Sodium Methoxide → 4-(4-cyanophenyl)phenyl 1,5-dithio-beta-D-xylopyranoside

HRID 6017Notes

Reaction equation

HRID 6017 reaction equation
C([O:4][C@@H:5]1[C@@H:25]([O:26]C(=O)C)[C@H:24]([O:30]C(=O)C)[CH2:23][S:22][C@H:6]1[S:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][CH:15]=2)=[CH:10][CH:9]=1)(=O)C.C[O-].[Na+]>>[S:7]([C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][CH:15]=2)=[CH:12][CH:13]=1)[C@@H:6]1[S:22][CH2:23][C@@H:24]([OH:30])[C@H:25]([OH:26])[C@H:5]1[OH:4]

Participants

3

Reactant 2

HCID 10942334Sodium MethoxideHCID 147953594-(4-cyanophenyl)phenyl 2,3,4-tri-O-acetyl-1,5-dithio-beta-D-xylopyranoside

Product 1

HCID 147953914-(4-cyanophenyl)phenyl 1,5-dithio-beta-D-xylopyranosideYield 80%

Procedure

If the procedure described in Preparation V is followed starting from 0.340 g (70.1.10-3 mol) of 4-(4-cyanophenyl)phenyl 2,3,4-tri-O-acetyl-1,5-dithio-β-D-xylopyranoside (Example 14a) and 17 ml of sodium methylate (8% w/v solution of Na in methanol), 0.200 g (yield: 80%) of the expected product is obtained after purification by recrystallization from methanol.

Workup

  1. customIf the procedure described in Preparation V

Sources & evidence

ORD record
ord-37b7bb1ecdf94502af5f9622197b3b7e
Source dataset
uspto-grants-1993_09
Patent number
US05246961

Reaction notes

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