103766-13-8

Basic information

• Product Name: 4H-Cyclopentoxazole-4,5-diol, 2-(dimethylamino)-3a,5,6,6a-tetrahydro-6-(hydroxymethyl)-, (3aR,4R,5R,6R,6aS)-
• Synonyms: 4H-Cyclopentoxazole-4,5-diol, 2-(dimethylamino)-3a,5,6,6a-tetrahydro-6-(hydroxymethyl)-, (3aR,4R,5R,6R,6aS)-
• CAS NO: 103766-13-8
• Molecular Formula: C9H16 N2 O4
• Molecular Weight: 216.23
• Mol File: 103766-13-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4H-Cyclopentoxazole-4,5-diol, 2-(dimethylamino)-3a,5,6,6a-tetrahydro-6-(hydroxymethyl)-, (3aR,4R,5R,6R,6aS)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-Cyclopentoxazole-4,5-diol, 2-(dimethylamino)-3a,5,6,6a-tetrahydro-6-(hydroxymethyl)-, (3aR,4R,5R,6R,6aS)-(103766-13-8)
• EPA Substance Registry System: 4H-Cyclopentoxazole-4,5-diol, 2-(dimethylamino)-3a,5,6,6a-tetrahydro-6-(hydroxymethyl)-, (3aR,4R,5R,6R,6aS)-(103766-13-8)

Safety Data

• Hazardous Substances Data: 103766-13-8(Hazardous Substances Data)

Upstream product

• 124583-64-8 (+/-)-4S-<(benzyloxy)methyl>-3aS,6aR-dihydro-2-(dimethylamino)-5R,6R-dihydroxycyclopentano<4,3-d>oxazole 
• 124648-55-1 (3aS,4R,5S,6S,6aR)-6-Benzyloxymethyl-2-dimethylamino-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazole-4,5-diol; compound with trifluoro-acetic acid 
• 124583-64-8 (1S,5R)-8-exo-benzyloxymethyl-3-dimethylamino-6-exo,7-endo-dihydroxy-2-oxa-4-azabicyclo<3.3.0>octan-3-ene 
• 165375-20-2 (1R,2R,3S,4S,5S)-3-(ethoxycarbonylamino)-4-hydroxy-5-(hydroxymethyl)cyclo-pentane-1,2-diyl dibenzoate 
• 1001670-99-0 C₁₃H₂₄N₂O₆ 
• 154017-99-9 methyl 2,6-dideoxy-6-iodo-2-phthalimido-3,4-tetraisopropyldisiloxylidene-D-glucopyranoside 
• 154018-02-7 2-aza-3-oxa-8-phthalimido-6,7-tetraisopropyldisiloxylidenedioxybicyclo<3.3.0>oct-1-ene 
• 154017-98-8 methyl 2-deoxy-2-phthalimido-6-O-p-toluenesulfonyl-D-glucopyranoside 
• 138395-69-4 2-aza-6,7-di-t-butyldimethylsiloxy-3-oxa-8-phthalimidobicyclo<3.3.0>oct-1-ene 
• 138395-70-7 2-[(1R,2R,3R,4R)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-4-hydroxymethyl-5-oxo-cyclopentyl]-isoindole-1,3-dione 
• 138395-71-8 2,3-di-t-butyldimethylsiloxy-5-hydroxy-4-phthalimidocyclopentanemethanol 
• 138395-72-9 2-aza-7,8-di-t-butyldimethylsiloxy-6-hydroxymethyl-4-oxabicyclo<3.3.0>octan-3-one 
• 80675-64-5 (3R,4R,5R)-3,4-dibenzoyloxy-5-(hydroxymethyl)cyclopent-1-ene 
• 138395-73-0 (3aS,4R,5R,6S,6aS)-6-(Acetoxymethyl)-2-oxohexahydro-2H-cyclopenta[d]oxazole-4,5-diyl diacetate 

Downstream Products

• 186041-00-9 2-[(4aR,6R,7R,8S,8aS)-8-Benzyloxy-6-((3aS,4R,5R,6R,6aS)-6-benzyloxymethyl-2-dimethylamino-5-hydroxy-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-4-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-isoindole-1,3-dione 

Relevant articles and documents

TOTAL SYNTHESIS OF (+/-)-ALLOSAMIZOLINE FROM A SYMMETRIC TRISUBSTITUTED CYCLOPENTENE

A convergent synthesis of the aminocyclitol allosamizoline 1, which is found in a class of pseudotrisaccharide chitinase inhibitors known as the allosamidins, is reported.

A concise and efficient synthesis of (-)-allosamizoline

A regio- and stereocontrolled total synthesis of (-)-allosamizoline is described. The key steps for this synthesis are ring-closing metathesis to form the cyclopentene core, halocyclization to afford the oxazoline ring, and finally stereoselective alkene radical addition followed by an alkene isomerization reaction to install the hydroxymethyl group. (-)-Allosamizoline was prepared in a total of 13 steps and 22% overall yield.

Chemo-enzymatic synthesis of tetra-N-acetyl-chitotetraosyl allosamizoline

A new compound 7, possessing a tetra-N-acetyl-chitotetraosyl moiety as a constituent, was synthesized by bacterial fermentation which used allosamizoline 6 as the initial acceptor.

Preparation of 3,6-di-O-benzylallosamizoline from natural allosamidin

Preparation of 3,6-di-O-benzylallosamizoline, the aglycon required for the total synthesis of allosamidin and its related compounds, from natural allosamizoline obtained from natural allosamidin is described. Copyright (C) 2000 Elsevier Science Ltd.

Synthesis of allosamidin analogues

Two new isomers of allosamidin and allosamizoline, and two dimeric allosamidin analogues have been synthesized. The new compounds have been tested for inhibition of insect chitinase and for toxicity to insect larvae.

Syntheses of the Fungicide/Insecticide Allosamidin and a Structural Isomer

A synthesis of the naturally occurring inhibitor of chitin metabolism, allosamidin 1, involves, as the key step, condensation between the allosamizoline derivative 39, prepared following oxyamination of the cyclopentene 19, and the disaccharide glycosylating agent 54 which was synthesised from 2-acetamido-2-deoxy-D-glucose.The structural isomer 59 of allosamidin is also reported.Brief biological test results obtained using isomers 1 and 59 are recorded.

Synthesis of (-)-Allosamizoline, the Pseudoaminosugar Moiety of Allosamidin, a Chitinase Inhibitor

The enantioselective synthesis of (-)-allosamizoline (2a), the aminocyclitol moiety of allosamidin (1a), was achieved by starting from D-glucosamine (3).Intramolecular nitrile oxide cycloaddition was adopted as the key step to construct a functional cyclo

A general synthetic strategy toward aminocyclopentitol glycosidase inhibitors. Application of palladium catalysis to the synthesis of allosamizoline and mannostatin A

A general strategy for the synthesis of aminocyclopentitol glycosidase inhibitors has been applied to the synthesis of allosamizoline and mannostatin A. These cyclic pseudosugars are members of a growing family of highly potent and selective glycosidase i

THE STRUCTURE OF ALLOSAMIDIN, A NOVEL INSECT CHITINASE INHIBITOR, PRODUCED BY STREPTOMYCES SP.

Allosamidin (1), a novel insect chitinase inhibitor, was isolated from the mycelium of Streptomyces sp. and characterized as 1, which was a basic pseudotrisaccharide consisting of 2-acetamido-2-deoxy-D-allose (N-acetyl-D-allosamine) and a novel aminocyclitol derivative(3), termed allosamizoline.