HCID 15222237, 화합물 → 1-[(1R,2R,4S,5R)-2-tetrahydropyranyloxy-4-t-butylsilyloxy-5-(2(RS)-hydroxy-3,3-difluoro-7-t-butyldimethylsilyloxy-4-heptynyl}-cyclopentyl]-3,3-ethylenedioxy-octane

HRID 21922

반응식

HRID 21922 반응식
[CH2:1]1[CH2:33][O:32][C:3]([CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])([CH2:4][CH2:5][C@H:6]2[C@H:10]([O:11][CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][O:13]3)[CH2:9][C@H:8]([O:18][SiH2:19][C:20]([CH3:23])([CH3:22])[CH3:21])[C@H:7]2[CH2:24][CH:25]=[O:26])[O:2]1.Br[C:35]([F:49])([F:48])[C:36]#[C:37][CH2:38][CH2:39][O:40][Si:41]([C:44]([CH3:47])([CH3:46])[CH3:45])([CH3:43])[CH3:42]>C1COCC1.[Zn].[Hg]Cl>[O:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH:12]1[O:11][C@@H:10]1[CH2:9][C@H:8]([O:18][SiH2:19][C:20]([CH3:21])([CH3:23])[CH3:22])[C@H:7]([CH2:24][CH:25]([OH:26])[C:35]([F:49])([F:48])[C:36]#[C:37][CH2:38][CH2:39][O:40][Si:41]([C:44]([CH3:45])([CH3:46])[CH3:47])([CH3:43])[CH3:42])[C@H:6]1[CH2:5][CH2:4][C:3]1([O:2][CH2:1][CH2:33][O:32]1)[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

참가 물질

6

반응물 2

HCID 15222237HCID 15222237, 화합물HCID 1232181622-[(1S,2R,3R,5S)-2-(3,3-ethylenedioxyoctyl)-3-(tetrahydropyranyloxy)-5-(t-butylsiloxy)cyclopentyl]acetaldehyde

생성물 1

HCID 1234960171-[(1R,2R,4S,5R)-2-tetrahydropyranyloxy-4-t-butylsilyloxy-5-(2(RS)-hydroxy-3,3-difluoro-7-t-butyldimethylsilyloxy-4-heptynyl}-cyclopentyl]-3,3-ethylenedioxy-octane

시약·촉매·용매 3

HCID 23994Zinc촉매HCID 24182Mercurous Chloride촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of 2-[(1S,2R,3R,5S)-2-(3,3-ethylenedioxyoctyl)-3-(tetrahydropyranyloxy)-5-(t-butylsiloxy)cyclopentyl]acetaldehyde (64) (1.00 g) in THF (25 ml) was added activated zinc powder (2.54 g), and while cooling on ice, the solution of 1-bromo-1,1-difluoro-5-(t-butyl-dimethylsilyloxy)-2-pentyne (i) (0.92 g) in THF (5 ml) was added dropwise to the resultant mixture. To the resultant solution was added mercury chloride (0.11 g) and the resultant mixture was stirred under ultrasonic irradiation. The reaction mixture was treated in the conventional manner and the obtained crude product was subjected to silica gel column chromatography to give the title compound (65).

후처리

  1. temperaturewhile cooling on ice
  2. additionThe reaction mixture was treated in the conventional manner
  3. customthe obtained crude product

출처 및 근거

ORD 기록
ord-03ea2f543c9c4c50826dfdd180319a84
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05426115

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