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Synthesis of antisense oligodeoxyribonucleotide analogues by use of deoxyribonucleoside 3′-bis(1, 1, 1, 3,3,3-hexafluoro-2-propyl) phosphites as new key intermediates

✍ Scribed by Hideo Hosaka; Testuo Watanabe; Yoshikazu Suzuki; Hiroshi Takaku

Publisher: John Wiley and Sons
Year: 1991
Tongue: English
Weight: 609 KB
Volume: 2
Category: Article
ISSN: 1042-7163
DOI: 10.1002/hc.520020122

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✦ Synopsis

The deoxyribonucleoside 3'-bis(l ,I ,I ,3,3,3-hexafluoro-2-propyl) phosphite units (3) are used in the chemical synthesis of oligodeoxyribonucleotides on solid supports. The new phosphite units (3) were prepared easily by reaction of nucleosides and tris-( I ,I ,I ,3,3,3-hexafluoro-2-propyl) phosphite (2). They are readily activated by N-methylimidazole under very mild conditions on a solid support. This operation involves a one step reaction, which is an advantage over both the phosphite and H-phosphonate ap-

proaches. The use of deoxyribonucleoside phosph ite intermediates in the synthesis of antisense oligodeoxyribonucleotides is also described.

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