تفاعل #50199

ord-e332d81194304245b3b4652b8b3df799

معادلة التفاعل

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

المتفاعلات

—
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

الكواشف

لا شيء

المذيبات

CN(C)C=O
DMF

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىThe crude product obtained
  2. 2
    workup.ADDITIONby treating in the conventional manner

الإجراء التجريبي

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).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US05426115uspto-grants-1995_06