Pyridine, hydrofluoride (1:1) → methyl(11R,12S,13E)-9-butyryloxy-11,15-dihydroxy-16,16,20-trimethyl-7-thiaprosta-8,13-dienoate

HRID 3036

반응식

N1C=CC=CC=1.F.[C:8]([O:13][C:14]1[CH2:28][C@@H:27]([O:29][Si](C(C)(C)C)(C)C)[C@H:26](/[CH:37]=[CH:38]/[CH:39]([OH:48])[C:40]([CH3:47])([CH3:46])[CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[C:15]=1[S:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])(=[O:12])[CH2:9][CH2:10][CH3:11]>>[C:8]([O:13][C:14]1[CH2:28][C@@H:27]([OH:29])[C@H:26](/[CH:37]=[CH:38]/[CH:39]([OH:48])[C:40]([CH3:46])([CH3:47])[CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[C:15]=1[S:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])(=[O:12])[CH2:9][CH2:10][CH3:11]

참가 물질

반응물 2

HCID 64774Pyridine, hydrofluoride (1:1)

HCID 22883818methyl(11R,12S,13E)-9-butyryloxy-11-tert-butyldimethylsiloxy-15-hydroxy-16,16,20-trimethyl-7-thiaprosta-8,13-dienoate

생성물 1

HCID 22883815methyl(11R,12S,13E)-9-butyryloxy-11,15-dihydroxy-16,16,20-trimethyl-7-thiaprosta-8,13-dienoate

실험 절차

Using as the materials a hydrogen fluoride-pyridine solution (0.25 ml) and methyl(11R,12S,13E)-9-butyryloxy-11-tert-butyldimethylsiloxy-15-hydroxy-16,16,20-trimethyl-7-thiaprosta-8,13-dienoate (100 mg), the same procedure as in Example 2 was performed to separately obtain two stereoisomers of methyl(11R,12S,13E)-9-butyryloxy-11,15-dihydroxy-16,16,20-trimethyl-7-thiaprosta-8,13-dienoate different at the 15-position. (Low polarity compound: 26 mg, 33%; high polarity compound: 28 mg, 35%)

출처 및 근거

ORD 기록: ord-e387f53034b342bebeac204bcb29c54a
출처 데이터셋: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US05731452

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