Highly diastereoselective synthesis of 2'-deoxy[2'-2H]ribonucleoside derivatives by the use of tris(trimethylsilyl)[2H]silane

The use of (Me3Si)3SiH or (Me3Si)3Si2H-Et3B system in place of Bu3SnH or Bu3Sn2H-Et3B system for a reductive protylation or deuteration reaction of 2'-Br-2'-deoxy-3',5'-O-TIPDS-[2'-2H]ribonucleosides or 2'-Br-2'-deoxy-3',5'-O-TIPDS-ribonucleosides was con...

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Bibliographic Details
Published inNucleic acids symposium series (1979) no. 37; pp. 47 - 48
Main Authors Kawashima, E, Uchida, S, Ishido, Y
Format Journal Article
LanguageEnglish
Published England 1997
Subjects
Deoxyribonucleosides - chemical synthesis
Deoxyribonucleosides - chemistry
Deuterium
Indicators and Reagents
Isotope Labeling - methods
Molecular Structure
Silanes
Stereoisomerism
Trimethylsilyl Compounds
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Summary:The use of (Me3Si)3SiH or (Me3Si)3Si2H-Et3B system in place of Bu3SnH or Bu3Sn2H-Et3B system for a reductive protylation or deuteration reaction of 2'-Br-2'-deoxy-3',5'-O-TIPDS-[2'-2H]ribonucleosides or 2'-Br-2'-deoxy-3',5'-O-TIPDS-ribonucleosides was confirmed to improve the reactions to afford an excellent diastereoselectivity, i.e., the diastereoselectivity of (2'S)- or (2'R)-2'-deoxy-[2'-2H]ribonucleosides obtained by the reaction at 0 degree C is equivalent to the diastereoselectivity obtained by that using Bu3SnH or Bu3Sn2H-Et3B system at < -70 degrees C; the reductive deuteration of 2'-O-phenoxythiocarbonyl-3',5'-O-TIPDS-ribonucleosides through (Me3Si)3Si2H-Et3B system at 0 degree C also gave (2'R)-2'-deoxy[2'-2H]ribonucleosides with such a high diastereo-selectivity as above.
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ISSN:0261-3166