Phosphate → 21-deoxyconcanamycin A

HRID 976031Notes

Reaction equation

HRID 976031 reaction equation
[CH3:1][CH2:2][C@@H:3]1[C@H:21]([OH:22])[C@H:20]([CH3:23])[CH:19]=[C:18]([CH3:24])[CH:17]=[C:16]([O:25][CH3:26])[C:14](=[O:15])[O:13][C@H:12]([C@H:27]([C@@H:29]([OH:57])[C@@H:30]([C@:32]2(OC)[O:37][C@H:36](/[CH:38]=[CH:39]/[CH3:40])[C@@H:35]([CH3:41])[C@H:34]([O:42][C@@H:43]3[O:48][C@H:47]([CH3:49])[C@@H:46]([O:50][C:51]([NH2:53])=[O:52])[C@H:45]([OH:54])[CH2:44]3)[CH2:33]2)[CH3:31])[CH3:28])[C@@H:11]([O:58][CH3:59])[CH:10]=[CH:9][CH:8]=[C:7]([CH3:60])[CH2:6][C@@H:5]([CH3:61])[C@@H:4]1[OH:62].[BH3-]C#N.[Na+].CO.O.P([O-])([O-])([O-])=O>CCO>[CH3:1][CH2:2][C@@H:3]1[C@H:21]([OH:22])[C@H:20]([CH3:23])[CH:19]=[C:18]([CH3:24])[CH:17]=[C:16]([O:25][CH3:26])[C:14](=[O:15])[O:13][C@H:12]([C@H:27]([C@@H:29]([OH:57])[C@@H:30]([C@@H:32]2[O:37][C@H:36](/[CH:38]=[CH:39]/[CH3:40])[C@@H:35]([CH3:41])[C@H:34]([O:42][C@@H:43]3[O:48][C@H:47]([CH3:49])[C@@H:46]([O:50][C:51]([NH2:53])=[O:52])[C@H:45]([OH:54])[CH2:44]3)[CH2:33]2)[CH3:31])[CH3:28])[C@@H:11]([O:58][CH3:59])[CH:10]=[CH:9][CH:8]=[C:7]([CH3:60])[CH2:6][C@@H:5]([CH3:61])[C@@H:4]1[OH:62]

Participants

6

Reactant 4

HCID 1061PhosphateHCID 5003444Sodium cyanoborohydrideHCID 11061923O-Methylconcanamycin AHCID 22242641Methanol--water (1/1)

Product 1

HCID 1111555021-deoxyconcanamycin A

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5 ml of 0.5N HCI are added to a solution of 500 mg (0.57 mmol) of 21-O-methylconcanamycin A and 258 mg of NaBH3CN (4.11 mmol, 7 equiv.) in 65 ml of EtOH and the reaction mixture is then stirred at room temperature for 4 hours. The TLC monitoring is effected using RP 8-silica gel plates (Merck) (eluant: MeOH/H2O 9:2). For working-up, 60 ml of phosphate buffer (pH=7) are added, EtOH is removed in vacuo and the aqueous residue is extracted with CHCl3. Purification is carried out by MPLC chromatography on RP 18-silica gel (eluant: MeOH/H2O 8:2). The yield is 228 mg (47%), m.p.: 140° C.

Workup

  1. customEtOH is removed in vacuo
  2. extractionthe aqueous residue is extracted with CHCl3
  3. customPurification

Sources & evidence

ORD record
ord-aa260d5b3ebd462ab4de1d87a75a39e6
Source dataset
uspto-grants-1997_03
Patent number
US05610178

Reaction notes

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