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Abstract:

(Chemical Equation Presented) 3,4-Anhydro hexopyranosides have been prepared by diastereoselective epoxidation of derivatives of 2-propyl 3,4-dideoxy-α-D-erythro-hex-3-enopyranoside (5), selectively protected at HO-2 and HO-6. The allylic group at C-2, in 5 and derivatives, plays a critical role in the facial selectivity of the epoxidation reaction. Thus, the free HO-2 in 3 (the 6-O-acetyl derivative of 5) directs the attack of m-chloroperbenzoic acid from the more hindered α face of the molecule to give 2-propyl 6-O-acetyl-3,4-anhydro-α-D-allopyranoside (7) accompanied by the β epoxide 6 as a very minor product. Reverse diastereoselectivity has been obtained when the HO-2 in 3 was substituted by a bulky tert-butyldimethylsilyl (TBS) group. In this case, the major isomer was the 2-O-TBS derivative of 6 (α-D-galacto configuration). The ring-opening of sugar epoxides by nucleophilic per-O-acetyl-1-thio-β-D-glucopyranose (11) was employed as a convenient approach to the synthesis of (1→3)-and (1→4)- thiodisaccharides. For example, ring-opening of the oxirane 7 by 11 led to the expected regioisomeric per-O-acetyl thiodisaccharides β-D-Glc-S-(1→3)- 4-thio-α-D-Glc-O-iPr (12) and β-D-Glc-S-(1→4)4-thio-α-D- Gul-O-iPr (13). Regioselectivity in the construction of the (1→4)- thioglycosidic linkage could be achieved by hindering C-3 of the 3,4-anhydro sugar with a bulky silyloxy group at the vicinal C-2. For instance, coupling of the 2-O-TBS derivative of 7 with 11 led regioselectively to the protected thiodisaccharide β-D-Glc-S-(1→4)-4-thio-α-D-Glc-O-iPr (27). The utility of the approach was demonstrated through the synthesis of sulfur-linked analogues of naturally occurring (laminarabiose and cellobiose) and non-natural disaccharides (i.e., β-D-Glc-(1→4)-α-D-Gul). © 2008 American Chemical Society.

Registro:

Documento: Artículo
Título:Straightforward synthesis of thiodisaccharides by ring-opening of sugar epoxides
Autor:Manzano, V.E.; Uhrig, M.L.; Varela, O.
Filiación:CIHIDECAR-CONICET, Departamento de Química Orgánica, Universidad de Buenos Aires, Argentina
Palabras clave:Chemical reactions; Derivatives; Epoxidation; Polysaccharides; Silicones; Sugar (sucrose); Sulfur; Synthesis (chemical); Cellobiose; Chemical equations; D-glucopyranose; Diastereo-selectivity; Diastereoselective epoxidation; Erythro; Facial selectivity; Laminarabiose; M-chloroperbenzoic acid; Oxirane; Ring-opening; Tert-butyldimethylsilyl; Thiodisaccharide; Sugars; 2 propyl 3,4 dideoxy alpha dextro erythrohex 3 enopyranoside; 2 propyl 6 o acetyl 3,4 anhydro alpha dextro allopyranoside; 3 chloroperbenzoic acid; allyl compound; cellobiose; disaccharide; epoxide; ethylene oxide derivative; per o acetyl 1 thio beta dextro glucopyranose; peracetic acid; pyranoside; silane derivative; sugar; sulfur derivative; tert butyldimethylsilyl; thiol; unclassified drug; acetylation; article; chemical bond; chemical structure; diastereoisomer; epoxidation; proton nuclear magnetic resonance; reaction analysis; ring opening; synthesis; Carbohydrate Conformation; Carbohydrates; Disaccharides; Epoxy Compounds; Stereoisomerism
Año:2008
Volumen:73
Número:18
Página de inicio:7224
Página de fin:7235
DOI: http://dx.doi.org/10.1021/jo8012397
Título revista:Journal of Organic Chemistry
Título revista abreviado:J. Org. Chem.
ISSN:00223263
CODEN:JOCEA
CAS:3 chloroperbenzoic acid, 937-14-4; cellobiose, 16462-44-5, 528-50-7; peracetic acid, 79-21-0, 8065-77-8; Carbohydrates; Disaccharides; Epoxy Compounds
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223263_v73_n18_p7224_Manzano

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Citas:

---------- APA ----------
Manzano, V.E., Uhrig, M.L. & Varela, O. (2008) . Straightforward synthesis of thiodisaccharides by ring-opening of sugar epoxides. Journal of Organic Chemistry, 73(18), 7224-7235.
http://dx.doi.org/10.1021/jo8012397
---------- CHICAGO ----------
Manzano, V.E., Uhrig, M.L., Varela, O. "Straightforward synthesis of thiodisaccharides by ring-opening of sugar epoxides" . Journal of Organic Chemistry 73, no. 18 (2008) : 7224-7235.
http://dx.doi.org/10.1021/jo8012397
---------- MLA ----------
Manzano, V.E., Uhrig, M.L., Varela, O. "Straightforward synthesis of thiodisaccharides by ring-opening of sugar epoxides" . Journal of Organic Chemistry, vol. 73, no. 18, 2008, pp. 7224-7235.
http://dx.doi.org/10.1021/jo8012397
---------- VANCOUVER ----------
Manzano, V.E., Uhrig, M.L., Varela, O. Straightforward synthesis of thiodisaccharides by ring-opening of sugar epoxides. J. Org. Chem. 2008;73(18):7224-7235.
http://dx.doi.org/10.1021/jo8012397