A practical silicon-free strategy for differentiation of hydroxy groups in arabinofuranose derivatives

Synthesis

Volumn 44, Issue 8, 2012, Pages 1219-1225

  Abronina, Polina I ^a   Podvalnyy, Nikita M ^a   Sedinkin, Sergey L ^a   Fedina, Ksenia G ^a,b   Zinin, Alexander I ^a   Chizhov, Alexander O ^a   Torgov, Vladimir I ^a   Kononov, Leonid O ^a  

^a N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

^b RUSSIAN ACADEMY OF SCIENCES   (Russian Federation)

Author keywords

acetals; carbohydrates; nucleosides; oligosaccharides; protecting groups

Indexed keywords

ACETALS; ARABINOGALACTAN; BUILDING BLOCKES; GLYCOSYL; HYDROXY GROUPS; LIPOARABINOMANNANS; MYCOBACTERIAL; NOVEL STRATEGIES; NUCLEOSIDE ANALOGUES; NUCLEOSIDES; ORGANOSILICONES; PROTECTING GROUP; SCALE-UP;

BROMINE COMPOUNDS; CARBOHYDRATES; OLIGOSACCHARIDES;

BIOMOLECULES;

1,2 DI O ACETYL 3,5 DI O BENZOYL DEXTRO ARABINOFURANOSE; 3 O (CHLOROACETYL) BETA DEXTRO ARABINOFURANOSE 1,2,5 ORTHOBENZOATE; 3,5 DI O BENZOYL 1,2 BIS O (CHLOROACETYL) DEXTRO ARABINOFURANOSE; 3,5 DI O BENZOYL 1,2 O BENZYLIDINE BETA DEXTRO ARABINOFURANOSE; 3,5 DI O BENZOYL DEXTRO ARABINOFURANOSE; ARABINOFURANOSE DERIVATIVE; ETHYL 1 THIO 3,5 DI O TRITYL ALPHA DEXTRO ARABINOFURANOSIDE; ETHYL 2 O (CHLOROACETYL) 1 THIO ALPHA DEXTRO ARABINOFURANOSIDE; ETHYL 2 O BENZOYL 1 THIO 3,5 DI O TRITYL ALPHA DEXTRO ARABINOFURANOSIDE; ETHYL 2 O BENZOYL 1 THIO ALPHA DEXTRO ARABINOFURANOSIDE; ETHYL 2 O BENZOYL 3,5 BIS O (CHLOROACETYL) 1 THIO ALPHA DEXTRO ARABINOFURANOSIDE; ETHYL 3,5 DI O BENZOYL 2 O (CHLOROACETYL) 1 THIO ALPHA DEXTRO ARABINOFURANOSIDE; HYDROXYL GROUP; OLIGOSACCHARIDE; PHENYL 2 O ACETYL 3,5 DI O BENZOYL 1 THIO ALPHA DEXTRO ARABINOFURANOSIDE; PHENYL 3,5 DI O BENZOYL 1 THIO ALPHA DEXTRO ARABINOFURANOSIDE; PHENYL 3,5 DI O BENZOYL 2 O (CHLOROACETYL) 1 THIO ALPHA DEXTRO ARABINOFURANOSIDE; SILICON; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL COMPOSITION; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 84858711649     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0031-1290752     Document Type: Article

References (22)

1. Joe M, Bai Y, Nacario RC, Lowary TL. J. Am. Chem. Soc.: 2007; 129 9885
2. Zhu X, Kawatkar S, Rao Y, Boons G.-J. J. Am. Chem. Soc.: 2006; 128 11948
3. Ishiwata A, Akao H, Ito Y. Org. Lett.: 2006; 8 5525
4. Lee YJ, Lee K, Jung EH, Jeon HB, Kim KS. Org. Lett.: 2005; 7 3263
5. Crich D, Pedersen CM, Bowers AA, Wink DJ. J. Org. Chem.: 2007; 72 1553
6. Fraser-Reid B, Lu J, Jayaprakash KN, Lpez JC. Tetrahedron: Asymmetry: 2006; 17 2449
7. Liang X.-Y, Deng L.-M, Liu X, Yang J.-S. Tetrahedron: 2010; 66 6687
8. Marotte K, Sanchez S, Bamhaoud T, Prandi J. Eur. J. Org. Chem.: 2003; 3587
9. Yin H, D'Souza FW, Lowary TL. J. Org. Chem.: 2002; 67 892
10. Gadikota RR, Callam CS, Appelmelk BJ, Lowary TL. J. Carbohydr. Chem.: 2003; 22 459
11. Mereyala HB, Hotha S, Gurjar MK. Chem. Commun. (Cambridge): 1998; 685
12. Tam P.-H, Lowary TL. Carbohydr. Chem.: 2010; 36 38; and references cited therein
13. Ness RK, Fletcher HG. J. Am. Chem. Soc.: 1958; 80 2007
14. Callam CS, Lowary TL. J. Chem. Educ.: 2001; 78 73
15. Pathak T. Chem. Rev.: 2002; 102 1623
16. Zatsepin TS, Romanova EA, Oretskaya TS. Russ. Chem. Rev.: 2004; 73 701
17. Antiviral Nucleosides: Chiral Synthesis and Chemotherapy. Chu CK. Elsevier Amsterdam: 2003
18. De Clercq E. Antiviral Res.: 2005; 67 56
19. Matha C, Gosselin G. Antiviral Res.: 2006; 71 276
20. Wuts PG. M, Greene TW. Greene's Protective Groups in Organic Synthesis. 4th ed. Wiley-Interscience Hoboken: 2007; 239
21. Wuts PG. M, Greene TW. Greene's Protective Groups in Organic Synthesis. 4th ed. Wiley-Interscience Hoboken: 2007; 353
22. Kocieski PJ. Protecting Groups. 3rd ed. Thieme Stuttgart: 2005; 171