105763-44-8

Basic information

• Product Name: (2R,3S)-1-(benzoyloxy)-3-phthalimido-2-O-(imidazolylthiocarbonyl)-5-hexen-2-ol
• Synonyms: (2R,3S)-1-(benzoyloxy)-3-phthalimido-2-O-(imidazolylthiocarbonyl)-5-hexen-2-ol
• CAS NO: 105763-44-8
• Molecular Weight: 475.525
• Mol File: 105763-44-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2R,3S)-1-(benzoyloxy)-3-phthalimido-2-O-(imidazolylthiocarbonyl)-5-hexen-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S)-1-(benzoyloxy)-3-phthalimido-2-O-(imidazolylthiocarbonyl)-5-hexen-2-ol(105763-44-8)
• EPA Substance Registry System: (2R,3S)-1-(benzoyloxy)-3-phthalimido-2-O-(imidazolylthiocarbonyl)-5-hexen-2-ol(105763-44-8)

Safety Data

• Hazardous Substances Data: 105763-44-8(Hazardous Substances Data)

Upstream product

• 105763-27-7 (2R,3R)-1,2-isopropylidene-3-phthalimidohex-5-ene-1,2-diol 
• 5694-71-3 2,2-Dimethyl-alpha-2-propenyl-1,3-dioxolane-4-methanol 
• 105763-43-7 (2R,3R)-1-(benzoyloxy)-3-phthalimido-5-hexen-2-ol 
• 6160-65-2 1,1'-Thiocarbonyldiimidazole 
• 105763-34-6 (2R,3R)-3-phthalimidohex-5-ene-1,2-diol 
• 98-88-4 benzoyl chloride 

Downstream Products

• 105763-45-9 (R)-3-amino-1-(benzoyloxy)-5-hexene 
• 105784-81-4 (R)-1-(benzoyloxy)-3-phthalimido-5-hexene 

Relevant articles and documents

A General and Practical Synthesis of (R)-Phthalimido Aldehydes and D-α-Amino Acids from D-Mannitol

A short and practical synthesis of five D-α-amino acids is described from D-mannitol as the chiral educt.The key steps in the sequence are (a) the erythro-selective addition of organometals to (R)-2,3-O-isopropylideneglyceralaldehyde, (b) the Mitsunobu inversion substituting N-phthalimide for hydroxyl, and (c) acetonide hydrolysis and glycol cleavage to give the N -phthaloyl-(R)-α-aminoaldehydes 7.These are oxidized under Jones conditions to give the N-protected amino acids 8.The examples investigated (alanine, aminobutyric acid, norvaline, and allyl- and vinylglycine) demonstrate the general applicability of the method.