4-aminophenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl)-1-thio-beta-D-glucopyranoside → 4-aminophenyl 4-O-(alpha-D-glucopyranosyl)-1-thio-beta-D-glucopyranoside

HRID 2417862Notes

Reaction equation

HRID 2417862 reaction equation
C([O:4][C@@H:5]1[C@@H:18]([O:19]C(=O)C)[C@H:17]([O:23][C@H:24]2[O:41][C@H:40]([CH2:42][O:43]C(=O)C)[C@@H:35]([O:36]C(=O)C)[C@H:30]([O:31]C(=O)C)[C@H:25]2[O:26]C(=O)C)[C@@H:16]([CH2:47][O:48]C(=O)C)[O:15][C@H:6]1[S:7][C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=1)(=O)C>CO>[C@H:24]1([O:23][C@@H:17]2[C@@H:16]([CH2:47][OH:48])[O:15][C@@H:6]([S:7][C:8]3[CH:9]=[CH:10][C:11]([NH2:14])=[CH:12][CH:13]=3)[C@H:5]([OH:4])[C@H:18]2[OH:19])[O:41][C@H:40]([CH2:42][OH:43])[C@@H:35]([OH:36])[C@H:30]([OH:31])[C@H:25]1[OH:26]

Participants

3

Reactant 1

HCID 132789934-aminophenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl)-1-thio-beta-D-glucopyranoside

Product 1

HCID 542687654-aminophenyl 4-O-(alpha-D-glucopyranosyl)-1-thio-beta-D-glucopyranoside

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 3.5 g portion of 4-aminophenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside was reacted as described in Example 8, giving 1.3 g of the intermediate as a tan solid, [α]D26 =+48°±3° (0.382%, methanol).

Sources & evidence

ORD record
ord-1358437d8ae24a1bbaecd5d700a2b075
Source dataset
uspto-grants-1984_09
Patent number
US04470976

Reaction notes

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