The origin of a common compound about 1824-94-8

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Electric Literature of C7H14O6. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: (2R,3R,4S,5R,6R)-2-(Hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol, is researched, Molecular C7H14O6, CAS is 1824-94-8, about Synthesis of chiral crown ethers derived from D-galactose and their application in enantioselective reactions. Author is Rapi, Zsolt; Nemcsok, Tamas; Bagi, Peter; Keglevich, Gyorgy; Bako, Peter.

A few new α- and β-D-galactopyranoside-based chiral lariat ethers of mono-aza-15-crown-5 type were synthesized. These macrocycles proved to be efficient catalysts in a few asym. reactions under mild phase transfer conditions. The catalytic effect of the lariat ethers with methoxy, ethoxy, isopropoxy and aryloxy substituents on the C-1 of the sugar unit in both α and β positions was compared. In the presence of β-D-galactopyranoside-based crown ethers, the asym. Darzens condensation of α-chloroacetophenone and benzaldehyde, the epoxidation of trans-chalcone, the cyclopropanation (MIRC reaction) of benzylidenemalononitrile and 2-benzylidene-1,3-indandione with di-Et bromomalonate were performed with enantioselectivities of 61%, 64%, 86% and 96%, resp. In all reactions, the β-anomers were more efficient in terms of enantioselectivity than the α forms.

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Reference:
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate