Water → (1R,2S,3R,4S,4aR,11bR)-1,3,4,4a,5,11b-Hexahydro-1,2,3,7-tetrahydroxy-4-(phosphonooxy)[1,3]dioxolo[4,5-j]phenanthridin-6(2H)-one

HRID 898740Notes

Reaction equation

HRID 898740 reaction equation
[CH:1]1[C:2]2[C@H:15]3[C@@H:16]([OH:26])[C@H:17]([OH:25])[C@H:18]4[O:23][P:21]([O-:24])(=[O:22])[O:20][C@H:19]4[C@@H:14]3[NH:13][C:11](=[O:12])[C:3]=2[C:4]([OH:10])=[C:5]2[O:9][CH2:8][O:7][C:6]=12.[Na+].[OH2:28]>>[CH:1]1[C:2]2[C@H:15]3[C@@H:16]([OH:26])[C@H:17]([OH:25])[C@@H:18]([OH:23])[C@@H:19]([O:20][P:21]([OH:24])([OH:22])=[O:28])[C@@H:14]3[NH:13][C:11](=[O:12])[C:3]=2[C:4]([OH:10])=[C:5]2[O:9][CH2:8][O:7][C:6]=12

Participants

3

Reactant 2

HCID 962WaterHCID 23673341HCID 23673341, compound

Product 1

HCID 10250687(1R,2S,3R,4S,4aR,11bR)-1,3,4,4a,5,11b-Hexahydro-1,2,3,7-tetrahydroxy-4-(phosphonooxy)[1,3]dioxolo[4,5-j]phenanthridin-6(2H)-one

Procedure

Sodium pancratistatin 3,4-cyclic phosphate (5a, 0.0165 g, 0.04 mmol) was dissolved in water (1 ml) and eluted through a column containing Amberlite IR 120 (H+) resin. The uv active fractions were combined and freeze dried, 0.011 g, 69%, mp. 150° C. (dec). The material was found to be unstable and decomposed over several days. 1H NMR (DMSO-d6, 300 MHz) δ 12.9 (s, 1H), 8.12 (s, 1H), 6.49 (s, 1H), 6.04-6.02 (m, 2H),4.30 (m, 1H), 3.98-3.87 (m, 3H), 3.07-3.01 (m, 1H).

Workup

  1. washeluted through a column
  2. additioncontaining Amberlite IR 120 (H+) resin
  3. customfreeze dried
  4. waitto be unstable and decomposed over several days

Sources & evidence

ORD record
ord-aeef3f7767684a79b2d6e7570e2dbf5c
Source dataset
uspto-grants-2008_04
Patent number
US07351830B2

Reaction notes

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