반응 #1693458

ord-78494f9bad5446a0a2381877d651a364

반응 방정식

C[C@]12CC[C@@H]3c4c(O)cc(O)cc4CC[C@@H]3[C@@H]1C[C@@H](O)[C@@H]2O
8α-estra-1,3,5(10)-triene-1,3,16α,17β-tetrol
CS(=O)(=O)Cl
methanesulfonic acid chloride
→
C[C@]12CC[C@@H]3c4c(cc(OS(C)(=O)=O)cc4OS(C)(=O)=O)CC[C@@H]3[C@@H]1C[C@@H](OS(C)(=O)=O)[C@@H]2OS(C)(=O)=O
rac.-1,3,16α,17β-tetrakis(mesyloxy)-8α-estra-1,3,5(10)-triene

반응물

C[C@]12CC[C@@H]3c4c(O)cc(O)cc4CC[C@@H]3[C@@H]1C[C@@H](O)[C@@H]2O
8α-estra-1,3,5(10)-triene-1,3,16α,17β-tetrol
CS(=O)(=O)Cl
methanesulfonic acid chloride
—
ice water

시약

없음

용매

c1ccncc1
pyridine

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    기타is combined at 0° C. with 2 ml
  2. 2
    여과filtered off
  3. 3
    workup.DISSOLUTIONthe residue dissolved in methylene chloride
  4. 4
    기타After purification by chromatography on SiO2, 220 mg

실험 절차

A solution of 400 mg. of 8α-estra-1,3,5(10)-triene-1,3,16α,17β-tetrol in 5 ml. of pyridine is combined at 0° C. with 2 ml. of methanesulfonic acid chloride, and the mixture is agitated for 3 days at 0°-10° C. Thereafter, the mixture is introduced into ice water (acidified with HCl), filtered off, and the residue dissolved in methylene chloride. After purification by chromatography on SiO2, 220 mg. of rac.-1,3,16α,17β-tetrakis(mesyloxy)-8α-estra-1,3,5(10)-triene is obtained.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US03951958uspto-grants-1976_04