Tetrabutylammonium Fluoride → 2'-O-(2-Methoxyethyl)-5-methyl-uridine

HRID 2186436Notes

Reaction equation

[Si]([O:18][CH2:19][C@H:20]1[O:24][C@@H:23]([N:25]2[CH:32]=[C:31]([CH3:33])[C:29](=[O:30])[NH:28][C:26]2=[O:27])[C@H:22]([O:34][CH2:35][CH2:36][O:37][CH3:38])[C@@H:21]1[OH:39])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>>[CH3:38][O:37][CH2:36][CH2:35][O:34][C@@H:22]1[C@H:21]([OH:39])[C@@H:20]([CH2:19][OH:18])[O:24][C@H:23]1[N:25]1[CH:32]=[C:31]([CH3:33])[C:29](=[O:30])[NH:28][C:26]1=[O:27]

Participants

Reactant 2

HCID 2724141Tetrabutylammonium Fluoride

HCID 213484835'-O-t-Butyldiphenylsilyl-2'-O-(methoxyethyl)-5-methyluridine

Product 1

HCID 112439882'-O-(2-Methoxyethyl)-5-methyl-uridine

Procedure

5′-O-t-Butyldiphenylsilyl-2′-O-(methoxyethyl)-5-methyluridine is treated with TBAF as per the procedure of Example 8 above to give the title compound.

Sources & evidence

ORD record: ord-a98d5f5482f942d89978c7ef6a376786
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06403779B1

Reaction notes

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