Dimethyl Sulfoxide → HCID 101591928, compound

HRID 2081167Notes

Reaction equation

HRID 2081167 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].CS(C)=[O:42]>CCCCCC.C(COC)OC>[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:42])[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

4

Reactant 2

HCID 679Dimethyl SulfoxideHCID 9959038Milbemectin M.A4

Product 1

HCID 101591928HCID 101591928, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 88399840HCID 88399840, compoundSolvent

Procedure

0.25 g of milbemycin A4 and 5 ml of DMSO are added to a 1-day-old culture of S. violascens in 200 ml of medium 3 and the whole is shaken at 250 rpm. at 28° C. After 3 days, a further 50 ml of medium 3 is added. The course of the reaction is monitored by HPLC (column Kontron LiSi 60, 25 cm/0.5 cm, eluant hexane/dimethoxyethane 3:1, 1 ml/min., UV detector 220 nm). After shaking for 7 days and a 91% conversion rate, 92% 13β-hydroxymilbemycin A4 and 8% 14,15-epoxymilbemycin A4 are obtained.

Workup

  1. customat 28° C
  2. additiona further 50 ml of medium 3 is added
  3. stirringAfter shaking for 7 days

Sources & evidence

ORD record
ord-fe7cfeb2a3a3472dafcc269950e59ea3
Source dataset
uspto-grants-1993_02
Patent number
US05183749

Reaction notes

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