Uridine → Uridine

HRID 926229Notes

Reaction equation

HRID 926229 reaction equation
NOC[O:4][C@@H:5]1[C@H:9]([OH:10])[C@@H:8]([CH2:11][OH:12])[O:7][C@H:6]1[N:13]1[CH:20]=[CH:19][C:17](=[O:18])[NH:16][C:14]1=[O:15].C=C(CCC[C@H]([C@@H]1[C@]2(C)[C@H]([C@H]3[C@H](CC2)[C@]2(C)C(CC(=O)CC2)CC3)CC1)C)C.S(Cl)(C1C2C=CC=C(N(C)C)C=2C=CC=1)(=O)=O.[C@@H]1(N2C=CC(=O)NC2=O)O[C@H](CO)[C@@H](O)[C@H]1O.[CH3:83][CH2:84][CH2:85][CH2:86][N+:87]([CH2:96][CH2:97][CH2:98][CH3:99])([CH2:92][CH2:93][CH2:94][CH3:95])[CH2:88][CH2:89][CH2:90][CH3:91].[F-:100].C1COCC1.[C@@H]1(N2C=CC(N)=NC2=O)O[C@H](CO)[C@@H](O)[C@H]1O>C1COCC1>[CH3:95][CH2:94][CH2:93][CH2:92][N+:87]([CH2:96][CH2:97][CH2:98][CH3:99])([CH2:86][CH2:85][CH2:84][CH3:83])[CH2:88][CH2:89][CH2:90][CH3:91].[F-:100].[C@@H:6]1([N:13]2[CH:20]=[CH:19][C:17](=[O:18])[NH:16][C:14]2=[O:15])[O:7][C@H:8]([CH2:11][OH:12])[C@@H:9]([OH:10])[C@H:5]1[OH:4]

Participants

9

Reactant 6

HCID 6029Uridine2×HCID 6175CytidineHCID 11801Dansyl chlorideHCID 11078149TBAF tetrahydrofuranHCID 66769821HCID 66769821, compoundHCID 70818775HCID 70818775, compound

Product 2

HCID 6029UridineHCID 2724141Tetrabutylammonium Fluoride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In contrast to the oximation of aldehydes with 5a, its reaction with cholesten-3-one (7) and dansyl chloride gave, as expected, the permanent uridine 2′-conjugates 8 and 19, respectively. These conjugates were both found stable to TBAF/THF under the conditions used for the conversion of 6a-d, 10, 12, 14, and 16 to uridine or cytidine. Indeed, treatment of 19 with 0.5 M TBAF in THF for 72 h at 55° C. produced uridine to the extent of less than 1%, as determined by RP-HPLC analysis of the reaction products.

Workup

  1. customgave

Sources & evidence

ORD record
ord-5baad893392e4b5599db6434d69a7f7c
Source dataset
uspto-grants-2016_03
Patent number
US09284343B2

Reaction notes

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