Azadirachtin → HCID 11050687, compound

HRID 727999Notes

Reaction equation

[CH3:1]/[CH:2]=[C:3](/[C:5]([O:7][C@@H:8]1[C@:16]23[C@H:20]([C@@:21]([C@:25]45[O:30][C@@:29]4([CH3:31])[C@@H:28]4[C@:32]6([OH:38])[C@H:36]([O:37][C@H:26]5[CH2:27]4)[O:35][CH:34]=[CH:33]6)([CH3:24])[C@H:22]([OH:23])[C@H:14]4[C@H:15]2[C@:11]([C:44]([O:46][CH3:47])=[O:45])([CH2:12][O:13]4)[C@H:10]([O:48]C(C)=O)[CH2:9]1)[C@@:19]([OH:43])([C:39]([O:41][CH3:42])=[O:40])[O:18][CH2:17]3)=[O:6])\[CH3:4].C[O-].[Na+]>>[CH3:1]/[CH:2]=[C:3](/[C:5]([O:7][C@@H:8]1[C@:16]23[C@H:20]([C@@:21]([C@:25]45[O:30][C@@:29]4([CH3:31])[C@@H:28]4[C@:32]6([OH:38])[C@H:36]([O:37][C@H:26]5[CH2:27]4)[O:35][CH:34]=[CH:33]6)([CH3:24])[C@H:22]([OH:23])[C@H:14]4[C@H:15]2[C@:11]([C:44]([O:46][CH3:47])=[O:45])([CH2:12][O:13]4)[C@H:10]([OH:48])[CH2:9]1)[C@@:19]([OH:43])([C:39]([O:41][CH3:42])=[O:40])[O:18][CH2:17]3)=[O:6])\[CH3:4]

Participants

Reactant 2

HCID 5281303Azadirachtin

HCID 10942334Sodium Methoxide

Product 1

HCID 11050687HCID 11050687, compound

Procedure

Referring to the numbered compounds of Table 1, transesterification of azadirachtin (1) with sodium methoxide gave 3-deacetylazadirachtin (2). Heating a solution of azadirachtin (1) and acetic anhydride at reflux gave a monoacetylated product, 11-O-acetylazadirachtin (4).

Sources & evidence

ORD record: ord-4fc3589893464bbaa2fb59d1bf8363d7
Source dataset: uspto-grants-1991_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05047242

Reaction notes

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