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125279-72-3

125279-72-3 | 1,2-Indolizinediol, octahydro-, (1R,2R,8aR)-

CAS No: 125279-72-3 Catalog No: AG000NFM MDL No:

Product Description

Catalog Number:
AG000NFM
Chemical Name:
1,2-Indolizinediol, octahydro-, (1R,2R,8aR)-
CAS Number:
125279-72-3
Molecular Formula:
C8H15NO2
Molecular Weight:
157.2102
IUPAC Name:
(1R,2R,8aR)-1,2,3,5,6,7,8,8a-octahydroindolizine-1,2-diol
InChI:
InChI=1S/C8H15NO2/c10-7-5-9-4-2-1-3-6(9)8(7)11/h6-8,10-11H,1-5H2/t6-,7-,8-/m1/s1
InChI Key:
SQECYPINZNWUTE-BWZBUEFSSA-N
SMILES:
O[C@@H]1CN2[C@@H]([C@H]1O)CCCC2

Properties

Complexity:
151  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
3  
Defined Bond Stereocenter Count:
0
Exact Mass:
157.11g/mol
Formal Charge:
0
Heavy Atom Count:
11  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0
Molecular Weight:
157.213g/mol
Monoisotopic Mass:
157.11g/mol
Rotatable Bond Count:
0
Topological Polar Surface Area:
43.7A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-0.3  

Literature

Title Journal
Synthesis of 1,2-dihydroxyindolizidines from 1-(2-pyridyl)-2-propen-1-ol. The Journal of organic chemistry 20111118
The novel proapoptotic activity of nonnatural enantiomer of Lentiginosine. Glycobiology 20100501
Sterically biased 3,3-sigmatropic rearrangement of chiral allylic azides: application to the total syntheses of alkaloids. The Journal of organic chemistry 20080815
Binding of sulfonium-ion analogues of di-epi-swainsonine and 8-epi-lentiginosine to Drosophila Golgi alpha-mannosidase II: the role of water in inhibitor binding. Proteins 20080515
Efficient synthesis of (+)-1,8,8a-tri-epi-swainsonine, (+)-1,2-di-epi-lentiginosine, (+)-9a-epi-homocastanospermine and (-)-9-deoxy-9a-epi-homocastanospermine from a D-glucose-derived aziridine carboxylate, and study of their glycosidase inhibitory activities. Organic & biomolecular chemistry 20080221
A concise synthesis of lentiginosine derivatives using a pyridinium formation via the Mitsunobu reaction. The Journal of organic chemistry 20080201
New access to indolizidine and pyrrolizidine alkaloids from an enantiopure proline: total syntheses of (-)-lentiginosine and (1R,2R,7aR)-dihydroxypyrrolizidine. The Journal of organic chemistry 20070720
Regioselective and diastereoselective amination of polybenzyl ethers using chlorosulfonyl isocyanate: total syntheses of 1,4-dideoxy-1,4-imino-D-arabinitol and (-)-lentiginosine. Organic letters 20060831
Asymmetric syntheses of (-)-lentiginosine and an original pyrrolizidinic analogue thereof from a versatile epoxyamine intermediate. Organic & biomolecular chemistry 20050721
Stereoselective allyl amine synthesis through enantioselective addition of diethylzinc and [1,3]-chirality transfer: synthesis of lentiginosine and polyoxamic acid derivative. Chemistry (Weinheim an der Bergstrasse, Germany) 20050304
Concise asymmetric syntheses of (-)-lentiginosine and of its pyrrolizidinic analogue. Chemical communications (Cambridge, England) 20030307
Total synthesis of (-)- and (+)-lentiginosine. The Journal of organic chemistry 20020628
Synthesis of polyhydroxyindolizidines from 5,6-dihydro-2H-pyran-2-one. Carbohydrate research 20011207
Enantiocontrolled preparation of indolizidines: synthesis of (-)-2-epilentiginosine and (+)-lentiginosine. The Journal of organic chemistry 20010810

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