HCID 15222237、化合物 → 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 2226241ノート

反応式

HRID 2226241 の反応式
[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]

参加物

6

反応物 2

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

生成物 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

試薬・触媒・溶媒 3

HCID 23994Zinc触媒HCID 24182Mercurous Chloride触媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-5ad531bf66084a17bdbcacc10f7a0af5
出典データセット
uspto-grants-1994_09
特許番号
US05346921

反応ノート

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