Synthesis of glycosides of 3-deoxy-4-thiopentopyranosid-2-uloses and their reduction products: 3-Deoxy-4-thiopentopyranosides
Michael addition of common thiols to the enone system of (2S)-2-benzyloxy-2H-pyran-3(6H)-one (1) afforded the corresponding 3-deoxy-4-thiopentopyranosid-2-ulose derivatives (2-4). The reaction was highly diastereoselective, and the addition was governed by the quasiaxially disposed 2-benzyloxy subst...
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2002
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| Acceso en línea: | Registro en Scopus DOI Handle Registro en la Biblioteca Digital |
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| LEADER | 08446caa a22012137a 4500 | ||
|---|---|---|---|
| 001 | PAPER-20260 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518205139.0 | ||
| 008 | 190411s2002 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-0037137271 | |
| 024 | 7 | |2 cas |a Glycosides; Pentoses; Sulfhydryl Compounds; Thioglycosides | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a CRBRA | ||
| 100 | 1 | |a Uhrig, M.L. | |
| 245 | 1 | 0 | |a Synthesis of glycosides of 3-deoxy-4-thiopentopyranosid-2-uloses and their reduction products: 3-Deoxy-4-thiopentopyranosides |
| 260 | |c 2002 | ||
| 270 | 1 | 0 | |m Varela, O.; Departamento de Quimica Organica, Facultad de Cie. Exactas y Naturales, Universidad de Buenos Aires, 1428 Buenos Aires, Argentina; email: varela@qo.fcen.uba.ar |
| 506 | |2 openaire |e Política editorial | ||
| 504 | |a Witczak, Z.J., (1999) Curr. Med. Chem., 6, pp. 165-178 | ||
| 504 | |a Becker, B., (2000) J. Carbohydr. Chem., 19, pp. 253-284 | ||
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| 504 | |a Essig, M.G., (1986) Carbohydr. Res., 156, pp. 225-231 | ||
| 504 | |a Gomez, M., Quincoces, J., Kuhla, B., Peseke, K., Reinke, H., (1999) J. Carbohydr. Chem., 18, pp. 57-68 | ||
| 504 | |a Michael, K., Kessler, H., (1996) Tetrahedron Lett., 37, pp. 3453-3456 | ||
| 504 | |a Witczak, Z.J., Sun, J., Mielguj, R., (1995) Bioorg. Med. Chem. Lett., 5, pp. 2169-2174 | ||
| 504 | |a Witczak, Z.J., Chhabra, R., Chen, H., Xie, X.-Q., (1997) Carbohydr. Res., 301, pp. 167-175. , and references therein | ||
| 504 | |a Kroutil, J., Cerný, M., Trnka, T., Budešínsky, M., (2001) Carbohydr. Res., 334, pp. 153-158 | ||
| 504 | |a Witczak, Z.J., Chen, H., Kaplon, P., (2000) Tetrahedron: Asymmetry, 11, pp. 519-532 | ||
| 504 | |a Gomez, M., Quincoces, J., Peseke, K., Michalik, M., Reinke, H., (1999) J. Carbohydr. Chem., 18, pp. 851-865 | ||
| 504 | |a De Fina, G., Varela, O., Lederkremer, R.M., (1988) Synthesis, pp. 891-893 | ||
| 504 | |a Iriarte-Capaccio, C., Varela, O., (2001) J. Org. Chem., 66, pp. 8859-8866 | ||
| 504 | |a Varela, O., De Fina, G., Lederkremer, R.M., (1993) Carbohydr. Res., 246, pp. 371-376 | ||
| 504 | |a Varela, O., De Fina, G., Lederkremer, R.M., (1990) J. Chem. Res. (S), pp. 262-263 | ||
| 504 | |a Zunszain, P.A., Varela, O., (1998) Tetrahedron: Asymmetry, 9, pp. 1269-1276 | ||
| 504 | |a Iriarte-Capaccio, C., Varela, O., (2000) Tetrahedron: Asymmetry, 11, pp. 4945-4954 | ||
| 504 | |a Uhrig, M.L., Varela, O., (2002) Aust. J. Chem., 55, pp. 155-160 | ||
| 504 | |a Dauben, W.G., Kowalczyk, B.A., Lichtenthaler, F.W., (1990) J. Org. Chem., 55, pp. 2391-2398 | ||
| 504 | |a Horton, D., Durette, P.L., Wander, J., (1973) Ann. NY Acad. Sci., 222, pp. 884-914 | ||
| 504 | |a Durette, P.L., Horton, D., (1971) Adv. Carbohydr. Chem. Biochem., 26, pp. 49-125 | ||
| 504 | |a Lichtenthaler, F.W., Nishiyama, S., Köhler, P., Linder, H.J., (1985) Carbohydr. Res., 136, pp. 13-26 | ||
| 504 | |a Bock, K., Pedersen, C., (1983) Adv. Carbohydr. Chem. Biochem., 41, pp. 27-66 | ||
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| 520 | 3 | |a Michael addition of common thiols to the enone system of (2S)-2-benzyloxy-2H-pyran-3(6H)-one (1) afforded the corresponding 3-deoxy-4-thiopentopyranosid-2-ulose derivatives (2-4). The reaction was highly diastereoselective, and the addition was governed by the quasiaxially disposed 2-benzyloxy substituent of the starting pyranone. As expected from the enantiomeric excess of 1 (ee >86%) the corresponding thiouloses 2-4 exhibited the same optical purity. However, the enantiomerically pure thioulose 5 was obtained by reaction of 1 with the chiral thiol, N-(tert-butoxycarbonyl)-L-cysteine methyl ester. The thio derivative 7 was also synthesized by reaction of 6 (enantiomer of 1) with the same chiral thiol. Alternatively, 4-thiopent-2-uloses 9-12 were prepared in high optical purity by 1,4-addition of thiols to (2S)-[(S)-2′-octyloxy]dihydropyranone 8. Similarly, reaction of 13 (enantiomer of 8) with benzenemethanethiol afforded 14 (enantiomer of 10). This way, the stereocontrol exerted by the anomeric center on the starting dihydropyranone led to 4-thiopentuloses of the D and L series. Sodium borohydride reduction of the carbonyl function of uloses 10 and 12 gave the corresponding 3-deoxy-4-thiopentopyranosid-2-uloses (16-19). The diastereomers having the β-D-threo configuration (16, 18) slightly predominated over the β-D-erythro (17, 19) analogues. However, the reduction of the enantiomeric pyranones 10 and 14 with K-Selectride® was highly diastereofacial selective in favor of the β-D- and β-L-threo isomers 16 and 20, respectively. © 2002 Elsevier Science Ltd. All rights reserved. |l eng | |
| 536 | |a Detalles de la financiación: Universidad de Buenos Aires, X108 | ||
| 536 | |a Detalles de la financiación: Consejo Nacional de Investigaciones Científicas y Técnicas | ||
| 536 | |a Detalles de la financiación: Financial support from the University of Buenos Aires (Project X108) and from The National Research Council of República Argentina (CONICET) is gratefully acknowledged. O. V. is a Research Member of CONICET. | ||
| 593 | |a CIHIDECAR-CONICET, Departamento De Química Orgánica, Niversidad De Buenos Aires, 1428, Buenos Aires, Argentina | ||
| 690 | 1 | 0 | |a 3-DEOXY-4-THIOPENTOPYRANOSID-2-ULOSES |
| 690 | 1 | 0 | |a 3-DEOXY-4-THIOPENTOPYRANOSIDES |
| 690 | 1 | 0 | |a MICHAEL ADDITION |
| 690 | 1 | 0 | |a THIO SUGARS |
| 690 | 1 | 0 | |a ADDITION REACTIONS |
| 690 | 1 | 0 | |a DERIVATIVES |
| 690 | 1 | 0 | |a ESTERS |
| 690 | 1 | 0 | |a ISOMERS |
| 690 | 1 | 0 | |a STEREOCHEMISTRY |
| 690 | 1 | 0 | |a SYNTHESIS (CHEMICAL) |
| 690 | 1 | 0 | |a STEREOCONTROLS |
| 690 | 1 | 0 | |a CARBOHYDRATES |
| 690 | 1 | 0 | |a 2 OCTYL 2 O ACETYL 3 DEOXY 4 S [METHYL N (TERT BUTOXYCARBONYL)CYSTEINAT 3 YL] 4 THIO BETA DEXTRO THREO BETA DEXTRO ERYTHRO PENTAPYRANOSIDE |
| 690 | 1 | 0 | |a 2 OCTYL 3 DEOXY 4 S [METHYL N (TERT BUTOXYCARBONYL)CYSTEINAT 3 YL] 4 THIO BETA DEXTRO GLYCEROPENTOPYRANOSID 2 ULOSE |
| 690 | 1 | 0 | |a 2 OCTYL 3 DEOXY 4 S ETHYL 4 THIO BETA DEXTRO GLYCEROPENTOPYRANOSID 2 ULOSE |
| 690 | 1 | 0 | |a 2 OCTYL 4 S BENZYL 3 DEOXY 4 THIO BETA DEXTRO GLYCEROPENTOPYRANOSID 2 ULOSE |
| 690 | 1 | 0 | |a 2 OCTYL 4 S BENZYL 3 DEOXY 4 THIO BETA DEXTRO THREO PENTOPYRANOSIDE |
| 690 | 1 | 0 | |a 2 OCTYL 4 S BENZYL 3 DEOXY 4 THIO BETA LEVO GLYCEROPENTOPYRANOSID 2 ULOSE |
| 690 | 1 | 0 | |a 3 DEOXY 4 THIOPENTOPYRANOSID 2 ULOSE |
| 690 | 1 | 0 | |a BENZYL 3 DEOXY 4 S (2 PROPYL) 4 THIO BETA DEXTRO GLYCEROPENTOPYRANOSID 2 ULOSE |
| 690 | 1 | 0 | |a BENZYL 3 DEOXY 4 S ETHYL 4 THIO BETA DEXTRO GLYCEROPENTOPYRANOSID 2 ULOSE |
| 690 | 1 | 0 | |a BENZYL 4 S BENZYL 3 DEOXY 4 THIO BETA DEXTRO GLYCEROPENTOPYRANOSID 2 ULOSE |
| 690 | 1 | 0 | |a CYSTEINE DERIVATIVE |
| 690 | 1 | 0 | |a GLYCOSIDE |
| 690 | 1 | 0 | |a N (TERT BUTOXYCARBONYL)CYSTEINE |
| 690 | 1 | 0 | |a PYRANOSID 2 ULOSE |
| 690 | 1 | 0 | |a PYRANOSIDE |
| 690 | 1 | 0 | |a THIOL DERIVATIVE |
| 690 | 1 | 0 | |a UNCLASSIFIED DRUG |
| 690 | 1 | 0 | |a ARTICLE |
| 690 | 1 | 0 | |a CHEMICAL REACTION |
| 690 | 1 | 0 | |a ENANTIOMER |
| 690 | 1 | 0 | |a ISOMER |
| 690 | 1 | 0 | |a OPTICAL ROTATION |
| 690 | 1 | 0 | |a PRIORITY JOURNAL |
| 690 | 1 | 0 | |a PROTON NUCLEAR MAGNETIC RESONANCE |
| 690 | 1 | 0 | |a REDUCTION |
| 690 | 1 | 0 | |a STEREOCHEMISTRY |
| 690 | 1 | 0 | |a SYNTHESIS |
| 690 | 1 | 0 | |a THIN LAYER CHROMATOGRAPHY |
| 690 | 1 | 0 | |a CARBOHYDRATE CONFORMATION |
| 690 | 1 | 0 | |a GLYCOSIDES |
| 690 | 1 | 0 | |a MAGNETIC RESONANCE SPECTROSCOPY |
| 690 | 1 | 0 | |a PENTOSES |
| 690 | 1 | 0 | |a STEREOISOMERISM |
| 690 | 1 | 0 | |a SULFHYDRYL COMPOUNDS |
| 690 | 1 | 0 | |a THIOGLYCOSIDES |
| 700 | 1 | |a Varela, O. | |
| 773 | 0 | |d 2002 |g v. 337 |h pp. 2069-2076 |k n. 21-23 |p Carbohydr. Res. |x 00086215 |w (AR-BaUEN)CENRE-301 |t Carbohydrate Research | |
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| 856 | 4 | 0 | |u https://doi.org/10.1016/S0008-6215(02)00292-6 |y DOI |
| 856 | 4 | 0 | |u https://hdl.handle.net/20.500.12110/paper_00086215_v337_n21-23_p2069_Uhrig |y Handle |
| 856 | 4 | 0 | |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v337_n21-23_p2069_Uhrig |y Registro en la Biblioteca Digital |
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| 963 | |a VARI | ||
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