154631-82-0

Basic information

• Product Name: (2R,5R,6R,7R)-6,7-epoxy-2-phenyl-3-oxa-1-aza-bicyclo<3.3.0>octane-8-one
• Synonyms: (2R,5R,6R,7R)-6,7-epoxy-2-phenyl-3-oxa-1-aza-bicyclo<3.3.0>octane-8-one
• CAS NO: 154631-82-0
• Molecular Weight: 217.224
• Mol File: 154631-82-0.mol

Chemical Properties

• CAS DataBase Reference: (2R,5R,6R,7R)-6,7-epoxy-2-phenyl-3-oxa-1-aza-bicyclo<3.3.0>octane-8-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,5R,6R,7R)-6,7-epoxy-2-phenyl-3-oxa-1-aza-bicyclo<3.3.0>octane-8-one(154631-82-0)
• EPA Substance Registry System: (2R,5R,6R,7R)-6,7-epoxy-2-phenyl-3-oxa-1-aza-bicyclo<3.3.0>octane-8-one(154631-82-0)

Safety Data

• Hazardous Substances Data: 154631-82-0(Hazardous Substances Data)

Upstream product

• 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

• 156045-80-6 (2R,5R,6S)-6-tert-butyldimethylsiloxy-3-oxa-2-phenyl-1-azabicyclo<3.3.0>octane-8-one 
• 156045-81-7 (2R,3S)-1-benzyl-3-tert-butyldimethylsilyloxy-2-hydroxymethylpyrrolidine 
• 121686-87-1 (2R,3S)-N-benzyl-3-hydroxy-2-hydroxymethylpyrrolidine 
• 98900-30-2 (2R,3S)-2-hydroxymethyl-3-hydroxypyrrolidinium hydrochloride 
• 4298-08-2 trans-3-hydroxy-L-proline 
• 100937-52-8 1,4-dideoxy-1,4-imino-D-arabitol 
• 202473-18-5 (2S,3S,4R)-3-hydroxy-4-aminoproline 
• 194737-67-2 tert-butyl (2R,3S,4R)-4-tert-butoxycarboxamido-2-tert-butyldiphenylsilyloxymethyl-3-mesyloxy-pyrrolidine-1-carboxylate 
• 194737-66-1 tert-butyl (2R,3S,4R)-4-tert-butoxycarboxamido-2-tert-butyldiphenylsilyloxymethyl-3-hydroxy-pyrrolidine-1-carboxylate 
• 194737-65-0 tert-butyl (2R,3R,4R)-4-azido-2-tert-butyldiphenylsilyloxymethyl-3-hydroxy-pyrrolidine-1-carboxylate 
• 194737-63-8 tert-butyl (2R,3R,4S)-2-tert-butyldiphenylsilyloxymethyl-3,4-epoxypyrrolidine-1-carboxylate 
• 251987-24-3 (2R,3R,4R)-N-benzyloxy-4-(N-tert-butoxycarbonyl)amino-2,3-epoxy-5-[(1-ethoxy)ethoxy]pentanamide 
• 251987-20-9 (2R,3R,4R)-N-benzyl-4-(N-tert-butoxycarbonyl)amino-2,3-epoxy-5-[(1-ethoxy)ethoxy]pentanamide 
• 751456-32-3 (3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-pyrrolidin-2-one 

Relevant articles and documents

Stereoselective oxygenation of bicyclic lactams

Stereoselective syntheses of the epoxy and diol derivatives of a bicyclic lactam derived from pyroglutamic acid are reported, and their reactivity is discussed.

Synthesis of trans-epoxy-L-proline and cis-aziridino-L-proline from S-pyroglutamic acid. Regio- and diastereoselective ring opening of its derivatives

The pyroglutamic acid derivative 4 was converted through several steps into 2S,3R,4S-epoxyproline 8. Key steps of the reaction sequence were the stereoselective epoxidation of 4 to 5 and the chemoselective reduction of the amide group of 5 with concomitan

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.

A concise diastereoselective synthesis of the natural (2R, 3S)2-hydroxymethyl-3-hydroxy pyrrolidine

(2R, 3S)-2-hydroxymethyl-3-hydroxy pyrrolidine 4, a constituent of CAstanospermum ausfrale, 1 was synthesized from (S)-pyroglutamic acid through diastereoselective epoxidation of α, β-unsaturated pyrrolidone 8.