HCID 11377493, compound → HCID 11296996, compound

HRID 555224Notes

Reaction equation

HRID 555224 reaction equation
CCCCCCCCCCCCCCCC(N[C@H]([C@H](O)/C=C/CCCCCCCCCCC)CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)=O.[CH3:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][C:65]([NH:67][C@H:68]([C@H:82]([OH:96])/[CH:83]=[CH:84]/[CH2:85][CH2:86][CH2:87][CH2:88][CH2:89][CH2:90][CH2:91][CH2:92][CH2:93][CH2:94][CH3:95])[CH2:69][O:70][C@@H:71]1[O:76][C@H:75]([CH2:77][OH:78])[C@@H:74]([OH:79])[C@H:73]([OH:80])[C@H:72]1[OH:81])=[O:66]>>[CH3:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][C:65]([NH:67][C@H:68]([C@H:82]([OH:96])/[CH:83]=[CH:84]/[CH2:85][CH2:86][CH2:87][CH2:88][CH2:89][CH2:90][CH2:91][CH2:92][CH2:93][CH2:94][CH3:95])[CH2:69][O:70][C@@H:71]1[O:76][C@H:75]([CH2:77][OH:78])[C@H:74]([OH:79])[C@H:73]([OH:80])[C@H:72]1[OH:81])=[O:66]

Participants

3

Reactant 2

HCID 11377493HCID 11377493, compoundHCID 11456614HCID 11456614, compound

Product 1

HCID 11296996HCID 11296996, compound

Procedure

Turbostatins 1 and 2 were obtained in the following order: Turbostatin 1 (10.1 mg) at 20.5 minutes and turbostatin 2 (11.2 mg) at 25.1 minutes. A103-mg fraction with ED50 0.56 μg/mL was separated on a semipreparative reversed-phase HPLC Zorbax SB C18 column with 85:15 CH3OH—H2O (a flow rate of 4 mL/min and the UV detector set at 208 nm). The result was that turbostatin 3 and turbostatin 4 were obtained in the following order: turbostatin 3 at 23.7 minutes and turbostatin 4 (8.3 mg) at 28.5 minutes.

Workup

  1. customTurbostatins 1 and 2 were obtained in the following order
  2. customA103-mg fraction with ED50 0.56 μg/mL was separated on a semipreparative reversed-phase HPLC Zorbax SB C18 column with 85:15 CH3OH—H2O (a flow rate of 4 mL/min

Sources & evidence

ORD record
ord-2d01a7a102034114a9cff23b3c5450d7
Source dataset
uspto-grants-2011_11
Patent number
US08053416B2

Reaction notes

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