SCOPUS 정보 검색 플랫폼

Nucleosides, Nucleotides and Nucleic Acids

Volumn 27, Issue 12, 2008, Pages 1250-1256

Simultaneous removal of benzyl and benzyloxycarbonyl protective groups in 5′-O-(2-deoxy-α-D-glucopyranosyl)uridine by catalytic transfer hydrogenolysis

(3) Wandzik, Ilona a Bieg, Tadeusz a Kadela, Monika a

a SILESIAN UNIVERSITY OF TECHNOLOGY (Poland)

Author keywords

2 deoxy D glucopyranose; Benzyl; Benzyloxycarbonyl protective groups; Hydrogenolysis; Uridine

Indexed keywords

5' O (2 DEOXY ALPHA DEXTRO GLUCOPYRANOSYL)URIDINE; BENZYL DERIVATIVE; CARBONYL DERIVATIVE; N3,2',3' O TRIS(BENZYLOXYCARBONYL)URIDINE; UNCLASSIFIED DRUG; URIDINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; HYDROGENOLYSIS; SYNTHESIS;

BENZYL COMPOUNDS; CATALYSIS; HYDROGEN; HYDROGENATION; MOLECULAR STRUCTURE; URIDINE;

EID: 55949090317 PISSN: 15257770 EISSN: 15322335 Source Type: Journal
DOI: 10.1080/15257770802458303 Document Type: Article

Times cited : (9)

References (13)

1
- 34548120609
- Adducts of uridine and glycals as potential substrates for glycosyltransferases
- Wandzik, I.; Bieg, T. Adducts of uridine and glycals as potential substrates for glycosyltransferases. Bioorg. Chem. 2007, 35, 401-416.
- (2007) Bioorg. Chem , vol.35 , pp. 401-416
- Wandzik, I.¹ Bieg, T.²

2
- 0000234345
- Direct preparation of 2-deoxy-D-glucopyranosides from glycals without Ferrier rearrangement
- Bolitt, V.; Mioskowski, Ch.; Lee, S.-G.; Falck, J.R. Direct preparation of 2-deoxy-D-glucopyranosides from glycals without Ferrier rearrangement. J. Org. Chem. 1990, 55, 5812-5813.
- (1990) J. Org. Chem , vol.55 , pp. 5812-5813
- Bolitt, V.¹ Mioskowski, C.² Lee, S.-G.³ Falck, J.R.⁴

3
- 0036175364
- New methods for the synthesis of N-benzoylated uridine and thymidine derivatives; a convenient method for N-debenzoylation
- Maguire, A.R.; Hladezuk, I.; Ford, A. New methods for the synthesis of N-benzoylated uridine and thymidine derivatives; a convenient method for N-debenzoylation. Carbohydr. Res. 2002, 337, 369-372.
- (2002) Carbohydr. Res , vol.337 , pp. 369-372
- Maguire, A.R.¹ Hladezuk, I.² Ford, A.³

4
- 11444268496
- Facile Deprotection of O-Cbz-Protected Nucleosides by Hydrogenolysis: An Alternative to O-Benzyl Ether-Protected Nucleosides
- Johnson II, D.C.; Widlanski, T.S. Facile Deprotection of O-Cbz-Protected Nucleosides by Hydrogenolysis: An Alternative to O-Benzyl Ether-Protected Nucleosides. Org. Lett. 2004, 4643-4646.
- (2004) Org. Lett , pp. 4643-4646
- Johnson II, D.C.¹ Widlanski, T.S.²

5
- 49949150264
- Noble metal hydroxides on carbon nonpyrophoric dry catalysts
- Pearlman, W.M. Noble metal hydroxides on carbon nonpyrophoric dry catalysts. Tetrahedron Lett. 1967, 17, 1663-1664.
- (1967) Tetrahedron Lett , vol.17 , pp. 1663-1664
- Pearlman, W.M.¹

6
- 0030938293
- An Entry to Unusual Classes of Nucleoside Analogues
- Bar, N.C.; Patra, R.; Achari, B.; Mandal, S.B. An Entry to Unusual Classes of Nucleoside Analogues. Tetrahedron 1997, 53, 4727-4738.
- (1997) Tetrahedron , vol.53 , pp. 4727-4738
- Bar, N.C.¹ Patra, R.² Achari, B.³ Mandal, S.B.⁴

7
- 0011170955
- Synthese und Eigenschvaften von O′-benzyl-substituierten Diuridylphosphaten
- Reitz, G.; Pfleiderer, W. Synthese und Eigenschvaften von O′-benzyl-substituierten Diuridylphosphaten. Chem. Ber. 1975, 108, 2878-2894.
- (1975) Chem. Ber , vol.108 , pp. 2878-2894
- Reitz, G.¹ Pfleiderer, W.²

8
- 0003133973
- Regioselective hydrogenolysis of benzyl glycosides
- Bieg, T.; Szeja, W. Regioselective hydrogenolysis of benzyl glycosides. Carbohydr. Res. 1990, 205, c10-c11.
- (1990) Carbohydr. Res , vol.205
- Bieg, T.¹ Szeja, W.²

9
- 0014913165
- Thio-analogues of 5,6-Dihydrouridine
- Škarić, V.; Gašpert, B.; Hohnjec, M. Thio-analogues of 5,6-Dihydrouridine. J. Chem. Soc. (C). 1970, 2444-2447.
- (1970) J. Chem. Soc. (C) , pp. 2444-2447
- Škarić, V.¹ Gašpert, B.² Hohnjec, M.³

10
- 55949117733
- Procedure for the carbamoylation of uridine (Scheme 3, Trityl chloride (1.37 g, 4.91 mmol) was added to a solution of uridine (1.00 g, 4.09 mmol) in pyridine (5 mL) and reaction mixture was kept at room temperature. After 4 days, the reaction mixture was diluted with CH2Cl2 (300 mL, washed with water (2 x 100 mL, the organic layer was separated, dried (MgSO4, concentrated in vacuo and co-evaporated with toluene (3 x 100 mL, Crude 5′-O-trityluridine (13) was dissolved in CH2Cl2 (15 mL, DIPEA (4.05 ml, 24.54 mmol) was added and solution was cooled to 10°C. A CbzCl (3.50 mL, 24.54 mmol) was added dropwise and the mixture was refluxed for 0.5 hour. The mixture was diluted with CH2Cl2 (100 m, and washed with 1 M HCl and then water. The organic phase was dried (MgSO4) and concentrated. The residue was dissolved in acetonitrile (10 mL) and 48% HBF4 0.65 mL, 4.09 m
- [4]

11
- 0001021477
- Rapid Removal of Protecting Groups from Peptides by Catalytic Transfer Hydrogenation with 1,4-Cyclohexadiene
- Felix, A.M.; Heimer, E.P.; Lambros, T.J.; Tzougraki, C.; Meienhofer, J. Rapid Removal of Protecting Groups from Peptides by Catalytic Transfer Hydrogenation with 1,4-Cyclohexadiene. J. Org. Chem. 1978, 43, 4194-4196.
- (1978) J. Org. Chem , vol.43 , pp. 4194-4196
- Felix, A.M.¹ Heimer, E.P.² Lambros, T.J.³ Tzougraki, C.⁴ Meienhofer, J.⁵

12
- 55949122357
- [1]
- [1]

13
- 55949120946
- Analytical data for new compounds: 5′-O-(2-deoxy-a-D- glucopyranosyl)uridine, 3: solid; [α]D 20+36.0 (MeOH, c 1.0, 1H NMR (300 MHz, CD3OD, δ 1.70 (ddd, 1H, J 3.5, 11.8, 13.2 Hz, H-2″ax, 2.09 (ddd, 1H, J 1.1, 5.0, 13.2 Hz, H-2″eq, 3.26 (t, 1H, J 9.0 Hz, H-4″, 3.53 (ddd, 1H, J 2.3, 5.6, 9.0 Hz, H-5′, 3.67-3.74 (m, 2H, H-6″a,b, 3.79 (ddd, J 5.0, 9.0, 11.8 Hz, H-3″, 3.83 (dd, 1H, J 2.3, 11.5 Hz, H-5′a, 3.94 (dd, 1H, J 2.6, 11.5 Hz, H-5′b, 4.12-4.19 (m, 3H, H-2′, 3′, 4′, 4.99 (br d, 1H, J 3.2 Hz, H-1″, 5.80 (d, J 8.2 Hz, H-5, 5.88 (d, 1H, J 4.1 Hz, H-1′, 7.98 (d, 1H, J 8.2 Hz, H-6, 13C NMR: δ 38.86 (C-2″, 62.87, 67.11, 69.99, 71.32, 73.21, 74.53, 76.12, 84.46 C-2′, C-3′, C-4′, C-5′, C-3″, C-4″
- +): m/z 669.1691, found: m/z 669.1687.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.