TY - JOUR
T1 - Synthesis of 5'-O-DMT-2'-O-TBS mononucleosides using an organic catalyst
AU - Lee, Sunggi
AU - Blaisdell, Thomas P.
AU - Kasaplar, Pinar
AU - Sun, Xixi
AU - Tan, Kian L.
N1 - Publisher Copyright:
© 2014 by John Wiley & Sons, Inc.
PY - 2014
Y1 - 2014
N2 - This unit describes a highly effective method to produce 5'-O-DMT-2'-O-TBS mononucleosides selectively using a small organic catalyst. This methodology avoids the tedious protection/deprotection strategy necessary to differentiate the 2'- and 3'-hydroxyl groups in a ribonucleoside. The catalyst was synthesized in two steps, starting from the condensation of valinol and cyclopentyl aldehyde, followed by anionic addition of N-methylimidazole. Ring closure of the amino alcohol with N, N-dimethylformamide dimethyl acetal in methanol furnishes the catalyst. All four 2'-O-TBS protected mononucleosides, U, ABz, GIb, and CAc, were produced in a single step using 10 to 20 mol% of the catalyst at room temperature with excellent yields and selectivity. Further transformation to phosphoramidite demonstrates the utility of this protocol in the preparation of monomers useful for automated synthesis of RNA.
AB - This unit describes a highly effective method to produce 5'-O-DMT-2'-O-TBS mononucleosides selectively using a small organic catalyst. This methodology avoids the tedious protection/deprotection strategy necessary to differentiate the 2'- and 3'-hydroxyl groups in a ribonucleoside. The catalyst was synthesized in two steps, starting from the condensation of valinol and cyclopentyl aldehyde, followed by anionic addition of N-methylimidazole. Ring closure of the amino alcohol with N, N-dimethylformamide dimethyl acetal in methanol furnishes the catalyst. All four 2'-O-TBS protected mononucleosides, U, ABz, GIb, and CAc, were produced in a single step using 10 to 20 mol% of the catalyst at room temperature with excellent yields and selectivity. Further transformation to phosphoramidite demonstrates the utility of this protocol in the preparation of monomers useful for automated synthesis of RNA.
KW - 2'-O-TBS ribonucleosides
KW - Organocatalyst
KW - Phosphoramidation
KW - Protection by site-selective functionalization
UR - http://www.scopus.com/inward/record.url?scp=84949223592&partnerID=8YFLogxK
U2 - 10.1002/0471142700.nc0217s57
DO - 10.1002/0471142700.nc0217s57
M3 - Article
C2 - 24961720
AN - SCOPUS:84949223592
SN - 1934-9270
VL - 2014
SP - 2.17.1-2.17.11
JO - Current Protocols in Nucleic Acid Chemistry
JF - Current Protocols in Nucleic Acid Chemistry
ER -