153322-50-0

Upstream product

• 2280-44-6 D-Glucose 
• 139573-30-1 [(3aS,4R,5R,6S,6aS)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-dimethylamino-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-6-yl]-methanol 
• 134756-66-4 3,6-di-O-benzyl-(-)-allosamizoline 
• 153213-92-4 phenyl 3,6-di-O-acetyl-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 
• 136773-80-3 Allyl 3-O-benzyl-4,6-O-benzylidene-2-<2-(benzyloxycarbonyl)benzamido>-2-deoxy-α-D-allopyranoside 
• 136845-45-9 Allyl 4,6-O-benzylidene-2-(2-carboxybenzamido)-2-deoxy-α-D-allopyranoside 
• 136773-78-9 Allyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(methanesulfonyl)-D-glucopyranoside 
• 136845-44-8 Allyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-allopyranoside 
• 136773-79-0 Allyl 2-Amino-4,6-O-benzylidene-2-deoxy-α-D-allopyranoside 
• 136773-87-0 (3aS,4S,5S,6R,6aR)-6-<(Benzyloxy)methyl>-2-(dimethylamino)-3a,5,6,6a-tetrahydro-4-hydroxy-4H-cyclopentoxazol-5-yl 3,6-di-O-benzyl-4-O-(3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-allopyranosyl)-2-deoxy-2-phthalimido-β-D-allopyranoside 

Downstream Products

• 115699-20-2 (1S,5R)-3-dimethylamino-6-exo-hydroxy-8-exo-hydroxymethyl-2-oxa-4-azabicyclo<3.3.0>oct-3-en-7-endo-yl 2-acetamido-2-deoxy-β-D-allopyranoside 
• 103766-13-8 (+/-)-3aS,6aS-dihydro-5R,6S-dihydroxy-2-(dimethylamino)-4S-(hydroxymethyl)cyclopentano<4,3-d>oxazole 
• 4710-95-6 D-glucosamine hydrochloride 

Relevant academic research and scientific papers

Synthesis of a new allosamidin analog, N,N'-diacetyl-beta-chitobiosyl allosamizoline and its inhibitory activity against some chitinases.

A new allosamidin analog (2), possessing an N',N'-diacetylchitobiosyl moiety as a constituent, was stereoselectively synthesized through the coupling reaction between the disaccharide thioglycoside derivative (5) and allosamizoline derivative (6). The inhibitory activity of 2 against chitinases derived from an insect, yeast and mold were tested and compared with that of allosamidin (1).

Syntheses and activity of carbohydrate-containing chitinase inhibitors

The pseudo-Trisaccharide allosamidin 1 is a potent inhibitor of all family 18 chitinases, and it is confirmed to have insecticidal and antifungal activities. However, the synthesis of allosamidins is very difficult, and it is a challengeable subject. Allosamidins were synthesized in solid/liquid phase and total solid phase, respectively. Solid/liquid-phase method realizes the partial solid-phase synthesis of allosamidins. Total solid-phase method greatly simplifies the purification process. Moreover, it indicated that the inhibitory activity of N,N'-diacetyl-β-chitobiosylallosamizoline 9 against chitinase from Bombyx mori was a little weaker than that of allosamidin 1.

High-efficiency synthesis of N,N'-diacetyl-β-chitobiosyl allosamizoline

The high-efficiency synthesis of N,N'-diacetyl-β-chitobiosyl allosamizoline 2 was investigated. The Nbenzyloxycarbonyl (Cbz) protected trichloroacetimidate donors 11 and 13 were synthesized by routine method. The solidphase synthesis was performed using p

An efficient synthesis of allosamidin

The solid-phase synthesis of allosamidin was investigated. After two N-benzyloxycarbonyl (Cbz)-protected trichloroacetimidate donors were synthesized, the solid-phase synthesis was performed using polystyrene as support and an o-nitrobenzyl ether tether as linker. The target allosamidin was efficiently obtained by iterative glycosylation reactions, catalytic hydrogenation, acetylation, deacetylation, and photolysis.

Solid-phase synthesis of di-N-acetyl-β-chitobiosyl allosamizoline

The solid-phase synthesis of di-N-acetyl-β-chitobiosyl allosamizoline 2 was reported. After the 6-O-benzyl allosamizoline 16, NHCbz trichloroacetimidate donors 7, and 14 were synthesized; solid-phase synthesis was performed using the Wang resin as support. The target di-N-acetyl-β- chitobiosyl allosamizoline 2 was obtained by iterative glycosylation reactions, catalytic hydrogenation, acetylation, and deacetylation, respectively.

Solid-phase synthesis of allosamidin

The solid-phase synthesis of allosamidin is described. After the NHCbz trichloroacetimidate donors were synthesized, solid-phase synthesis was performed using the Wang resin as support. The target allosamidin was obtained by iterative glycosylation reactions, catalytic hydrogenation, acetylation, and deacetylation, respectively. Georg Thieme Verlag Stuttgart New York.

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.

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 Allosamidin

The previously prepared disaccharide 2 was deprotected (-> 3) and transformed into the trichloroacetimidate 4.In the presence of Me3SiOTf, 4 reacted regioselectively with the racemic allosamizoline benzyl ether 5, to yield (61 percent) the pseudotrisaccharides 7-10 (44:40:9:7) and the elimination product 6 (Scheme 1).Selective dephthaloylation (MeNH2, MeOH) of 7 and 8, followed by acetylation, gave 12 (73 percent) and 13 (74 percent), respectively (Scheme 2); harsher conditions (NH2NH2*H2O, EtOH, reflux), followed by acetylation, transformed 7 into 11.Deacetylation of 11-13 yielded 14-16, respectively.Allosamidin (1) was obtained in high yield by hydrogenation of 15 under acidic conditions (Scheme 3).Similarly, 16 and 14 were transformed into 17 and 18, respectively.Preliminary data on the inhibition of endochitinases by 1 and 17 are reported.

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).