134756-66-4

Upstream product

• 100-39-0 benzyl bromide 
• 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 
• 252055-28-0 3-O-benzylallosamizoline 
• 252055-27-9 [3aR-(3aα,4αb,5β,6α,6aα)]-4,5-dihydroxy-hexahydro-6-(hydroxymethyl)-2H-cyclopentoxazol-2-thione 
• 100021-11-2 (1α,2β,3α)-2-(benzyloxymethyl)cyclopent-4-ene-1,3-diol 
• 134875-85-7 <3a(R)-(3aα,6α,6aα)>-6-<(benzyloxy)methyl>-3,3a,6,6a-tetrahydro-2H-cyclopentoxazol-2-one 
• 134756-62-0 <1(S)-(1α,4α,5β)>-4-(acetyloxy)-5-<(benzyloxy)methyl>-2-cyclopenten-1-ol 
• 134875-87-9 <3a(R)-(3aα,6α,6aα)>-6-<(benzyloxy)methyl>-3,6a-dihydro-N,N-dimethyl-6H-cyclopentoxazol-2-amine 
• 134756-65-3 <1(R)-(1α,2β,3α)>-2-<(benzyloxy)methyl>-4-cyclopentene-1,3-diol monocarbamate 
• 134756-63-1 <1(R)-(1α,4α,5β)>-5-<(benzyloxy)methyl>-4-<(tert-butyldimethylsilyl)oxy>-2-cyclopenten-1-ol 
• 134756-61-9 (1α,2β,3α)-2-<(benzyloxy)methyl>-4-cyclopentene-1,3-diol diacetate 
• 174810-43-6 Acetic acid (1R,4S,5S)-5-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-cyclopent-2-enyl ester 
• 134756-64-2 <1(R)-(1α,4α,5β)>-5-<(benzyloxy)methyl>-4-<(tert-butyldimethylsilyl)oxy>-2-cyclopenten-1-ol carbamate 
• 81927-55-1 O-benzyl 2,2,2-trichloroacetimidate 

Downstream Products

• 134756-69-7 O-<2-benzenesulfonamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-D-allopyranosyl>-β-(1->4)-O-<2-benzenesulfonamido-6-O-benzyl-2-deoxy-3-O-<<2-(trimethylsilyl)ethoxy>methyl>-D-allopyranosyl>-β-(1->4)-3,6-di-O-benzyl-(-)-allosamizoline 
• 144539-85-5 allosamidin 

Relevant academic research and scientific papers

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.

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.

Total synthesis of (-)-allosamidin, an insect chitinase inhibitor, employing chitin as a key starting material

(-)-Allosamidin (1), a novel insect chitinase inhibitor, was stereoselectively synthesized from di- and monosaccharidic constituents of chitin, N,N'-diacetylchitobiose (2) and D-glucosamine (3).