Water → Udp-Galactose

HRID 964702

Reaction equation

HRID 964702 reaction equation
[P:1]([O-:16])([O-:15])([O:3][C@H:4]1[O:12][C@H:11]([CH2:13][OH:14])[C@H:9]([OH:10])[C@H:7]([OH:8])[C@H:5]1[OH:6])=[O:2].[K+].[K+].O.C([NH+](CCCCCCCC)CCCCCCCC)CCCCCCC.C(N(CCCCCCCC)CCCCCCCC)CCCCCCC.C1CCC(NC(N2CCOCC2)=NC2CCCCC2)CC1.C1N([P:97]([O:100][CH2:101][C@H:102]2[O:106][C@@H:105]([N:107]3[C:113](=[O:114])[NH:112][C:110](=[O:111])[CH:109]=[CH:108]3)[C@H:104]([OH:115])[C@@H:103]2[OH:116])([OH:99])=[O:98])CCOC1.N1C=NN=N1>N1C=CC=CC=1>[CH:109]1[C:110](=[O:111])[NH:112][C:113](=[O:114])[N:107]([C@@H:105]2[O:106][C@H:102]([CH2:101][O:100][P:97]([O:2][P:1]([O:3][C@H:4]3[O:12][C@H:11]([CH2:13][OH:14])[C@H:9]([OH:10])[C@H:7]([OH:8])[C@H:5]3[OH:6])([OH:16])=[O:15])([OH:99])=[O:98])[C@@H:103]([OH:116])[C@H:104]2[OH:115])[CH:108]=1

Participants

8

Reactant 6

HCID 962WaterHCID 14227TrioctylamineHCID 87916alpha-D-Galactose 1-(dipotassium phosphate)HCID 3819846TrioctylammoniumHCID 11650518Uridine 5'-monophosphomorpholidate 4-morpholine-N,N'-dicyclohexylcarboxamidine saltHCID 178418441HCID 178418441, compound

Product 1

HCID 18068Udp-GalactoseYield 91%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Dipotassium α-D-galactosyl phosphate (1.0 equivalents, Sigma), containing 5.5 mol H2O, (110 mg, 253 μmol) was converted into the trioctylammonium salt using 110 μL (253 μmol) trioctylamine and reacted with uridine 5'-monophospho morpholidate 4-morpholine-N,N'-dicyclohexylcarboxamidine salt (296 mg, 404 μmol) and 1H-tetrazole (57 mg, 808 μmol) in dry pyridine (1.25 mL) as described for 32. Purification on a Bio-Gel P-2 column (2.5×95 cm), eluated with 250 mM NH4HCO3, and precipitation from H2 O/MeOH/acetone gave 34 (134 mg, 91%) as a white solid after lyophilization (Rf 0.40, 2:1 i-PrOH/1M NH4OAc). The 1H NMR spectral data were in agreement with the published ones (Heidlas et al. J. Org. Chem. 1992, 57, 152-157).

Workup

  1. customPurification on a Bio-Gel P-2 column (2.5×95 cm)
  2. customeluated with 250 mM NH4HCO3, and precipitation from H2 O/MeOH/acetone

Sources & evidence

ORD record
ord-bb1a6ca2dba44221aad9b61dd9c54062
Source dataset
uspto-grants-1998_06
Patent number
US05770407

Linked notes

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