183988-91-2

Basic information

• Product Name: (3aR,4S,5S,6S,6aR)-6-Benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-2-dimethylamino-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-5-ol
• Synonyms: (3aR,4S,5S,6S,6aR)-6-Benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-2-dimethylamino-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-5-ol
• CAS NO: 183988-91-2
• Molecular Weight: 420.624
• Mol File: 183988-91-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (3aR,4S,5S,6S,6aR)-6-Benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-2-dimethylamino-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-5-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (3aR,4S,5S,6S,6aR)-6-Benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-2-dimethylamino-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-5-ol(183988-91-2)
• EPA Substance Registry System: (3aR,4S,5S,6S,6aR)-6-Benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-2-dimethylamino-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-5-ol(183988-91-2)

Safety Data

• Hazardous Substances Data: 183988-91-2(Hazardous Substances Data)

Upstream product

• 100021-11-2 (1α,2β,3α)-2-(benzyloxymethyl)cyclopent-4-ene-1,3-diol 
• 134756-62-0 <1(S)-(1α,4α,5β)>-4-(acetyloxy)-5-<(benzyloxy)methyl>-2-cyclopenten-1-ol 
• 134756-61-9 (1α,2β,3α)-2-<(benzyloxy)methyl>-4-cyclopentene-1,3-diol diacetate 
• 184179-65-5 (3aS,4S,5S,6S,6aR)-6-Benzyloxymethyl-2-dimethylamino-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazole-4,5-diol 
• 184179-67-7 ((1aR,1bR,4aR,5R,5aS)-5-Benzyloxymethyl-1b,4a,5,5a-tetrahydro-1aH-1,4-dioxa-2-aza-cyclopropa[a]pentalen-3-yl)-dimethyl-amine 
• 184179-61-1 Carbamic acid (1S,4R,5S)-5-benzyloxymethyl-4-hydroxy-cyclopent-2-enyl ester 
• 184179-64-4 ((3aS,6R,6aR)-6-Benzyloxymethyl-6,6a-dihydro-3aH-cyclopentaoxazol-2-yl)-dimethyl-amine 
• 184179-63-3 (3aS,6R,6aR)-6-Benzyloxymethyl-3,3a,6,6a-tetrahydro-cyclopentaoxazol-2-one 
• 183988-89-8 Acetic acid (3aS,4S,5S,6R,6aR)-6-benzyloxymethyl-2-dimethylamino-4-hydroxy-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-5-yl ester 
• 183988-90-1 Acetic acid (3aR,4S,5S,6R,6aR)-6-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-2-dimethylamino-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-5-yl ester 

Downstream Products

• 183988-93-4 C₇₃H₉₆N₄O₁₇S₂Si₂ 
• 183988-92-3 C₇₃H₉₆N₄O₁₇S₂Si₂ 

Relevant articles and documents

The total synthesis of allosamidin. Expansions of the methodology of azaglycosylation pursuant to the total synthesis of allosamidin. A surprising enantiotopic sense for a lipase-induced deacetylation

Allosamidin, recently isolated from mycelial extracts of Streptomyces sp. 1713, is a powerful and selective chitinase inhibitor. The total synthesis of allosamidin is described herein. The electric eel acetylcholinesterase-mediated enantioselective hydrolysis of (trans,trans)-2-(benzyloxy)cyclopentene-1,3-diol diacetate accessed a monoacetyl derivative. Five additional steps produced a protected version of the aglycon ('allosamizoline') sector of allosamidin. An allal derivative stereoselectively reacted with benzenesulfonamide in the presence of a halonium source to afford a 2β-halo-1α-sulfonamidohexose. Treatment of this product with a strong base generated an intermediate 1,2-sulfonylaziridine, which was trapped with a protected allal derivative to provide a disaccharide glycal. Reiteration of this scheme gave access to the required trisaccharide. Following deprotection, the total synthesis of allosamidin was accomplished. In addition, the method, with modification, gave access to several allosamidin analogs.