Water → HCID 86636761, compound

HRID 522185Notes

Reaction equation

HRID 522185 reaction equation
[CH2:1]([O:8][C@H:9]1[C@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@@H:13]([CH2:23][O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[O:12][C@H:11]([CH2:32][P:33](=[O:40])([O:37][CH2:38][CH3:39])[O:34][CH2:35][CH3:36])[C@@H:10]1[O:41][Si](C(C)(C)C)(C)C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.O>C(Cl)Cl>[CH2:1]([O:8][C@H:9]1[C@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@@H:13]([CH2:23][O:24][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[O:12][C@H:11]([CH2:32][P:33](=[O:40])([O:37][CH2:38][CH3:39])[O:34][CH2:35][CH3:36])[C@@H:10]1[OH:41])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 87229753HCID 87229753, compound

Product 1

HCID 86636761HCID 86636761, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of diethyl (((2S,3R,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-3-((tert-butyldimethylsilyl)oxy)tetrahydro-2H-pyran-2-yl)methyl)phosphonate (3.3 g, 4.72 mmol, 1.0 equiv) in DCM (50 mL) was cooled to 0° C., and a mixture of trifluoroacetic acid and water (3.3 mL/0.33 mL) was added. The reaction mixture was then stirred at room temperature for 16 hours. The mixture was then sequentially washed with saturated aqueous sodium bicarbonate solution (120 mL) and water (100 mL). The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The product thus obtained was purified by silica gel chromatography, eluting with 70% EtOAc in petroleum ether to give diethyl (((2S,3R,4R,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-3-hydroxytetrahydro-2H-pyran-2-yl)methyl)phosphonate as a white solid (2.1 g, 76%). 1H NMR (300 MHz, CDCl3) δ 7.36-7.22 (m, 15H), 4.66-4.56 (m, 3H), 4.52 (s, 2H), 4.41-4.31 (m, 2H), 4.18-4.00 (m, 4H), 3.87-3.70 (m, 4H), 3.67 (td, J=4.1, 1.5 Hz, 1H), 2.24-2.17 (m, 1H), 2.14 (d, J=6.9 Hz, 1H), 1.82-1.67 (m, 2H), 1.34-1.28 (m, 6H). MS (ESI positive ion) m/z: 585.0 (M+1); calc for C32H41O8P 584.3.

Workup

  1. additionwas added
  2. washThe mixture was then sequentially washed with saturated aqueous sodium bicarbonate solution (120 mL) and water (100 mL)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe product thus obtained
  7. customwas purified by silica gel chromatography
  8. washeluting with 70% EtOAc in petroleum ether

Sources & evidence

ORD record
ord-2b40cd7af41144ae9568765a89e32834
Source dataset
uspto-grants-2016_05
Patent number
US09328134B2

Reaction notes

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