132639-34-0

Basic information

• Product Name: tert-Butyl (E,4S)-2,2-dimethyl-4-(2'-phenylvinyl)-3-oxazolidine-3-carboxylate
• Synonyms: tert-Butyl (E,4S)-2,2-dimethyl-4-(2'-phenylvinyl)-3-oxazolidine-3-carboxylate
• CAS NO: 132639-34-0
• Molecular Weight: 303.401
• Mol File: 132639-34-0.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: tert-Butyl (E,4S)-2,2-dimethyl-4-(2'-phenylvinyl)-3-oxazolidine-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-Butyl (E,4S)-2,2-dimethyl-4-(2'-phenylvinyl)-3-oxazolidine-3-carboxylate(132639-34-0)
• EPA Substance Registry System: tert-Butyl (E,4S)-2,2-dimethyl-4-(2'-phenylvinyl)-3-oxazolidine-3-carboxylate(132639-34-0)

Safety Data

• Hazardous Substances Data: 132639-34-0(Hazardous Substances Data)

Upstream product

• 1080-32-6 O,O-diethyl benzylphosphonate 
• 95715-87-0 (R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine 
• 1449-46-3 benzyltriphenylphosphonium bromide 

Downstream Products

• 505085-76-7 (2R,3E)-2-amino-4-phenylbut-3-en-1-ol 
• 132639-33-9 (2S,1'S,2'S,E)-α-(2-Phenylcyclopropyl)glycine hydrochloride 
• 132639-32-8 [2-Hydroxy-1-((1S,2S)-2-phenyl-cyclopropyl)-ethyl]-carbamic acid tert-butyl ester 
• 132697-90-6 (E)-α-(2-phenylcyclopropyl)glycine hydrochloride 
• 140225-07-6 tert-butyl (E)-<2-hydroxy-1-(2'-phenylcyclopropyl)>-N-ethylcarbamate 
• 132639-36-2 tert-butyl (E)-4-(2'-phenylcyclopropyl)-2,2-dimethyl-3-oxazolidinecarboxylate 
• 652539-07-6 (4R,1'S)-3-(1-dodecylbut-3-enyl)-4-styryloxazolidin-2-one 
• 652539-06-5 (2R,1'S)-2-(1-dodecylbut-3-enylamino)-4-phenylbut-3-en-1-ol 
• 505085-92-7 (4R,1'R)-3-(1-cyclohexylbut-3-enyl)-4-styryloxazolidin-2-one 
• 505085-90-5 (4R,1'S)-3-(1-phenylethylbut-3-enyl)-4-styryloxazolidin-2-one 
• 505085-91-6 (4R,1'S)-3-(1-hexylbut-3-enyl)-4-styryloxazolidin-2-one 
• 505085-84-7 (2R,1'R)-2-(1-cyclohexylbut-3-enylamino)-4-phenylbut-3-en-1-ol 
• 505085-82-5 (2R,1'S)-4-phenyl-2-(1-phenylethylbut-3-enylamino)but-3-en-1-ol 

Relevant articles and documents

First Total Synthesis of 1-O-β-D-Glucopyranosyl-5-deoxyadenophorine and Its Aglycon Congener: Determination of the Absolute Configuration

The first total synthesis of the potent glycosidase inhibitors 1-O-β-D-glucopyranosyl-5-deoxyadenophorine and its aglycon congener is described in respectively 13 steps (9% overall yield) and 9 steps (29% overall yield) from (R)-Garner aldehyde. The synthesis takes advantage of several key reactions including a diastereoselective allylation of a chiral imine, a stereoselective epoxidation, and a glycoside coupling. In addition this study established unambiguously the absolute configuration of the natural products.

Efficient access to chiral trans-2,6-dialkyl-1,2,5,6-tetrahydropyridines via allylation of chiral imines and ring-closing metathesis

Enantiomerically pure trans-2,6-dialkyl-1,2,5,6-tetrahydropyridines are synthesized in five steps from Garner's aldehyde in 37-44% overall yield. This strategy is based on the allylation of chiral iminoalcohols formed in situ followed by a ring-closing metathesis.

Synthesis of asymmetric (E)-α-(2-phenylcyclopropyl)glycines

An asymmetric synthesis of (E)-α-(2-phenylcyclopropyl)glycines is reported. The key step is the dibromocyclopropanation of tert-Butyl (E,4R) or (E,4S)-2,2-dimethyl-4-(2'-phenylvinyl)-3-oxazolidinecarboxylates, easily prepared from L or D-serine, respectiv