88897-28-3

Basic information

• Product Name: E-ethyl <(1-N-5,6-di-O-benzoyl-2-deoxy-1,3-di-N-p-tolylsulfonylstreptamin-4-yl) 3,4-di-O-benzoyl-2,6,7-trideoxy-2-p-tolylsulfonamido-α-D-gluco-oct-6-enopyranosid>uronate
• CAS NO: 88897-28-3
• Molecular Weight: 1374.53
• Mol File: 88897-28-3.mol

Chemical Properties

• CAS DataBase Reference: E-ethyl <(1-N-5,6-di-O-benzoyl-2-deoxy-1,3-di-N-p-tolylsulfonylstreptamin-4-yl) 3,4-di-O-benzoyl-2,6,7-trideoxy-2-p-tolylsulfonamido-α-D-gluco-oct-6-enopyranosid>uronate(CAS DataBase Reference)
• NIST Chemistry Reference: E-ethyl <(1-N-5,6-di-O-benzoyl-2-deoxy-1,3-di-N-p-tolylsulfonylstreptamin-4-yl) 3,4-di-O-benzoyl-2,6,7-trideoxy-2-p-tolylsulfonamido-α-D-gluco-oct-6-enopyranosid>uronate(88897-28-3)
• EPA Substance Registry System: E-ethyl <(1-N-5,6-di-O-benzoyl-2-deoxy-1,3-di-N-p-tolylsulfonylstreptamin-4-yl) 3,4-di-O-benzoyl-2,6,7-trideoxy-2-p-tolylsulfonamido-α-D-gluco-oct-6-enopyranosid>uronate(88897-28-3)

Safety Data

• Hazardous Substances Data: 88897-28-3(Hazardous Substances Data)

Upstream product

• 88897-27-2 (1-N-5,6-di-O-benzoyl-2-deoxy-1,3-di-N-p-tolylsulfonylstreptamin-4-yl) 3,4-di-O-benzoyl-2-deoxy-2-p-tolylsulfonamido-α-D-gluco-hexodialdo-1,5-pyranoside 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 

Downstream Products

• 88897-29-4 ethyl <(1-N-5,6-di-O-benzoyl-2-deoxy-1,3-di-N-p-tolylsulfonylstreptamin-4-yl) 3,4-di-O-benzoyl-2-deoxy-2-p-tolylsulfonamido-L-threo-α-D-gluco-octo-1,5-pyranosid>uronate 
• 88897-29-4 ethyl <(1-N-5,6-di-O-benzoyl-2-deoxy-1,3-di-N-p-tolylsulfonylstreptamin-4-yl) 3,4-di-O-benzoyl-2-deoxy-2-p-tolylsulfonamido-D-threo-α-D-gluco-octo-1,5-pyranosid>uronate 

Relevant articles and documents

Approach to the Pseudodisaccharides Present in (Oxy)apramycin. Synthesis of a 4-O-Amino-octodiosyl-2-deoxystreptamine from Paromamine

The synthesis of an N-protected 2'-amino-2'-deoxy-1'-O-(2-deoxystreptamin-4-yl)-α-D-threo-D-gluco-octo-1',5':4',8'-dipyranose in nine steps from paromamine is described; the key steps are the conversion of paromamine into a protected octuronic acid derivative, followed by its 8',4'-lactonization upon removal of the O-protecting groups, and partial reduction of the resulting 'trans-decalone-like' lactone.

SYNTHETIC ROUTES FROM PAROMAMINE TO THE OCTODIOSE-CONTAINING PSEUDODISACCHARIDE PRESENT IN (OXY)APRAMYCIN

The synthesis of a 4-O-(2-amino-2-deoxyoctodiosyl)-2-deoxystreptamine, the first synthetic analog of the unusual pseudodisaccharide present in (oxy)apramycin was accomplished, starting from paromamine, by a two-carbon chain-elongation and a stereoselective cis-hydroxylation of the resulting E-unsaturated octuronate to give either ethyl 3,4-di-O-benzoyl-2-deoxy-2-p-tolylsulfonamido-D-threo-α-D-gluco- (12) or -L-threo-α-D-gluco-octo-1,5-pyranosid> uronate.Mehtoxide-mediated deacylation of 12 afforded in one step a bicyclic, trans-decalone-like urono-8',4'-lactone (14) that was highly sensitive to acid-catalyzed alcoholysis and had properties in sharp contrast to those of D-glucurono-6,3-lactone.Partial reduction of lactone 14 or of the corresponding methyl octuronate 12 with lithium aluminum hydride at low temperature gave the expected α-D-threo-D-gluco-octodialdo-1,5-pyranoside-8,4-pyranose, which was methanolyzed and N-detosylated to afford the free pseudodisaccharide 1-(2-deoxystreptamin-4-yl) 8-methyl (8R,S)-2-amino-2-deoxy-α-D-threo-D-gluco-octodialdo-1,5:8,4-dipyranodioside.All of the octodiose derivatives were found to adopt a rigid, dipyranoid structure.