160169-49-3

Basic information

• Product Name: [1R-(1a,2,8aa)]-Hexahydro-1,2-dihydroxy-3(2H)-indolizinone
• Synonyms: (1R,2S,8aR)-Hexahydro-1,2-dihydroxy-3(2H)-indolizinone;[1R-(1a,2,8aa)]-Hexahydro-1,2-dihydroxy-3(2H)-indolizinone;3-Oxo-(-)-lentiginosine;(1R,2S,8aR)-
• CAS NO: 160169-49-3
• Molecular Formula: C8H13NO3
• Molecular Weight: 171.19
• Product Categories: Chiral Reagents;Heterocycles
• Mol File: 160169-49-3.mol

Chemical Properties

• Boiling Point: 357.7±42.0 °C(Predicted)
• Appearance: /
• Density: 1.37±0.1 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 13.13±0.40(Predicted)
• CAS DataBase Reference: [1R-(1a,2,8aa)]-Hexahydro-1,2-dihydroxy-3(2H)-indolizinone(CAS DataBase Reference)
• NIST Chemistry Reference: [1R-(1a,2,8aa)]-Hexahydro-1,2-dihydroxy-3(2H)-indolizinone(160169-49-3)
• EPA Substance Registry System: [1R-(1a,2,8aa)]-Hexahydro-1,2-dihydroxy-3(2H)-indolizinone(160169-49-3)

Safety Data

• Hazardous Substances Data: 160169-49-3(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Upstream product

• 160096-51-5 (R)-2-((1R,2S)-2-Ethoxycarbonyl-1,2-dihydroxy-ethyl)-piperidine-1-carboxylic acid benzyl ester 
• 839711-89-6 (2S,3R)-isopropyl 2,3-dihydroxy-3-(N-oxypyridin-2-yl)propanoate 
• 839711-94-3 (E)-isopropyl 3-(pyridin-2-yl)acrylate 
• 839711-81-8 (E)-isopropyl 3-(N-oxypyridin-2-yl)acrylate 
• 28697-07-6 (R)-1-((benzyloxy)carbonyl)piperidine-2-carboxylic acid 
• 154499-13-5 benzyl (R)-2-(hydroxymethyl)piperidine-1-carboxylate 
• 1068012-41-8 (R)-N-(benzyloxycarbonyl)-2-formylpiperidine 
• 160169-47-1 (R)-2-((E)-2-Ethoxycarbonyl-vinyl)-piperidine-1-carboxylic acid benzyl ester 
• 1723-00-8 (R)-(+)-pipecolic acid 
• 134526-69-5 tert-butoxycarbonyl-D-piperidine-2-carboxaldehyde 
• 1268624-36-7 (R,E)-tert-butyl 2-(3-ethoxy-3-oxoprop-1-enyl)piperidine-1-carboxylate 
• 1013212-42-4 tert-butyl 1-(R)-2-((S)-1,2-dihydroxylethyl)piperidine-1-carboxylate 
• 1268624-35-6 (R)-tert-butyl 2-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)piperidine-1-carboxylate 
• 1268624-34-5 (R)-tert-butyl 6-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-5,6-dihydropyridine-1(2H)-carboxylate 

Downstream Products

• 125279-72-3 (1R,2R,8aR)-lentiginosine 

Relevant articles and documents

An expedient total synthesis of optically active piperidine and indolizidine alkaloids (-)-β-conhydrine and (-)-lentiginosine

Attempts directed toward the stereocontroled total synthesis of piperidine and indolizidine alkaloids resulted in the synthesis of (-)-β-conhydrine 1 and (-)-lentiginosine 3. The synthesis of 1 and 3 were developed from protected d-mannitol as the chiral

Stereoselective synthesis of swainsonines from pyridines

An efficient synthesis of (-)-swainsonine and (-)-2,8a-di-epi-swainsonine was developed starting from readily available 2-pyridinecarbaldehyde and 3-hydroxypyridine. In particular, it was demonstrated that the mixture of simple indolizidines, i.e. lentigi

Stereoselective synthesis of (+)-and (-)-lentiginosine

Simple routes to (1R,2R,8aR)- and (1S,2S,8aS)-lentiginosine have been described, based on Sharpless asymmetric dihydroxylation, starting from (R)- and (S)-pipecolinic acids.