Reacción #430073

ord-aaa1e7c9273e495db8372e9621a9530e

Ecuación de reacción

CCCCCCCCCBr
1-bromononane
Nc1ncnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
adenosine
[H-].[Na+]
sodium hydride
→
CCCCCCCCCO[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1n1cnc2c(N)ncnc21
title compound
CCCCCCCCCO[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1n1cnc2c(N)ncnc21
2'-O-Nonyladenosine

Reactantes

CCCCCCCCCBr
1-bromononane
Nc1ncnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
adenosine
[H-].[Na+]
sodium hydride

Reactivos

Ninguno

Disolventes

CN(C)C=O
dimethyl formamide

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    workup.ADDITIONIce was added
  2. 2
    Otrothe solution evaporated in vacuo
  3. 3
    workup.ADDITIONWater and ethyl acetate were added
  4. 4
    OtroThe organic phase was separated
  5. 5
    Otrodried
  6. 6
    Otroevaporated in vacuo
  7. 7
    Otroto give a white solid, which
  8. 8
    Otrowas recrystallized from ethanol

Procedimiento

To a solution of 10 g of adenosine in 400 ml of dimethyl formamide was added 2.25 g of 60% sodium hydride (oil). After one hour, 8.5 ml of 1-bromononane was added. The reaction was stirred for 16 hours. Ice was added and the solution evaporated in vacuo. Water and ethyl acetate were added. The organic phase was separated, dried, and evaporated in vacuo to give a white solid, which was recrystallized from ethanol to yield 4.8 g of the title compound, m.p. 143°-144° C. analysis for: C19H31N5O4Calculated: C, 57.99; H, 7.94; N, 1779. Found: C, 58.13; H, 7.93; N, 17.83.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05859221uspto-grants-1999_01