反応 #50199

ord-e332d81194304245b3b4652b8b3df799

反応方程式

CCCCCC1(CC[C@@H]2[C@H](CC(=O)OC)[C@@H](O)C[C@H]2OC2CCCCO2)OCCO1
methyl 2-[(1S,2R,3R,5S)-2-(3,3-ethylenedioxyoctyl)-3-(tetrahydropyranyloxy)-5-hydroxycyclopentyl]acetate
CC(C)(C)[Si](C)(C)Cl
t-butyldimethylsilyl chloride
c1c[nH]cn1
imidazol
→
CCCCCC1(CC[C@@H]2[C@H](CC(=O)OC)[C@@H](O[SiH2]C(C)(C)C)C[C@H]2OC2CCCCO2)OCCO1
title compound ( 62 )
CCCCCC1(CC[C@@H]2[C@H](CC(=O)OC)[C@@H](O[SiH2]C(C)(C)C)C[C@H]2OC2CCCCO2)OCCO1
methyl 2-[(1S,2R,3R,5S)-2-(3,3-ethylenedioxyoctyl)-3-(tetrahydropyranyloxy)-5-(t-butylsilyloxy)cyclopentyl]acetate

反応物

—
resultant mixture
CCCCCC1(CC[C@@H]2[C@H](CC(=O)OC)[C@@H](O)C[C@H]2OC2CCCCO2)OCCO1
methyl 2-[(1S,2R,3R,5S)-2-(3,3-ethylenedioxyoctyl)-3-(tetrahydropyranyloxy)-5-hydroxycyclopentyl]acetate
CC(C)(C)[Si](C)(C)Cl
t-butyldimethylsilyl chloride
c1c[nH]cn1
imidazol

試薬

なし

溶媒

CN(C)C=O
DMF

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    その他The crude product obtained
  2. 2
    workup.ADDITIONby treating in the conventional manner

実験手順

To a solution of methyl 2-[(1S,2R,3R,5S)-2-(3,3-ethylenedioxyoctyl)-3-(tetrahydropyranyloxy)-5-hydroxycyclopentyl]acetate (61) in DMF (80 ml) were added t-butyldimethylsilyl chloride (2.11 g) and imidazol (0.95 g), and the resultant mixture was stirred. The crude product obtained by treating in the conventional manner was subjected to silica gel column chromatography to give the title compound (62).

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US05426115uspto-grants-1995_06