77855-81-3 → HCID 101591932, compound

HRID 2081168Notes

Reaction equation

HRID 2081168 reaction equation
C[C@@H]1[C@@H](C)O[C@]2([O:10][C@@H]3CC=C(C)C[C@@H](C)C=CC=C4CO[C@@H]5[C@H](O)C(C)=C[C@@H](C(O[C@@H](C3)C2)=O)[C@]45O)CC1.[CH3:39][C@@H:40]1[C@@H:75]([CH:76]([CH3:78])[CH3:77])[O:74][C@:43]2([O:48][C@@H:47]3[CH2:49][CH:50]=[C:51]([CH3:73])[CH2:52][C@@H:53]([CH3:72])[CH:54]=[CH:55][CH:56]=[C:57]4[CH2:58][O:59][C@@H:60]5[C@H:65]([OH:66])[C:64]([CH3:67])=[CH:63][C@@H:62]([C:68]([O:70][C@@H:45]([CH2:46]3)[CH2:44]2)=[O:69])[C@:61]45[OH:71])[CH2:42][CH2:41]1.C[C@@H]1[C@@H](C)O[C@]2(O[C@@H]3CC=C(C)[C@H](O)[C@@H](C)C=CC=C4CO[C@@H]5[C@H](O)C(C)=C[C@@H](C(O[C@@H](C3)C2)=O)[C@]45O)CC1>>[CH3:39][C@@H:40]1[C@@H:75]([CH:76]([CH3:78])[CH3:77])[O:74][C@:43]2([O:48][C@@H:47]3[CH2:49][CH:50]=[C:51]([CH3:73])[C@H:52]([OH:10])[C@@H:53]([CH3:72])[CH:54]=[CH:55][CH:56]=[C:57]4[CH2:58][O:59][C@@H:60]5[C@H:65]([OH:66])[C:64]([CH3:67])=[CH:63][C@@H:62]([C:68]([O:70][C@@H:45]([CH2:46]3)[CH2:44]2)=[O:69])[C@:61]45[OH:71])[CH2:42][CH2:41]1

Participants

4

Reactant 3

HCID 644057977855-81-3HCID 9828343Milbemectin M.A3HCID 101591931HCID 101591931, compound

Product 1

HCID 101591932HCID 101591932, compoundYield 29%

Procedure

If milbemycin A3 or milbemycin D is reacted in an analogous manner, for example at a conversion rate of 10% a ratio of 40% 13β-hydroxymilbemycin A3 and 60% 14,15-epoxymilbemycin A3 is obtained or, at a conversion rate of 13%, a ratio of 29% 13β-hydroxymilbemycin D to 71% 14,15-epoxymilbemycin D is obtained (HPLC analysis).

Workup

  1. customis obtained or, at a conversion rate of 13%

Sources & evidence

ORD record
ord-489d187bbc95423ba9b500c2908563fb
Source dataset
uspto-grants-1993_02
Patent number
US05183749

Reaction notes

Loading…