Benzo(b)thiophene-5-carboxaldehyde → 2'-[4-O-(alpha-D-glucopyranosyl)-beta-D-glucopyranosyloxy]-6'-hydroxy-3-(5-benzo[b]thienyl)propiophenone

HRID 355350Notes

Reaction equation

C([O:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@H:9]([O:15][C@H:16]2[O:33][C@H:32]([CH2:34][O:35]C(=O)C)[C@@H:27]([O:28]C(=O)C)[C@H:22]([O:23]C(=O)C)[C@H:17]2[O:18]C(=O)C)[C@@H:8]([CH2:39][O:40]C(=O)C)[O:7][C@H:6]1[O:44][C:45]1[CH:50]=[CH:49][CH:48]=[C:47]([OH:51])[C:46]=1[C:52](=[O:54])[CH3:53])(=O)C.[S:55]1[CH:59]=[CH:58][C:57]2[CH:60]=[C:61]([CH:64]=O)[CH:62]=[CH:63][C:56]1=2>>[C@H:16]1([O:15][C@@H:9]2[C@@H:8]([CH2:39][OH:40])[O:7][C@@H:6]([O:44][C:45]3[CH:50]=[CH:49][CH:48]=[C:47]([OH:51])[C:46]=3[C:52](=[O:54])[CH2:53][CH2:64][C:61]3[CH:62]=[CH:63][C:56]4[S:55][CH:59]=[CH:58][C:57]=4[CH:60]=3)[C@H:5]([OH:4])[C@H:10]2[OH:11])[O:33][C@H:32]([CH2:34][OH:35])[C@@H:27]([OH:28])[C@H:22]([OH:23])[C@H:17]1[OH:18]

Participants

Reactant 2

HCID 139097Benzo(b)thiophene-5-carboxaldehyde

HCID 106052122'-[2,3,6-Tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl)-beta-D-glucopyranosyloxy]-6'-hydroxyacetophenone

Product 1

HCID 186664572'-[4-O-(alpha-D-glucopyranosyl)-beta-D-glucopyranosyloxy]-6'-hydroxy-3-(5-benzo[b]thienyl)propiophenoneYield 51.8%

Procedure

2' -[2,3,6-Tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranosyloxy]-6'-hydroxyacetophenone (1541 mg) and benzo[b]thiophene-5-carbaldehyde (389 mg) are treated in the same manner as in Example 1 to give 2'-[4-O-(α-D-glucopyranosyl)-β-D-glucopyranosyloxy]-6'-hydroxy-3-(5-benzo[b]thienyl)propiophenone (645 mg).

Sources & evidence

ORD record: ord-6c92cb5b82d24d96aa1ebc26b0cd1ee7
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05830873

Reaction notes

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