(1S,4R,5R,7R,8R)-4,8-Dibenzyloxy-7-(thymin-1-yl)-2,6-Dioxabicyclo [3.2.1]Octane → (1S,4R,5R,7R,8R)-4,8-Dihydroxy-7-(thymin-1-yl)-2,6-dioxabicyclo[3.2.1]octane

HRID 6787

反応式

HRID 6787 の反応式
C([O:8][C@H:9]1[C@@H:15]2[C@@H:16]([O:17]CC3C=CC=CC=3)[C@@H:12]([C@H:13]([N:25]3[CH:33]=[C:31]([CH3:32])[C:29](=[O:30])[NH:28][C:26]3=[O:27])[O:14]2)[O:11][CH2:10]1)C1C=CC=CC=1>C(O)C.[OH-].[OH-].[Pd+2]>[OH:8][C@H:9]1[C@@H:15]2[C@@H:16]([OH:17])[C@@H:12]([C@H:13]([N:25]3[CH:33]=[C:31]([CH3:32])[C:29](=[O:30])[NH:28][C:26]3=[O:27])[O:14]2)[O:11][CH2:10]1

参加物

4

反応物 1

HCID 57198644(1S,4R,5R,7R,8R)-4,8-Dibenzyloxy-7-(thymin-1-yl)-2,6-Dioxabicyclo [3.2.1]Octane

生成物 1

HCID 67527748(1S,4R,5R,7R,8R)-4,8-Dihydroxy-7-(thymin-1-yl)-2,6-dioxabicyclo[3.2.1]octane

試薬・触媒・溶媒 2

HCID 9942167Palladium hydroxide触媒HCID 702Ethanol溶媒

実験手順

Nucleoside 18 (0.27 g, 0.60 mmol) was dissolved in absolute ethanol (20 cm3) and 20% palladium hydroxide on carbon (0.25 g) was added. The mixture was degassed and placed under an atmosphere of hydrogen. After stirring for 26 h the catalyst was filtered off (silica gel, washed with methanol, 400 cm3) and the filtrate was concentrated to dryness under reduced pressure. The residue was subjected to column chromatography on silica gel using dichloromethane/methanol (94:6, v/v) as eluent to give nucleoside 19 as white solid material (0.16 g, 98%) after evaporation of the solvents under reduced pressure.

後処理

  1. customThe mixture was degassed
  2. filtrationwas filtered off
  3. wash(silica gel, washed with methanol, 400 cm3)
  4. concentrationthe filtrate was concentrated to dryness under reduced pressure

出典と根拠

ORDレコード
ord-b818d872f7424cc0b8956ae887e47d40
出典データセット
uspto-grants-2006_08
特許番号
US07084125B2

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