5-Hexyn-1-ol → HCID 86595615, compound

HRID 497721Notes

Reaction equation

HRID 497721 reaction equation
[CH2:1](O)[CH2:2][CH2:3][CH2:4][C:5]#[CH:6].[CH3:8][O:9][C:10]1[CH:46]=[CH:45][C:13]([C:14]([O:29][CH2:30][C@H:31]2[O:35][C@@H:34]([N:36]3[CH:43]=[CH:42][C:40](=[O:41])[NH:39][C:37]3=[O:38])[CH2:33][C@@H:32]2[OH:44])([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)=[CH:12][CH:11]=1>>[CH3:8][O:9][C:10]1[CH:46]=[CH:45][C:13]([C:14]([O:29][CH2:30][C@H:31]2[O:35][C@@H:34]([N:36]3[CH:43]=[CH:42][C:40](=[O:41])[N:39]([CH2:6][CH2:5][CH2:4][CH2:3][C:2]#[CH:1])[C:37]3=[O:38])[CH2:33][C@@H:32]2[OH:44])([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)=[CH:12][CH:11]=1

Participants

3

Reactant 2

HCID 702345-Hexyn-1-olHCID 902301-{5-O-[Bis(4-methoxyphenyl)(phenyl)methyl]-2-deoxypentofuranosyl}-4-hydroxypyrimidin-2(1H)-one

Product 1

HCID 86595615HCID 86595615, compoundYield 86%

Procedure

5-Hexynol was allowed to react with 2′-deoxy-5′-O-(4,4′-dimethoxytrityl)uridine under Mitsunobu conditions described in example 1. Purification on silica gel (eluent diethyl ether) yielded the title compound as a solid (86%) Compound 9:

Workup

  1. customPurification on silica gel (eluent diethyl ether)

Sources & evidence

ORD record
ord-9ab14dc55d284e1485bad44f030fd1e1
Source dataset
uspto-grants-2005_09
Patent number
US06949639B1

Reaction notes

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