Paclitaxel → 7-Xylosyl-10-deacetyltaxol B

HRID 342163

Reaction equation

HRID 342163 reaction equation
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]

Participants

6

Reactant 2

HCID 36314PaclitaxelHCID 4678379610-Deacetyltaxol 7-Xyloside

Product 3

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c86bfde6c35f4c8597aee6736bb0faba
Source dataset
uspto-grants-1999_01
Patent number
US05856532

Linked notes

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