Antibiotic DC 11 → aldehydo-L-digitoxose

HRID 67637Notes

Reaction equation

HRID 67637 reaction equation
C[C@@H]1[C@H]2[C@@]3(C)[C@H](C(C)=CC[C@H](O[C@@H]4O[C@H](C)[C@H](NC(OC)=O)[C@]([N+]([O-])=O)(C)C4)C(C)=C[C@H]4[C:23]5([O:31]C(=O)[C:26](=C3O)[C:24]5=[O:25])[CH:22]=[C:21]([CH:32]=[O:33])C[C@@H]4O)C=C[C@@H]2[C@@H]([O:55][C@@H:56]2[O:61][C@@H:60]([CH3:62])[C@H:59]([O:63]C(C)=O)[C@H:58]([O:67][C@@H]3O[C@@H](C)[C@H](O[C@@H]4O[C@@H](C)[C@H](O[C@@H]5O[C@@H](C)[C@H](O)CC5)[C@H](O)C4)CC3)[CH2:57]2)[C@@H](C)C1>C(OCC)(=O)C>[O:33]=[CH:32][CH2:21][CH2:22][C@H:23]([C@H:24]([CH3:26])[OH:25])[OH:31].[O:55]=[CH:56][CH2:57][C@H:58]([C@H:59]([C@H:60]([CH3:62])[OH:61])[OH:63])[OH:67]

Participants

4

Reactant 1

HCID 54681516Antibiotic DC 11

Product 2

HCID 15558782aldehydo-L-digitoxoseHCID 22813088HCID 22813088, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The forementioned studies involved obtaining tetrocarcin A by dissolving DC-11 in ethyl acetate, washing the solution with dilute hydrochloric acid and subjecting the resulting solution to column chromatography using silica gel. The resulting tetrocarcin A is subjected to hydrolysis to obtain L-amicetose, L-digitoxose and a compound represented by the following formula: ##STR2## Based on the physicochemical properties of tetrocarcin A, DC-11 and antlermicin A (the free form of which is considered to be identical to tetrocarcin A; see J. Antibiotics, 33, 244-246, 1980) as shown in Table A below and the results of the hydrolysis above referred to, the above formula for tetrocarcin A was obtained.

Workup

  1. washwashing the solution with dilute hydrochloric acid
  2. customThe resulting tetrocarcin A is subjected to hydrolysis

Sources & evidence

ORD record
ord-4c47697e46b04184a92f2971a4787959
Source dataset
uspto-grants-1982_08
Patent number
US04346075

Reaction notes

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