20196-70-7

Basic information

• Product Name: (+)-(R)-2,3-bis(benzyloxy)propanal
• Synonyms: (+)-(R)-2,3-bis(benzyloxy)propanal
• CAS NO: 20196-70-7
• Molecular Weight: 270.328
• Mol File: 20196-70-7.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: (+)-(R)-2,3-bis(benzyloxy)propanal(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-(R)-2,3-bis(benzyloxy)propanal(20196-70-7)
• EPA Substance Registry System: (+)-(R)-2,3-bis(benzyloxy)propanal(20196-70-7)

Safety Data

• Hazardous Substances Data: 20196-70-7(Hazardous Substances Data)

Upstream product

• 100-44-7 benzyl chloride 
• 3969-84-4 3,4-di-O-isopropylidene-D-mannitol 
• 3427-24-5 (2S,3E,5S)-1,2,5,6-tetrahydroxy-1,2:5,6-di-O-isopropylidene-hex-3-ene 
• 100-39-0 benzyl bromide 
• 20258-50-8 1,2,5,6-tetra-O-benzyl-3,4-O-isopropylidene-D-mannitol 
• 628690-03-9 1,2,5,6-tetra-O-benzyl-D-sorbitol 
• 926318-95-8 C₃₂H₃₈O₅ 
• 926318-94-7 C₂₅H₃₂O₅ 
• 926318-83-4 C₂₇H₃₆O₆ 
• 926318-96-9 C₂₉H₃₄O₅ 
• 20196-69-4 1,2,5,6-tetra-O-benzyl-D-mannitol 

Downstream Products

• 158719-47-2 (4S,5R)-5-((R)-1,2-Bis-benzyloxy-ethyl)-2-(4-methoxy-phenyl)-4,5-dihydro-oxazole-4-carboxylic acid methyl ester 
• 106863-84-7 (2S,6S)-2-((R)-1,2-Bis-benzyloxy-ethyl)-6-methoxy-3,6-dihydro-2H-pyran 
• 106824-35-5 (2S,6R)-2-((R)-1,2-Bis-benzyloxy-ethyl)-6-methoxy-3,6-dihydro-2H-pyran 
• 106863-86-9 (2R,6S)-2-((R)-1,2-Bis-benzyloxy-ethyl)-6-methoxy-3,6-dihydro-2H-pyran 
• 106863-85-8 (2R,6R)-2-((R)-1,2-Bis-benzyloxy-ethyl)-6-methoxy-3,6-dihydro-2H-pyran 
• 112980-44-6 (R)-ethyl-4,5-dibenzyloxy-2-(Z)-pentenoate 
• 112980-44-6 (R)-ethyl-4,5-dibenzyloxy-2-(E)-pentenoate 
• 146397-39-9 (2R,3R,4R)-1,2-Bis-benzyloxy-4-((R)-5-methyl-cyclohex-1-enyl)-pentan-3-ol 
• 141692-76-4 (2R,3R)-1,2-bis(benzyloxy)hex-5-en-3-ol 
• 141692-77-5 (2R,3S)-1,2-bis(benzyloxy)hex-5-en-3-ol 
• 175730-14-0 Benzyl-[(S)-2,3-bis-benzyloxy-prop-(Z)-ylidene]-amine 
• 238401-87-1 (R)-2,3-di-O-benzylglyceraldehyde N-benzylimine 
• 238401-88-2 (R)-2,3-diO-dibenzylglyceraldehyde (S)-α-methylbenzylimine 
• 238401-90-6 (R)-2,3-di-O-benzylglyceraldehyde (R)-α-methylbenzylimine 

Relevant articles and documents

Diastereoselective Construction of the 6-Oxa-2-azabicyclo[3.2.1]octane Scaffold from Chiral α-Hydroxyaldehyde Derivatives by the Aza-Prins Reaction

(R)-2,3-Di-O-benzylglyceraldehyde and N-tosyl homoallylamine undergo aza-Prins cyclization to afford (1R,5S,7S)-7-[(benzyloxy)methyl]-2-tosyl-6-oxa-2-azabicyclo[3.2.1]octane in a highly diastereoselective manner through an unexpected intramolecular nucleophilic attack. Our work has opened a new route toward the asymmetric synthesis of 7-(alkyl or aryl)-6-oxa-2-azabicyclo[3.2.1]octane derivatives from chiral α-hydroxyaldehyde derivatives in one step.

A cross-metathesis approach to the stereocontrolled synthesis of the AB ring segment of ciguatoxin

Synthesis of the AB ring segments of ciguatoxin is described. The present synthesis includes a Lewis acid mediated cyclization of allylstannane with aldehyde, cross-metathesis reaction introducing the side chain, and Grieco-Nishizawa dehydration on the A ring.

Total synthesis of (-)-Pramanicin

The total synthesis of natural (-)-pramanicin, a highly oxygenated γlactam-type antifungal agent, is described. The enantiospecific total synthesis of this natural product commenced with 5-deoxy-1,2-O-isopropylidene-α-d-xylofuranose as an enantiopure star