2-(4-Cyanomethylbenzyl)phenyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside → 2-(4-Cyanomethylbenzyl)phenyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside
Reaction equation
[OH:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]#[N:13])=[CH:7][CH:6]=1.[C:18]([O:21][C@@H:22]1[C@@H:44]([O:45][C:46](=[O:48])[CH3:47])[C@H:43]([O:49][C:50](=[O:52])[CH3:51])[C@@H:42]([CH2:53][O:54][C:55](=[O:57])[CH3:56])[O:41][C@H:23]1[O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH2:31][C:32]1[CH:37]=[CH:36][C:35]([CH2:38][C:39]#[N:40])=[CH:34][CH:33]=1)(=[O:20])[CH3:19]>>[C:18]([O:21][C@@H:22]1[C@@H:44]([O:45][C:46](=[O:48])[CH3:47])[C@H:43]([O:49][C:50](=[O:52])[CH3:51])[C@@H:42]([CH2:53][O:54][C:55](=[O:57])[CH3:56])[O:41][C@H:23]1[O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH2:31][C:32]1[CH:33]=[CH:34][C:35]([CH2:38][C:39]#[N:40])=[CH:36][CH:37]=1)(=[O:20])[CH3:19].[O:1]([C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]#[N:13])=[CH:7][CH:6]=1)[C@@H:23]1[O:41][C@H:42]([CH2:53][OH:54])[C@@H:43]([OH:49])[C@H:44]([OH:45])[C@H:22]1[OH:21]Participants
4
Reactant 2
Product 2
Procedure
2-(4-Cyanomethylbenzyl)phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside was prepared in a similar manner to that described in Reference Example 8 using 4-(2-hydroxybenzyl)phenylacetonitrile instead of methyl 4-(2-hydroxybenzyl)benzoate. Then the title compound was prepared in a similar manner to that described in Example 2 using 2-(4-cyanomethylbenzyl)phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside instead of 2-(4-methoxycarbonylbenzyl)phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside.
Sources & evidence
- ORD record
- ord-b134f9ebd9e342ab9dfc461d0e4f6b9c
- Source dataset
- uspto-grants-2006_05
- Patent number
- US07053060B2
Reaction notes
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