Paclitaxel → 7-Xylosyl-10-deacetyltaxol B

HRID 342163

Reaktionsgleichung

Reaktionsgleichung von HRID 342163
CC1[C@@H](OC([C@H](O)[C@@H](NC(C2C=CC=CC=2)=O)C2C=CC=CC=2)=O)C[C@]2(O)C(C)(C)C=1[C@@H](OC(C)=O)C([C@@]1(C)[C@H]([C@@H]2OC(C2C=CC=CC=2)=O)[C@]2(OC(C)=O)CO[C@@H]2C[C@@H]1O)=O.[CH3:63][C:64]1[C@@H:81]([O:82][C:83]([C@H:85]([OH:102])[C@@H:86]([NH:93][C:94]([C:96]2[CH:101]=[CH:100][CH:99]=[CH:98][CH:97]=2)=[O:95])[C:87]2[CH:92]=[CH:91][CH:90]=[CH:89][CH:88]=2)=[O:84])[CH2:80][C@:76]2([OH:103])[C:77]([CH3:79])([CH3:78])[C:65]=1[C@@H:66]([OH:130])[C:67]([C@@:69]1([CH3:129])[C@@H:74]([C@@H:75]2[O:104][C:105]([C:107]2[CH:112]=[CH:111][CH:110]=[CH:109][CH:108]=2)=[O:106])[C@:73]2([O:115][C:116]([CH3:118])=[O:117])[CH2:113][O:114][C@@H:72]2[CH2:71][C@@H:70]1[O:119][C@@H:120]1[O:125][CH2:124][C@@H:123]([OH:126])[C@H:122]([OH:127])[C@H:121]1[OH:128])=[O:68]>O>[CH3:63][C:64]1[C@@H:81]([O:82][C:83]([C@H:85]([OH:102])[C@@H:86]([NH:93][C:94]([C:96]2[CH:97]=[CH:98][CH:99]=[CH:100][CH:101]=2)=[O:95])[C:87]2[CH:88]=[CH:89][CH:90]=[CH:91][CH:92]=2)=[O:84])[CH2:80][C@:76]2([OH:103])[C:77]([CH3:78])([CH3:79])[C:65]=1[C@@H:66]([OH:130])[C:67]([C@@:69]1([CH3:129])[C@@H:74]([C@@H:75]2[O:104][C:105]([C:107]2[CH:108]=[CH:109][CH:110]=[CH:111][CH:112]=2)=[O:106])[C@:73]2([O:115][C:116]([CH3:118])=[O:117])[CH2:113][O:114][C@@H:72]2[CH2:71][C@@H:70]1[O:119][C@@H:120]1[O:125][CH2:124][C@@H:123]([OH:126])[C@H:122]([OH:127])[C@H:121]1[OH:128])=[O:68].[CH3:98]/[CH:97]=[C:96](/[C:94]([NH:93][C@H:86]([C@@H:85]([OH:102])[C:83]([O:82][C@@H:81]1[C:64]([CH3:63])=[C:65]2[C:77]([CH3:78])([CH3:79])[C@:76]([OH:103])([C@@H:75]([O:104][C:105]([C:107]3[CH:108]=[CH:109][CH:110]=[CH:111][CH:112]=3)=[O:106])[C@@H:74]3[C@:73]4([O:115][C:116]([CH3:118])=[O:117])[CH2:113][O:114][C@@H:72]4[CH2:71][C@H:70]([O:119][C@@H:120]4[O:125][CH2:124][C@@H:123]([OH:126])[C@H:122]([OH:127])[C@H:121]4[OH:128])[C@@:69]3([CH3:129])[C:67]([C@@H:66]2[OH:130])=[O:68])[CH2:80]1)=[O:84])[C:87]1[CH:88]=[CH:89][CH:90]=[CH:91][CH:92]=1)=[O:95])\[CH3:101].[CH3:100][CH2:99][CH2:98][CH2:97][CH2:96][C:94]([NH:93][C@H:86]([C@@H:85]([OH:102])[C:83]([O:82][C@@H:81]1[C:64]([CH3:63])=[C:65]2[C:77]([CH3:78])([CH3:79])[C@:76]([OH:103])([C@@H:75]([O:104][C:105]([C:107]3[CH:112]=[CH:111][CH:110]=[CH:109][CH:108]=3)=[O:106])[C@@H:74]3[C@:73]4([O:115][C:116]([CH3:118])=[O:117])[CH2:113][O:114][C@@H:72]4[CH2:71][C@H:70]([O:119][C@@H:120]4[O:125][CH2:124][C@@H:123]([OH:126])[C@H:122]([OH:127])[C@H:121]4[OH:128])[C@@:69]3([CH3:129])[C:67]([C@@H:66]2[OH:130])=[O:68])[CH2:80]1)=[O:84])[C:87]1[CH:92]=[CH:91][CH:90]=[CH:89][CH:88]=1)=[O:95]

Komponenten

6

Edukt 2

HCID 36314PaclitaxelHCID 4678379610-Deacetyltaxol 7-Xyloside

Produkt 3

HCID 152223117-Xylosyl-10-deacetyltaxol BHCID 152223147-Xylosyl-10-deacetyltaxol CHCID 4678379610-Deacetyltaxol 7-Xyloside

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

According to the first objective of the present invention, an improved process has been developed for isolation of the taxol analogues 7-xylosyl-10-deacetyl taxol A, B, C from the stem bark of Taxus wallichiana in which no solvent partitioning has been used to isolate the analogues. The improved isolation process comprises extracting air dried, pulverized plant materials with alcohols at room temperature, evaporating the solvent to obtain a residue, stirring the resultant residue with water to obtain a thick precipitate, isolating the analogues 7-xylosyl-10-deacetyl-taxol A, 7-xylosyl-10-deacetyl-taxol B and 7-xylosyl-10-deacetyl taxol C from the precipitate by flash chromatography over a bed of silica gel.

Aufarbeitung

  1. custompartitioning
  2. customto isolate the analogues
  3. extractionThe improved isolation process comprises extracting air
  4. customdried
  5. customat room temperature
  6. customevaporating the solvent
  7. customto obtain a residue
  8. customto obtain a thick precipitate

Quellen und Nachweise

ORD-Eintrag
ord-c86bfde6c35f4c8597aee6736bb0faba
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05856532

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