(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

반응식

HRID 6787 반응식
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

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 9942167Palladium hydroxide촉매HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b818d872f7424cc0b8956ae887e47d40
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084125B2

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