70614-56-1

Basic information

• Product Name: N-benzyloxycarbonyl-(2S,4R)-4-hydroxypipecolic acid
• CAS NO: 70614-56-1
• Molecular Weight: 279.293
• Mol File: 70614-56-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: N-benzyloxycarbonyl-(2S,4R)-4-hydroxypipecolic acid(CAS DataBase Reference)
• NIST Chemistry Reference: N-benzyloxycarbonyl-(2S,4R)-4-hydroxypipecolic acid(70614-56-1)
• EPA Substance Registry System: N-benzyloxycarbonyl-(2S,4R)-4-hydroxypipecolic acid(70614-56-1)

Safety Data

• Hazardous Substances Data: 70614-56-1(Hazardous Substances Data)

Upstream product

• 133192-45-7 2-methyl 1-(phenylmethyl) cis-4-hydroxy-1,2-piperidinedicarboxylate 
• 133192-44-6 methyl cis-4-hydroxy-2-piperidinecarboxylate 
• 133192-43-5 (1α,5α)-2-(phenylmethyl)-6-oxa-2-azabicyclo<3.2.1>octan-7-one 
• 59182-85-3 benzyloxycarbonyl-L-baikiain 
• 147489-31-4 N-benzyloxycarbonyl-4-oxo-(S)-pipecolic acid tert-butyl ester 

Downstream Products

• 102410-63-9 Pic(3-OBzl)-Thr(H-MePhe-4Kps-Phg-)-D-Abu-Pro-OH*2HCl 
• 102410-62-8 Pic(3-OBzl)-Thr(Boc-MePhe-4Kps-Phg-)-D-Abu-Pro-OBu^t 
• 102410-44-6 3-Benzyloxy-pyridine-2-carboxylic acid ((3S,6S,15S,16R,22S)-3-benzyl-12-ethyl-4,16-dimethyl-2,5,11,14,18,21,24-heptaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentaaza-tricyclo[20.4.0.0^6,10]hexacos-15-yl)-amide 
• 102410-61-7 Boc-MePhe-4Kps-OMe 
• 102429-30-1 Boc-MePhe-4Kps-OH 
• 1844-40-2 (2S,4R)-4-hydroxypiperidine-2-carboxylic acid 
• 133192-47-9 bis(phenylmethyl) cis-4-(diphenylphosphonooxy)-1,2-piperidinedicarboxylate 
• 133192-46-8 bis(phenylmethyl) cis-4-hydroxy-1,2-piperidinedicarboxylate 

Relevant articles and documents

Diastereoselective synthesis of (2S,5S)- and (2S,5R)-N-benzyloxycarbonyl-5-hydroxypipecolic acids from trans-4-hydroxy-l-proline

An efficient diastereoselective synthesis of cis- and trans-5-hydroxy-(2S)-N-benzyloxycarbonyl pipecolic acids, starting from trans-4-hydroxy-l-proline is described. The key synthetic strategies involve the regioisomeric ring expansion of keto ester 8 and diastereoselective reduction of ketone 11 in high selectivity and yield.

PREPARATION OF TRANS-5-HYDROXY-L-PIPECOLIC ACID AND CIS-4-HYDROXY-L-PIPECOLIC ACID FROM L-BAIKIAIN (1,2,5,6-L-TETRAHYDROPYRIDINE-2-CARBOXYLIC ACID).

Z-trans-5-OH-L-pipecolic acid together with Z-cis-4-OH-L-pipecolic acid is obtained in a 7:3 ratio by reduction of the oxymercuration product of Z-L-baikiain (Z-1,2,5,6-L-tetrahydropyridine-2-carboxylic acid).The opposite composition ratio is obtained using mercuric trifluoroacetate, thus giving access to the preparation of either of the two isomers.