131319-74-9

Basic information

• Product Name: (R)-2,3-di-O-isoproylideneglyceraldehyde N-benzylimine
• Synonyms: (R)-2,3-di-O-isoproylideneglyceraldehyde N-benzylimine
• CAS NO: 131319-74-9
• Molecular Weight: 219.283
• Mol File: 131319-74-9.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: (R)-2,3-di-O-isoproylideneglyceraldehyde N-benzylimine(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2,3-di-O-isoproylideneglyceraldehyde N-benzylimine(131319-74-9)
• EPA Substance Registry System: (R)-2,3-di-O-isoproylideneglyceraldehyde N-benzylimine(131319-74-9)

Safety Data

• Hazardous Substances Data: 131319-74-9(Hazardous Substances Data)

Upstream product

• 100-46-9 benzylamine 
• 1707-77-3 1,2:5,6-di-O-isopropylidene-D-mannitol 
• 15186-48-8 2,3-isopropylidene-glyceraldehyde 

Downstream Products

• 109208-40-4 N-benzyl-N-amine 
• 150949-66-9 (+)-(3R,4R)-cis-1-benzyl-3-benzyloxy-4-formyl-2-azetidinone 
• 153472-33-4 (3R,4R)-N-Benzyl-3-phenoxy-4-formylazetidin-2-one 
• 277331-22-3 (+)-(3R,4S)-cis-1-benzyl-3-benzyloxy-4-[(S)-1',2'-dihydroxyethyl]-2-azetidinone 
• 131196-42-4 phenyl (2S*,3S*)-benzyl<3-<1-<(tert-butyldiphenylsilyl)oxy>-2-methoxymethoxy-4-hexenyl>>carbamate 
• 131196-41-3 phenyl (2S*,3S*)-benzyl<3-<1-<(tert-butyldiphenylsilyl)oxy>-2-hydroxy-4-hexenyl>>carbamate 
• 131196-37-7 phenyl (1R*,2S*,4S*)-benzyl<1-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-(trimethylsilyl)-3-butenyl>carbamate 
• 131196-38-8 phenyl (2S*,3S*)-benzyl<3-(1,2-dihydroxy-4-hexenyl)>carbamate 
• 131196-43-5 (4S*,5S*)-3-benzyl-5-<(methoxymethyl)oxy>-4-((E)-1'-propenyl)perhydro-1,3-oxazin-2-one 
• 131196-54-8 (1R*,2S*,4S*)-N-benzyl-N-methyl-1-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-(trimethylsilyl)-3-butenylamine 
• 131196-39-9 (4S*,5S*)-3-benzyl-5-(hydroxymethyl)-4-((E)-1'-propenyl)-1,3-oxazolidin-2-one 
• 131196-40-2 (4S*,5S*)-3-benzyl-5-(hydroxymethyl)-4-((E)-1'-propenyl)-perhydro-1,3-oxazin-2-one 
• 140193-70-0 1-O-trimethylsilyl-5-(N-benzyl-N-benzoxycarbonylamino)-2,3;6,7-di-O-isopropylidene-D-glycero-D-allo-heptofuranose 
• 140193-69-7 5-(N-benzyl-N-benzoxycarbonylamino)-2,3;5,6-di-O-isopropylidene-5-deoxy-D-glycero-D-allo-heptono-1,4-lactone 

Relevant articles and documents

Crude D-(+)-Glyceraldehyde Obtained from D-Mannitol-Diacetonide by Oxidative Cleavage with Sodium Periodate: Its Reactions with Nucleophilic Species

The oxidative cleavage of D-(+)-mannitol-diacetonide with sodium periodate lead to a mixture of D-(+)-glyceraldehyde, its hydrate and oligomeric derivatives. In spite of the low concentration of free glyceraldehyde (estimated in ～20%, by NMR), good yields were obtained in nucleophilic additions involving this mixture and a variety of nucleophiles (amines, phosphonates, phosphoranes, nitronates, organometallic compounds).

N,Se-Acetals: Preparation and Use in Diastereoselective Radical Reactions

A new facile synthesis of N,S- and N,Se-acetals starting from aldehydes and primary amines is presented (Schemes 3-5). These acetals are used as precursors for stereoselective radical deuteration and allylation reactions (Schemes 6 and 7, Tables 1 and 2). The stereochemical outcome of the reactions depends on the radical trap and the substituents at the N-atom. Deuterations give always anti products with moderate to high selectivities. The allylation reactions give either syn or anti products with low to moderate selectivities. The observed stereoselectivities can be explained with a model based on minimization of A1,3 strain and are controlled by steric and stereoelectronic effects.

A straightforward synthesis of L-isoserinal

A convenient preparation of L-isoserinal 3 in six steps and 32.8% overall yield employing D-glyceraldehyde acetonide I as starting material is described. The procedure is inexpensive, easily scaled up and proceeds without observable racemization.