The patent badge is an abbreviated version of the USPTO patent document. The patent badge does contain a link to the full patent document.

The patent badge is an abbreviated version of the USPTO patent document. The patent badge covers the following: Patent number, Date patent was issued, Date patent was filed, Title of the patent, Applicant, Inventor, Assignee, Attorney firm, Primary examiner, Assistant examiner, CPCs, and Abstract. The patent badge does contain a link to the full patent document (in Adobe Acrobat format, aka pdf). To download or print any patent click here.

Date of Patent:
Apr. 28, 1998

Filed:

Jul. 25, 1995
Applicant:
Inventors:

Suresh C Srivastava, Burlington, MA (US);

Syed Kazim Raza, Waltham, MA (US);

Assignee:

ChemGenes Corporation, Waltham, MA (US);

Attorney:
Primary Examiner:
Assistant Examiner:
Int. Cl.
CPC ...
C07H / ; C07H / ; C07H / ; C07H / ;
U.S. Cl.
CPC ...
536 2623 ; 536 2534 ; 536 2626 ; 536 266 ; 536 267 ; 536 2671 ; 536 276 ; 536 2781 ; 536 285 ; 536 2853 ; 536 231 ; 536 243 ; 536 245 ;
Abstract

The present invention describes a novel 2'-O-alkylation reaction to produce a novel series of nucleosides carrying the 2'-O-propargyl group, using propargyl bromide, dibutyl tin oxide and tetrabutyl ammonium bromide. The procedure involves novel techniques for regioselective introduction of 2'-/3'-O-propargyl group directly on the 5'-DMT-N-protected- nucleosides using dibutyl tin oxide as a mild base in conjunction with a phase transfer catalyst, tetrabutyl ammonium bromide. The reaction process has many significant features and leads to isomeric ratios in favor of the 2'-regio isomer. This allows the synthesis of the corresponding phosphoramidites of high purity.


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