3,4-dihydro-2H-pyran → trans-6-Hydroxymethyl-2-methoxytetrahydropyran

HRID 466269

반응식

HRID 466269 반응식
O1C=CCCC1.[CH3:7][O:8][CH:9]1[CH:14]=[CH:13][CH2:12][CH:11]([C:15](OC)=[O:16])[O:10]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CO.Cl.C(OCC)C.[Pt](=O)=O>[OH:16][CH2:15][C@@H:11]1[O:10][C@@H:9]([O:8][CH3:7])[CH2:14][CH2:13][CH2:12]1

참가 물질

8

반응물 3

HCID 80803,4-dihydro-2H-pyranHCID 5572662H-Pyran-2-carboxylic acid, 3,6-dihydro-6-methoxy-, methyl esterHCID 21226445Aluminium lithium hydride

생성물 1

HCID 13108355trans-6-Hydroxymethyl-2-methoxytetrahydropyran

시약·촉매·용매 4

HCID 313Hydrochloric Acid촉매HCID 345198Adams' catalyst촉매HCID 887Methanol용매2회HCID 3283Diethyl Ether용매

실험 절차

The absolute configuration for the product was determined by first isomerizing the dihydropyran derivative product in methanol by use of hydrochloric acid as a catalyst so that the product had a trans-isomer content of 95%, subsequently converting the ester into an alcohol in diethyl ether by use of lithium aluminum hydride, and then hydrogenating the double bonds by using platinum dioxide in methanol to give trans-6-hydroxymethyl-2-methoxytetrahydropyran, followed by optical rotation measurement. As a result, the optical rotation [α]20 of the above compound was found to be -119.9° (c=1.07, solvent: benzene). This found value was compared with the optical rotation [α]20 of +129.7° (c=4.3, solvent: benzene) for (2S,6S)-6-hydroxymethyl-2-methoxy-3,4,5,6-tetrahydropyran as described in J. Jurczak et al., J. Chem. Soc., Chem. Commun., pp. 540-542 (1983). Based on the comparison, the trans-isomer and cis-isomer were judged to be a (2R,6R)-isomer and a (2S,6R)-isomer, respectively.

출처 및 근거

ORD 기록
ord-015bccbdc4b14c03a46a0c18658a7ee9
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05155240

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