2-Methoxy-6-(tributylstannyl)pyridine → 1-(beta-D-glucopyranosyl)-4-chloro-3-(5-(6methoxy-2-pyridyl)-2-thienylmethyl)benzene

HRID 221018Notes

Reaction equation

HRID 221018 reaction equation
C([O:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@H:9]([O:15]C(=O)C)[C@@H:8]([CH2:19][O:20]C(=O)C)[O:7][C@H:6]1[C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([CH2:31][C:32]2[S:33][C:34](Br)=[CH:35][CH:36]=2)[CH:25]=1)(=O)C.C([Sn](CCCC)(CCCC)[C:43]1[CH:48]=[CH:47][CH:46]=[C:45]([O:49][CH3:50])[N:44]=1)CCC.BrC1C=CC(=O)N(CC2C=CC(CC)=CC=2)C=1>>[C@@H:6]1([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([CH2:31][C:32]3[S:33][C:34]([C:43]4[CH:48]=[CH:47][CH:46]=[C:45]([O:49][CH3:50])[N:44]=4)=[CH:35][CH:36]=3)[CH:25]=2)[O:7][C@H:8]([CH2:19][OH:20])[C@@H:9]([OH:15])[C@H:10]([OH:11])[C@H:5]1[OH:4]

Participants

4

Reactant 3

HCID 105248912-Methoxy-6-(tributylstannyl)pyridineHCID 582425001-(4-ethylbenzyl)-5-bromopyridin-2(1H)-oneHCID 600412891-(2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl)-3-(5bromo-2-thienylmethyl)-4-chlorobenzene

Product 1

HCID 666089171-(beta-D-glucopyranosyl)-4-chloro-3-(5-(6methoxy-2-pyridyl)-2-thienylmethyl)benzene

Procedure

1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3-(5-bromo-2-thienylmethyl)-4-chlorobenzene 71 obtained in Example 128-(4) and tri-n-butyl(6-methoxy-2-pyridyl)tin (see Gros, Philippe; Fort, Yves. Synthesis (1999), 754-756) were treated in a manner similar to Example 128-(5) and (6) to give the target compound. APCI-Mass m/Z 478/480 (M+H).

Workup

  1. customto give the target compound

Sources & evidence

ORD record
ord-c5c29cb4aafc4d17b3cc895bef75ce21
Source dataset
uspto-grants-2012_06
Patent number
US08202984B2

Reaction notes

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