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Article: Stereoselective epoxidation of divinylmethanol: A synthetic approach to the pentitols
Title | Stereoselective epoxidation of divinylmethanol: A synthetic approach to the pentitols |
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Authors | |
Issue Date | 1982 |
Citation | Carbohydrate Research, 1982, v. 100, n. 1, p. 207-220 How to Cite? |
Abstract | Peroxy-acid epoxidation of divinylmethanol (9), followed by acetylation afforded the acetylated monoepoxides 1 and 2 having the erythro (53%) and threo (47%) configurations. Peroxy-acid epoxidation of 1 and 2 yielded the acetylated diepoxides 3 (erythro-erythro, 36%) and 4 (erythro-threo, 64%) (from 1), and 4 (erythro-threo, 47%) and 5 (threo-threo, 53%) (from 2). Relative configurational assignments were made to 1-5 on the basis of (a) 1H-n.m.r. chemical-shift and coupling-constant data, (b) the observation that 1 gave only 3 and 4, and that 2 gave only 4 and 5 on epoxidation, and (c) the fact that 3-5 separately undergo epoxide-ring opening preferentially at their primary carbon atoms with acetate ion in acetic anhydride, to afford the penta-acetates of ribitol, dl-arabinitol, and xylitol, respectively, as major products. Epoxide-ring formation favours the erythro configuration when either peroxy acids or tert-butyl hydroperoxide with catalytically active Ti4+, V5+, or Mo6+ complexes are employed as epoxidation reagents. However, the diastereoselectivities characterising the epoxidations and the regioselectivities governing the epoxide-ring openings are not sufficiently high to constitute an attractive synthesis of either ribitol, dl-arabinitol, or xylitol from divinylmethanol. {A figure is presented}. © 1982. |
Persistent Identifier | http://hdl.handle.net/10722/332550 |
ISSN | 2023 Impact Factor: 2.4 2023 SCImago Journal Rankings: 0.509 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Holland, David | - |
dc.contributor.author | Fraser Stoddart, J. | - |
dc.date.accessioned | 2023-10-06T05:12:23Z | - |
dc.date.available | 2023-10-06T05:12:23Z | - |
dc.date.issued | 1982 | - |
dc.identifier.citation | Carbohydrate Research, 1982, v. 100, n. 1, p. 207-220 | - |
dc.identifier.issn | 0008-6215 | - |
dc.identifier.uri | http://hdl.handle.net/10722/332550 | - |
dc.description.abstract | Peroxy-acid epoxidation of divinylmethanol (9), followed by acetylation afforded the acetylated monoepoxides 1 and 2 having the erythro (53%) and threo (47%) configurations. Peroxy-acid epoxidation of 1 and 2 yielded the acetylated diepoxides 3 (erythro-erythro, 36%) and 4 (erythro-threo, 64%) (from 1), and 4 (erythro-threo, 47%) and 5 (threo-threo, 53%) (from 2). Relative configurational assignments were made to 1-5 on the basis of (a) 1H-n.m.r. chemical-shift and coupling-constant data, (b) the observation that 1 gave only 3 and 4, and that 2 gave only 4 and 5 on epoxidation, and (c) the fact that 3-5 separately undergo epoxide-ring opening preferentially at their primary carbon atoms with acetate ion in acetic anhydride, to afford the penta-acetates of ribitol, dl-arabinitol, and xylitol, respectively, as major products. Epoxide-ring formation favours the erythro configuration when either peroxy acids or tert-butyl hydroperoxide with catalytically active Ti4+, V5+, or Mo6+ complexes are employed as epoxidation reagents. However, the diastereoselectivities characterising the epoxidations and the regioselectivities governing the epoxide-ring openings are not sufficiently high to constitute an attractive synthesis of either ribitol, dl-arabinitol, or xylitol from divinylmethanol. {A figure is presented}. © 1982. | - |
dc.language | eng | - |
dc.relation.ispartof | Carbohydrate Research | - |
dc.title | Stereoselective epoxidation of divinylmethanol: A synthetic approach to the pentitols | - |
dc.type | Article | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1016/S0008-6215(00)81036-8 | - |
dc.identifier.scopus | eid_2-s2.0-0343529843 | - |
dc.identifier.volume | 100 | - |
dc.identifier.issue | 1 | - |
dc.identifier.spage | 207 | - |
dc.identifier.epage | 220 | - |
dc.identifier.isi | WOS:A1982NL13700016 | - |