144539-85-5

Basic information

• Product Name: b-D-Allopyranoside,(3aS,4S,5S,6R,6aR)-2-(dimethylamino)-3a,5,6,6a-tetrahydro-4-hydroxy-6-(hydroxymethyl)-4H-cyclopentoxazol-5-yl2-(acetylamino)-4-O-[2-(acetylamino)-2-deoxy-b-D-allopyranosyl]-2-deoxy-
• Synonyms: b-D-Allopyranoside,2-(dimethylamino)-3a,5,6,6a-tetrahydro-4-hydroxy-6-(hydroxymethyl)-4H-cyclopentoxazol-5-yl2-(acetylamino)-4-O-[2-(acetylamino)-2-deoxy-b-D-allopyranosyl]-2-deoxy-, [3aS-(3aa,4a,5b,6a,6aa)]-; 4H-Cyclopentoxazole, b-D-allopyranoside deriv.; Isoallosamidin;Isoallosamidine
• CAS NO: 144539-85-5
• Molecular Formula: C25H42 N4 O14
• Molecular Weight: 622.627
• Mol File: 144539-85-5.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: b-D-Allopyranoside,(3aS,4S,5S,6R,6aR)-2-(dimethylamino)-3a,5,6,6a-tetrahydro-4-hydroxy-6-(hydroxymethyl)-4H-cyclopentoxazol-5-yl2-(acetylamino)-4-O-[2-(acetylamino)-2-deoxy-b-D-allopyranosyl]-2-deoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: b-D-Allopyranoside,(3aS,4S,5S,6R,6aR)-2-(dimethylamino)-3a,5,6,6a-tetrahydro-4-hydroxy-6-(hydroxymethyl)-4H-cyclopentoxazol-5-yl2-(acetylamino)-4-O-[2-(acetylamino)-2-deoxy-b-D-allopyranosyl]-2-deoxy-(144539-85-5)
• EPA Substance Registry System: b-D-Allopyranoside,(3aS,4S,5S,6R,6aR)-2-(dimethylamino)-3a,5,6,6a-tetrahydro-4-hydroxy-6-(hydroxymethyl)-4H-cyclopentoxazol-5-yl2-(acetylamino)-4-O-[2-(acetylamino)-2-deoxy-b-D-allopyranosyl]-2-deoxy-(144539-85-5)

Safety Data

• Hazardous Substances Data: 144539-85-5(Hazardous Substances Data)

Upstream product

• 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 
• 136773-85-8 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-allopyranose 
• 124583-64-8 (+/-)-4S-<(benzyloxy)methyl>-3aS,6aR-dihydro-2-(dimethylamino)-5R,6R-dihydroxycyclopentano<4,3-d>oxazole 
• 136800-69-6 (3aR,4S,5S,6R,6aR)-4-Acetoxy-6-<(benzyloxy)methyl>-2-(dimethylamino)-3a,5,6,6a-tetrahydro-4H-cyclopentoxazol-5-yl 2-acetamido-4-O-(2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-allopyranosyl)-3,6-di-O-benzyl-2-deoxy-β-D-allopyranoside 
• 114621-74-8 (3aR,4S,5S,6R,6aR)-4-Acetoxy-6-(acetoxymethyl)-2-(dimethylamino)-3a,5,6,6a-tetrahydro-4H-cyclopentoxazol-5-yl 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-allopyranosyl)-3,6-di-O-acetyl-2-deoxy-β-D-allopyranoside 
• 136773-88-1 (3aS,4S,5S,6R,6aR)-6-<(Benzyloxy)methyl>-2-(dimethylamino)-3a,5,6,6a-tetrahydro-4-hydroxy-4H-cyclopentoxazol-5-yl 2-acetamido-4-O-(2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-allopyranosyl)-3,6-di-O-benzyl-2-deoxy-β-D-allopyranoside 
• 1319720-24-5 C₂₉H₄₆N₄O₁₆ 

Downstream Products

• 103766-13-8 (+/-)-3aS,6aS-dihydro-5R,6S-dihydroxy-2-(dimethylamino)-4S-(hydroxymethyl)cyclopentano<4,3-d>oxazole 
• 4710-95-6 D-glucosamine hydrochloride 
• 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 

Relevant articles and documents

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.

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.

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.