100101-26-6

Basic information

• Product Name: (S)-1-[(R)-piperidin-2-yl]propan-1-ol [(-)-α-conhydrine]
• CAS NO: 100101-26-6
• Molecular Weight: 143.229
• Mol File: 100101-26-6.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: (S)-1-[(R)-piperidin-2-yl]propan-1-ol [(-)-α-conhydrine](CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1-[(R)-piperidin-2-yl]propan-1-ol [(-)-α-conhydrine](100101-26-6)
• EPA Substance Registry System: (S)-1-[(R)-piperidin-2-yl]propan-1-ol [(-)-α-conhydrine](100101-26-6)

Safety Data

• Hazardous Substances Data: 100101-26-6(Hazardous Substances Data)

Upstream product

• 1403599-33-6 benzyl (3R,4S)-4-(benzyloxy)-1-phenylhex-1-en-3-ylcarbamate 
• 1403599-36-9 (R)-6-[(S)-1-(benzyloxy)propyl]-1,2,3,6-tetrahydropyridine 
• 1403599-35-8 (3R,4S)-4-(benzyloxy)-N-(but-3-enyl)-1-phenylhex-1-en-3-amine 
• 1403599-34-7 (3R,4S,Z)-4-(benzyloxy)-1-phenylhex-1-en-3-amine 
• 1210445-07-0 (R)-6-((S)-1-(tert-butyldimethylsilyloxy)propyl)piperidin-2-one 
• 38726-77-1 conhydrinone hydrochloride 
• 530739-50-5 [5-hydroxy-1-(1-hydroxypropyl)-pent-2-enyl]-carbamic acid tert-butyl ester 
• 530739-51-6 [5-hydroxy-1-(1-hydroxypropyl)-pentyl]-carbamic acid tert-butyl ester 
• 530739-49-2 methyl (2S,3S)-2-tert-butoxycarbonylamino-3-hydroxypentanoate 
• 869660-13-9 ((1S,2S)-1-Formyl-2-hydroxy-butyl)-carbamic acid tert-butyl ester 
• 530739-47-0 (2R,3S)-5-ethyl-2,2-dioxo-[1,3,2]dioxathiolane-4-carboxylic acid methyl ester 
• 530739-48-1 methyl (2S,3S)-2-azido-3-hydroxypentanoate 
• 262844-06-4 (2R,3S)-2,3-dihydroxypentanoic acid methyl ester 
• 15790-87-1 Methyl (E)-2-pentenoate 

Relevant articles and documents

Short and efficient asymmetric synthesis of (-)-α-conhydrine

(Chemical Equation Presented) The short and efficient synthesis of (-)-α-conhydrine was accomplished with 41% overall yield in seven steps and high diastereo- and enantioselectivity. The anti-stereochemistry of the two stereogenic centers has been confirmed by the single-crystal X-ray analysis of an intermediate.

Stereoselective synthesis of (-)-α-conhydrine and its pyrrolidine analogue

The stereoselective synthesis of (-)-α-conhydrine and its pyrrolidine analogue was achieved from readily available D-erythronolactone. The key step of this synthesis includes a highly regioselective and diastereoselective addition of chlorosulfonyl isocyanate to 1,2-anti-dibenzyl ether to afford the 1,2-anti-amino alcohol. The total synthesis of (-)-α-conhydrine and its pyrrolidine analogue starting from readily available D-erythronolactone was achieved via the regioselective and diastereoselective allylic amination of anti-1,2-dibenzyl ether by using chlorosulfonyl isocyanate.

Highly enantioselective synthesis of chiral cyclic amino alcohols and conhydrine by ruthenium-catalyzed asymmetric hydrogenation

A highly efficient enantio- and diastereoselective synthesis of chiral cis-β-N-alkyl/arylamino cyclic alcohols has been realized by asymmetric hydrogenation of racemic α-amino cyclic ketones via DKR catalyzed by [RuCl2((S)-Xyl-SDP)((R,R)-DPEN)]. The enantioselectivities of the reaction were up to 99.9% ee with 99:1 cis-selectivities. A practical catalytic asymmetric synthesis of all four isomers of conhydrine was also developed.