Reaktion #507008

ord-7b8c0505703d4a199e542ca615e92c33

Reaktionsgleichung

CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1cncc(Br)c1
5-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside
COc1ccncc1B(O)O
4-methoxy-3-pyridineboronic acid
→
COc1ccncc1-c1cncc(O[C@@H]2SC[C@@H](O)[C@H](O)[C@H]2O)c1
desired product
COc1ccncc1-c1cncc(O[C@@H]2SC[C@@H](O)[C@H](O)[C@H]2O)c1
5-(4-Methoxy-3-pyridinyl)-3-pyridinyl 5-thio-β-D-xylopyranoside

Edukte

CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1cncc(Br)c1
5-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside
—
IX
COc1ccncc1B(O)O
4-methoxy-3-pyridineboronic acid

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigeobtained

Vorschrift

By carrying out the operation analogously to example 239, starting from 5-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside, obtained according to preparation IX, and 4-methoxy-3-pyridineboronic acid, the desired product is obtained in the form of a white solid (yield=23%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08093394B2uspto-grants-2012_01