoxy-4-acetoxymethyl-6-bromo-2-oxo-tetrahydro-pyrano[3,4-d]oxazol-3-yl)-4-acetoxymethyl-cyclohex-3-enyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Acetic acid (1S,2R,5R,6S)-5,6-diacetoxy-2-((3aR,4S,6R,7R,7aS)-7-acetoxy-4-acetoxymethyl-6-bromo-2-oxo-tetrahydro-pyrano[3,4-d]oxazol-3-yl)-4-acetoxymethyl-cyclohex-3-enyl ester(176389-19-8)
• EPA Substance Registry System: Acetic acid (1S,2R,5R,6S)-5,6-diacetoxy-2-((3aR,4S,6R,7R,7aS)-7-acetoxy-4-acetoxymethyl-6-bromo-2-oxo-tetrahydro-pyrano[3,4-d]oxazol-3-yl)-4-acetoxymethyl-cyclohex-3-enyl ester(176389-19-8)

Safety Data

• Hazardous Substances Data: 176389-19-8(Hazardous Substances Data)

Upstream product

• 190446-28-7 Acetic acid (3aR,4S,7R,7aS)-6-acetoxy-4-acetoxymethyl-2-oxo-3-((1R,4R,5S,6S)-4,5,6-triacetoxy-3-acetoxymethyl-cyclohex-2-enyl)-hexahydro-pyrano[3,4-d]oxazol-7-yl ester 
• 176389-17-6 Acetic acid (1S,2R,6S,7R,8R)-4-oxo-3-((1R,4R,5S,6S)-4,5,6-triacetoxy-3-acetoxymethyl-cyclohex-2-enyl)-5,9,11-trioxa-3-aza-tricyclo[6.2.1.0^2,6]undec-7-yl ester 

Downstream Products

• 176389-20-1 Acetic acid (3aR,4S,6S,7R,7aS)-4-acetoxymethyl-2-oxo-6-phenylsulfanyl-3-((1R,4R,5S,6S)-4,5,6-triacetoxy-3-acetoxymethyl-cyclohex-2-enyl)-hexahydro-pyrano[3,4-d]oxazol-7-yl ester 
• 190784-97-5 methyl 4-deoxy-4-[(1'R,4'R,5'S,6'S)-4',5',6'-trihydroxy-3'-(hydroxymethyl)cyclohex-2'-enyl]amino-β-D-glucopyranoside 
• 176389-21-2 benzyl O-<2,3-di-O-acetyl-3,4-O,N-carbonyl-4-deoxy-4-<(1R,4R,5S,6S)-4,5,6-triacetoxy-3-(acetoxymethyl)-cyclohex-2-enyl>amino-β-D-glucopyranosyl>-(1->4)-O-(tri-O-benzyl-β-D-glucopyranosyl)-(1->4)-tri-O-benzyl-β-D-glucopyranoside 

Relevant articles and documents

β-acarbose. V * the synthesis of a hydroxylated derivative of a diastereoisomer of methyl acarviosin

The treatment of a 1-epivalienamine derivative with 1,6:3,4-dianhydro-2-O-benzyl-β-D-galactose has given an amino alcohol capable of conversion into either a cyclic carbamate or an aziridine. All attempts at acetolysis of the 1,6-anhydro ring of the cyclic carbamate failed owing to the inherent reactivity of the (allylic) benzyl ethers present in the molecule. Therefore, following a reduction with lithium in ammonia and acetylation of the product, a new cyclic carbamate was obtained which underwent successful acetolysis to provide a heptaacetate. This heptaacetate could be transformed into the desired methyl β-D-glucoside and base hydrolysis provided the 6-hydroxylated derivative of a diastereoisomer of methyl acarviosin, a putative inhibitor of enzymes which process β-D-glucosidic linkages.

'β-Acarbose': A potential inhibitor of β-D-glucosidases and β-D-glucan hydrolases

'β-Adiposin-2', the 6''-hydroxylated derivative of 'β-acarbose', itself a diastereoisomer of the naturally occurring acarbose, has been prepared from a 1-epivalienamine derivative, 1,6:3,4-dianhydro-2-O-benzyl-β-D-galactose and benzyl 2,3,6,2',3',6'-hexo-O-benzyl-β-cellobioside.