Electrophilic glycosidation employing 3,5-O-(di-tert-butylsilylene)-erythro-furanoid glycal leads to exclusive formation of the β-anomer: synthesis of 2′-deoxynucleosides and its 1′-branched analogues

Tetrahedron

Volumn 66, Issue 25, 2010, Pages 4587-4600

  Haraguchi, Kazuhiro ^a   Konno, Kiju ^a   Yamada, Kaori ^a   Kitagawa, Yasuyuki ^a   Nakamura, Kazuo T ^a   Tanaka, Hiromichi ^a  

^a SHOWA UNIVERSITY   (Japan)

Author keywords

Electrophilic glycosidation; Glycal; Lithiation; Nucleoside

Indexed keywords

1 [3,5 BIS O (TERT BUTYLDIMETHYLSILYL) 2 DEOXY 2 IODO BETA D RIBOFURANOSYL]THYMINE; 1 [3,5 BIS O (TERTBUTYLDIMETHYLSILYL) 2 DEOXY 2 IODO ALPHA D RIBOFURANOSYL]THYMINE; 1 [3,5 O (1,1,3,3 TETRAISOPROPYLDISILOXANE 1,3 DIYL) 2 DEOXY 2 IODO ALPHA D RIBOFURANOSYL]THYMINE; 1 [3,5 O (1,1,3,3 TETRAISOPROPYLDISILOXANE 1,3 DIYL) 2 DEOXY 2 IODO BETA D RIBOFURANOSYL]THYMINE; 1 [3,5 O (DI TERT BUTYLSILYLENE) 2 DEOXY 2 IODO BETA D RIBOFURANOSYL]THYMINE; 1 [3,5 O (DI TERT BUTYLSILYLENE) 2 DEOXY 2 IODO BETA D RIBOFURANOSYL]URACIL; 1 [3,5 O (DI TERT BUTYLSILYLENE) 2 DEOXY BETA D RIBOFURANOSYL]THYMINE; 1 [3,5 O (DI TERT BUTYLSILYLENE) 2 DEOXY BETA D RIBOFURANOSYL]URACIL; 1,4 ANHYDRO 1 C BENZYL 2 DEOXY 3,5 DI O (DI TERTBUTYLSILYLENE) D ERYTHRO PENT 1 ENITOL; 1,4 ANHYDRO 2 DEOXY 3,5 BIS O (DI TERT BUTYLSILYLENE) 1 C HYDROXYMETHYL D ERYTHRO PENT 1 ENITOL; 1,4 ANHYDRO 2 DEOXY 3,5 BIS O (DI TERT BUTYLSILYLENE) 1 C METHYL D ERYTHRO PENT 1 ENITOL; 1,4 ANHYDRO 2 DEOXY 3,5 DI O (DI TERT BUTYLSILYLENE) 1 C (ALPHA HYDROXYBENZYL) D ERYTHRO PENT 1 ENITOL; 1,4 ANHYDRO 2 DEOXY 3,5 O (1,1,3,3 TETRAISOPROPYLD ISILOXANE 1,3 DIYL) D ERYTHRO PENT 1 ENTIOL; 1,4 ANHYDRO 2 DEOXY 3,5 O (DI TERT BUTYLSILYLENE) D ERYTHRO PENT 1 ENTIOL; 2' DEOXYNUCLEOSIDE; 2,4 BIS O (TRIMETHYLSILYL)THYMINE; 3,5 O (DI T BUTYLSILYLENE); 3,5 O (DI TERT BUTYLSILYLENE) ERYTHRO FURANOID GLYCAL; FURAN DERIVATIVE; N4 ACETYL 1 [3,5 O (DI TERT BUTYLSILYLENE) 2 DEOXY 2 IODO BETA D RIBOFURANOSYL] CYTOSINE; N4 ACETYL 1 [3,5 O (DI TERT BUTYLSILYLENE) 2 DEOXY BETA D RIBOFURANOSYL] CYTOSINE; N6 BENZOYL 1 [3,5 O (DI TERT BUTYLSILYLENE) 2 DEOXY 2 IODO BETA D RIBOFURANOSYL]ADENINE; N6 BENZOYL 7 [3,5 O (DI TERTBUTYLSILYLENE) 2 DEOXY 2 IODO BETA D RIBOFURANOSYL]ADENINE; N6 BENZOYL 9 [3,5 O (DI TERT BUTYLSILYLENE) 2 DEOXY 2 IODO BETA D RIBOFURANOSYL]ADENINE; N6 BENZOYL 9 [3,5 O (DI TERT BUTYLSILYLENE) 2 DEOXY BETA D RIBOFURANOSYL] ADENINE; PHENYL 3,5 O (1,1,3,3 TETRAISOPROPYLDISILOXANE 1,3 DIYL) 2 DEOXY 1 THIO D ERYTHRO PENTOFURANOSE S OXIDE; PHENYL 3,5 O (1,1,3,3 TETRAISOPROPYLDISILOXANE 1,3 DIYL) 2 DEOXY 1 THIO D ERYTHRO PENTOFURANOSIDE; PHENYL 3,5 O (DI TERT BUTYLSILYLENE) 1THIO D ERYTHRO PENTOFURANOSIDE; SILANE DERIVATIVE; THYMINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; GLYCOSIDATION; PRIORITY JOURNAL; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 77953122964     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.04.043     Document Type: Article

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