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Novel approach to diastereoselective synthesis of 2′‐deoxy[5′‐ 2 H 1 ]ribonucleoside derivatives by reduction of the corresponding 5′‐ O ‐acetyl‐2′‐deoxy‐5′‐phenylselenoribonucleoside derivatives with a Bu 3 Sn 2 H‐Et 3 B system
Author(s) -
Kawashima Etsuko,
Toyama Keizo,
Ohshima Kenshiro,
Kainosho Masatsune,
Kyogoku Yoshimasa,
Ishido Yoshiharu
Publication year - 1997
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/(sici)1520-636x(1997)9:5/6<435::aid-chir7>3.0.co;2-4
Subject(s) - chemistry , cytidine , ribonucleoside , chirality (physics) , guanosine , stereochemistry , thymidine , uridine , organic chemistry , enzyme , biochemistry , rna , dna , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , gene , quark
Diastereoselective syntheses of [5′‐ 2 H]thymidine ( 6‐T ) [(5′ R )/(5′ S ) = 31:69], N 4 ‐benzoyl‐2′‐deoxy[5′‐ 2 H]cytidine ( 6‐C Bz ) [(5′ R )/(5′ S ) = 27:76], N 6 ‐benzoyl‐2′‐deoxy[5′‐ 2 H]adenosine ( 6‐A Bz [(5′ R )/(5′ S ) = 39:61], and 2′‐deoxy‐ N 2 ‐isobutyryl[5′‐ 2 H]guanosine ( 6‐G iBu ) [(5′ R )/(5′ S ) = 20:80] were attained by a radical reductive deuteration reaction of the corresponding 5′‐ O ‐acetyl‐3′‐ O ‐TBDMS‐2′‐deoxy‐5′‐phenylselenoribonucleosides ( 4 ) with a Bu 3 Sn 2 H‐Et 3 B system at <−70°C to give 5 (87–98% yields), followed by unmasking (66–79% yields); 4 were synthesized in three steps of reactions from the corresponding 2′‐deoxy‐3′‐ O ‐TBDMS‐5′‐ O ‐Ms‐ribonucleosides ( 1 ) (88–93% yields) by a known method. Chirality 9:435–442, 1997. © 1997 Wiley‐Liss, Inc.