156045-80-6

Basic information

• Product Name: (2R,5R,6S)-6-tert-butyldimethylsiloxy-3-oxa-2-phenyl-1-azabicyclo<3.3.0>octane-8-one
• Synonyms: (2R,5R,6S)-6-tert-butyldimethylsiloxy-3-oxa-2-phenyl-1-azabicyclo<3.3.0>octane-8-one
• CAS NO: 156045-80-6
• Molecular Weight: 333.503
• Mol File: 156045-80-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2R,5R,6S)-6-tert-butyldimethylsiloxy-3-oxa-2-phenyl-1-azabicyclo<3.3.0>octane-8-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,5R,6S)-6-tert-butyldimethylsiloxy-3-oxa-2-phenyl-1-azabicyclo<3.3.0>octane-8-one(156045-80-6)
• EPA Substance Registry System: (2R,5R,6S)-6-tert-butyldimethylsiloxy-3-oxa-2-phenyl-1-azabicyclo<3.3.0>octane-8-one(156045-80-6)

Safety Data

• Hazardous Substances Data: 156045-80-6(Hazardous Substances Data)

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 156045-79-3 bicyclic (2R,5R,6R)-6-hydroxy-2-phenyl-3-oxa-1-azabicyclo<3.3.0>octan-8-one 
• 154631-82-0 (2R,5R,6R,7R)-6,7-epoxy-2-phenyl-3-oxa-1-aza-bicyclo<3.3.0>octane-8-one 
• 103201-79-2 (3R,7aS)-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one 
• 134107-65-6 (3R,7aS)-3-phenyl-3,7a-dihydro-1H-pyrrolo[1,2-c]oxazol-5-one 

Downstream Products

• 4298-08-2 trans-3-hydroxy-L-proline 

Relevant articles and documents

Chiral Pool Synthesis of trans-(2S,3S)-3-Hydroxyproline and Castanodiol from S-Pyroglutamic Acid.

The Pyroglutamic acid derivative 1 was converted through several steps into Castanodiol 9 and 2S,3S-3-Hydroxyproline 11.Key steps of the reaction sequence were the stereoselective epoxidation of 1 to 2 and the regioselective ring opening of 2 to 3.BH3*S(CH3)2 reduction of the amide group of 3 and 4 resulted in a concomitant transformation of the acetal moiety into the N-benzyl protecting group.The air sensitive 5 and 6, were transformed to the stable N-Boc prolinol derivatives 7 and 8.Deprotection of 8 provided 9, while oxidation of 8 gave the protected proline derivative 10.Deprotection of 10 furnished enantiopure 2S,3S-3-Hydroxyproline 11.