反応 #446677

ord-1a23030e2fde4f88b089973a77d45453

反応方程式

C/C=C(\C)C(=O)O[C@H]1C[C@@H](OC(C)=O)[C@@]2(C(=O)OC)CO[C@H]3[C@@H](O)[C@@](C)([C@]45O[C@@]4(C)[C@H]4C[C@@H]5O[C@@H]5OC=C[C@@]54O)[C@H]4[C@]1(CO[C@]4(O)C(=O)OC)[C@@H]32
Azadirachtin
→
CCC(C)C(=O)O[C@H]1C[C@@H](OC(C)=O)[C@@]2(C(=O)OC)CO[C@H]3[C@@H](O)[C@@](C)([C@]45O[C@@]4(C)[C@H]4CC5O[C@@H]5OCC[C@@]54O)[C@H]4[C@]1(CO[C@]4(O)C(=O)OC)[C@@H]32
2',3',22,23-tetrahydroazadirachtin
収率 59.1%

反応物

C/C=C(\C)C(=O)O[C@H]1C[C@@H](OC(C)=O)[C@@]2(C(=O)OC)CO[C@H]3[C@@H](O)[C@@](C)([C@]45O[C@@]4(C)[C@H]4C[C@@H]5O[C@@H]5OC=C[C@@]54O)[C@H]4[C@]1(CO[C@]4(O)C(=O)OC)[C@@H]32
Azadirachtin

試薬

[Pd]
palladium on alumina

溶媒

CCO
ethanol

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    ろ過The reaction mixture was then filtered
  2. 2
    その他rotary evaporated in vacuo
  3. 3
    その他The crude product was purified by silica gel preparative HPLC (solvent=2-propanol

実験手順

Azadirachtin (30 mg, 0.042 mmol) and 0.5 ml of ethanol was stirred with 20 mg of 5% palladium on alumina at 20° C. under hydrogen (10 atm) for 3 hours. The reaction mixture was then filtered and rotary evaporated in vacuo. The crude product was purified by silica gel preparative HPLC (solvent=2-propanol:n-hexane, 17:83, v/v), followed by ODS preparative HPLC (solvent=methanol:water, 1:1, v/v) to give 2',3',22,23-tetrahydroazadirachtin (18 mg).

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US05001149uspto-grants-1991_03