Methanol → HCID 20448815、化合物

反応式

[Si:1]([O:8][CH:9]1[CH2:13][C:12](=O)[CH:11]2[O:15][CH:10]12)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].O[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][SH:22].C(N(CC)CC)C.[CH3:30][OH:31]>>[Si:1]([O:8][CH:9]1[CH2:10][C:11](=[O:15])[C:12]([S:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:30][OH:31])=[CH:13]1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

参加物

反応物 4

HCID 887Methanol

HCID 8471Triethylamine

HCID 5342595-Mercapto-1-pentanol

HCID 133625094(RS)-t-butyldimethylsilyloxy-2,3-epoxycyclopentanone

生成物 1

HCID 20448815HCID 20448815、化合物収率 31%

実験手順

1.26 g (5.94 mmoles) of 4(RS)-t-butyldimethylsilyloxy-2,3-epoxy cyclopentanone and 804 mg (6.0 mmoles) of 5-hydroxy-1-pentanethiol were dissolved in 10 ml of methanol, and 606 mg (6 mmoles) of triethylamine was added. After the reaction was carried out for 10 minutes, the solvent was evaporated to give 2.1 g of a crude product. The crude product was subjected to dry column chromatography and developed with hexane/ethyl acetate (7/3) to give 710 mg (2.16 mmoles; yield 31%) of 4-t-butyldimethylsilyloxy-2-(6-hydroxyhexylthio)-2-cyclopentenone.