C[C:2]1([C:8](O)=O)[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.C([N:13]([CH2:16]C)CC)C.P(N=[N+]=[N-])(OC1C=CC=CC=1)(OC1C=CC=CC=1)=[O:19].[OH-].[Na+]>C1(C)C=CC=CC=1>[N:13]([C:2]1([CH3:8])[CH2:3][CH2:4][O:5][CH2:6][CH2:7]1)=[C:16]=[O:19]A stirred solution of 4-methyltetrahydro-2H-pyran-4-carboxylic acid (D9) (1.26 g, 8.74 mmol) in Toluene (50 mL) at room temperature under argon was treated with triethylamine (1.58 mL, 11.36 mmol) and diphenyl azidophosphate (1.88 mL, 8.74 mmol) and heated to 85° C. for 2 hr. The mixture was allowed to cool to room temperature, then treated with 1 M NaOH solution (40 mL) and extracted with Et2O (3×). The combined extract was dried (Na2SO4), filtered and concentrated under vacuum to give the title compound (D10) (520 mg, 34%) as a yellow oil.
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