D-Psicose → HCID 66916049, compound

HRID 227167Notes

Reaction equation

HRID 227167 reaction equation
C([O:8][C:9]1[C:10]([O:42][CH3:43])=[CH:11][C:12]2[N:18]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C@@H:17]([O:26][CH:27]3[C:32]([OH:33])=[C:31]([OH:34])[C:30]([OH:35])=[C:29]([OH:36])[O:28]3)[C@@H:16]3[CH2:37][CH2:38][CH2:39][N:15]3[C:14](=[O:40])[C:13]=2[CH:41]=1)C1C=CC=CC=1.OCC1(OC[C@@H](O)[C@@H](O)[C@H]1O)O>[Pd].CCOC(C)=O.CCCCCC>[C:22]([O:21][C:19]([N:18]1[C:12]2[CH:11]=[C:10]([O:42][CH3:43])[C:9]([OH:8])=[CH:41][C:13]=2[C:14](=[O:40])[N:15]2[CH2:39][CH2:38][CH2:37][C@H:16]2[C@@H:17]1[O:26][CH:27]1[C:32]([OH:33])=[C:31]([OH:34])[C:30]([OH:35])=[C:29]([OH:36])[O:28]1)=[O:20])([CH3:25])([CH3:23])[CH3:24]

Participants

5

Reactant 2

HCID 441036D-PsicoseHCID 66916099HCID 66916099, compound

Product 1

HCID 66916049HCID 66916049, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21226206Ethyl acetate hexaneSolvent

Procedure

A catalytic amount of 10% palladium on carbon (380 mg) was added to a solution of THP protected compound 6 (3.8 g, 7 mmol) in absolute alcohol (30 mL). The reaction mixture was hydrogenated for 3 h at 35 Psi. When the reaction was complete as indicated by TLC (SiO2, 50% EtOAc-hexane) the reaction mixture was filtered through Celite, and removal of excess solvent under reduced pressure afforded the phenol 7 (2.8 g, 6.25 mmol, 90% yield, mixture of diastereomers from THP protecting group) as a white solid: [α]20D=+52° (c=0.183, CHCl3); 1H NMR (CDCl3, 400 MHz): δ 1.35 (s, 18H, Boc), 1.48-1.68 (m, 6H, THP), 1.69-1.88 (m, 6H, THP), 1.91-2.18 (m, 8H, 1-H, 2-H), 3.44-3.75 (m, 8H, 3-H, 11a-H, THP), 3.84-4.02 (m, 8H, 7-OMe, THP), 4.96-5.09 (m, 1H, THP), 5.10-5.18 (m, 1H, THP), 5.69-5.76 (d, 1H, 11-H), 5.77-5.87 (d, 1H, 11-H), 6.03 (s, 1H, OH), 6.14 (s, 1H, OH), 6.49 (s, 1H, 9-H), 6.86 (s, 1H, 9-H), 7.28 (s, 1H, 6-H), 7.32 (s, 1H, 6-H); 13C NMR (CDCl3, 400 MHz): δ 19.8, 20.5, 23.1, 23.2, 25.2, 25.3, 28.1, 28.2, 28.8, 29.1, 30.8, 31.2, 46.2, 55.9, 56.1, 59.9, 60.1, 63.3, 64.6, 80.9, 88.1, 91.1, 95.2, 100.4, 112.6, 113.3, 113.6, 114.2, 127.1, 129.0, 145.0, 145.3, 148.1, 148.5, 155.1, 167.1, 167.3; IR (neat): 3306, 2946, 1703, 1632, 1511, 1453, 1394, 1368, 1334, 1274, 1212, 1163, 1116, 1023 cm−1; MS (FAB) m/z (relative intensity) 471 ([M+Na]+., 5), 449 (M+., 100), 246 (50), 393 (22).

Workup

  1. filtrationwas filtered through Celite, and removal of excess solvent under reduced pressure

Sources & evidence

ORD record
ord-1a06a480d7994f4a9bf65aa4151265b3
Source dataset
uspto-grants-2009_07
Patent number
US07557099B2

Reaction notes

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