HCID 59352489, compound → HCID 59352364, compound

HRID 2385548Notes

Reaction equation

HRID 2385548 reaction equation
CC1(C)[O:38][C@H:5]2[O:6][C@H:7]([CH2:15][N:16]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:18]4([C:36]5[C:27](=[CH:28][C:29]6[O:34][CH2:33][CH2:32][O:31][C:30]=6[CH:35]=5)[O:26][CH2:25]4)[C:17]3=[O:37])[C@@H:8]3[O:12]C(C)(C)[O:10][C@@H:9]3[C@H:4]2[O:3]1>FC(F)(F)C(O)=O>[O:37]=[C:17]1[C:18]2([C:36]3[C:27](=[CH:28][C:29]4[O:34][CH2:33][CH2:32][O:31][C:30]=4[CH:35]=3)[O:26][CH2:25]2)[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:16]1[CH2:15][C@H:7]1[O:6][CH:5]([OH:38])[C@H:4]([OH:3])[C@@H:9]([OH:10])[C@H:8]1[OH:12]

Participants

3

Reactant 1

HCID 59352489HCID 59352489, compound

Product 1

HCID 59352364HCID 59352364, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

1′-{[(3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyltetrahydro-3aH-bis[1,3]dioxolo[4,5-b:4′,5′-d]pyran-5-yl]methyl}-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1′H)-one (0.45 g, 0.83 mmol) was suspended in 80% v/v aqueous trifluoroacetic acid (40 mL) and the reaction mixture was stirred at ambient temperature for 3 h. The reaction mixture was concentrated in vacuo and the residue recrystallized from ethanol to afford 6-deoxy-6-(2′-oxo-2,3-dihydrospiro[furo[2,3-g][1,4]-benzodioxine-8,3′-indol]-1′(2′H)-yl)-D-galactopyranose (0.025 g, 7%) as an off white solid: mp 122-126° C. (ethanol); 13C NMR (75 MHz, CDCl3) δ178.5, 155.2, 155.2, 155.1, 155.0, 144.5, 142.6, 142.2, 142.1, 138.0, 138.0, 132.3, 132.0, 129.0, 123.5, 123.4, 121.0, 120.9, 111.6, 111.4, 109.9, 109.7 99.2, 92.7, 79.9, 64.4, 63.8, 60.4, 58.0, 21.0, 14.2; MS (ES+) m/z 480.0 (M+23).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue recrystallized from ethanol

Sources & evidence

ORD record
ord-069dd817b5834f35a9aba08dcb5cd232
Source dataset
uspto-grants-2012_09
Patent number
US08263606B2

Reaction notes

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