4-(2-Hydroxybenzyl)phenylacetonitrile → 2-(4-Cyanomethylbenzyl)phenyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside

HRID 1247753Notes

Reaction equation

HRID 1247753 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]1OC1C=CC=CC=1C(C)C1C=CC(C#N)=CC=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: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)(=[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

HCID 219092754-(2-Hydroxybenzyl)phenylacetonitrileHCID 865971122-(4-cyano-methylbenzyl)phenyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside

Product 2

HCID 120856172-(4-Cyanomethylbenzyl)phenyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosideHCID 688750182-(4-Cyanomethylbenzyl)Phenyl beta-D-glucopyranoside

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-cyano-methylbenzyl)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-6292d5eb6f9d457081bcf9ee271159d0
Source dataset
uspto-grants-2006_10
Patent number
US07129381B2

Reaction notes

Loading…