Milbemectin M.A4 → HCID 101591928, compound

HRID 2081166Notes

Reaction equation

HRID 2081166 reaction equation
[CH3:1][CH2:2][C@H:3]1[O:8][C@:7]2([O:13][C@@H:12]3[CH2:14][CH:15]=[C:16]([CH3:38])[CH2:17][C@@H:18]([CH3:37])[CH:19]=[CH:20][CH:21]=[C:22]4[CH2:23][O:24][C@@H:25]5[C@H:30]([OH:31])[C:29]([CH3:32])=[CH:28][C@@H:27]([C:33]([O:35][C@@H:10]([CH2:11]3)[CH2:9]2)=[O:34])[C@:26]45[OH:36])[CH2:6][CH2:5][C@@H:4]1[CH3:39].CCCCCC.C(COC)[O:47]C>>[CH3:1][CH2:2][C@H:3]1[O:8][C@:7]2([O:13][C@@H:12]3[CH2:14][CH:15]=[C:16]([CH3:38])[C@H:17]([OH:47])[C@@H:18]([CH3:37])[CH:19]=[CH:20][CH:21]=[C:22]4[CH2:23][O:24][C@@H:25]5[C@H:30]([OH:31])[C:29]([CH3:32])=[CH:28][C@@H:27]([C:33]([O:35][C@@H:10]([CH2:11]3)[CH2:9]2)=[O:34])[C@:26]45[OH:36])[CH2:6][CH2:5][C@@H:4]1[CH3:39]

Participants

3

Reactant 2

HCID 9959038Milbemectin M.A4HCID 88399840HCID 88399840, compound

Product 1

HCID 101591928HCID 101591928, compoundYield 70%

Procedure

0.2 g of milbemycin A4 is added to a 2-day-old preculture of S. violascens produced according to H1 in 450 ml of medium 2, and the whole is shaken at 250 rpm. at 28° C. The course of the reaction is monitored by means of HPLC (high pressure liquid chromatography) (column 25 cm/0.5 cm, eluant hexane/dimethoxyethane 3:1, 1 ml/min., UV detector 220 nm). After shaking for 4 days and a 37% conversion rate, 70% 13β-hydroxymilbemycin A4 and 30% 14,15-epoxymilbemycin A4 are obtained.

Workup

  1. customviolascens produced
  2. customat 28° C
  3. stirringAfter shaking for 4 days

Sources & evidence

ORD record
ord-913d327ae87a493c8ddbe86c069f9da1
Source dataset
uspto-grants-1993_02
Patent number
US05183749

Reaction notes

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