Asymmetric syntheses of methyl N-Boc-2-deoxy-2-amino-L-erythroside, methyl N-Boc-2-deoxy-2-amino-D-threoside and methyl N-Boc-2,3-dideoxy-3-amino-L-arabinopyranoside
The asymmetric syntheses of methyl N-Boc-2-deoxy-2-amino-l-erythroside and methyl N-Boc-2-deoxy-2-amino-d-threoside have been achieved from sorbic acid, in six and eight steps, and in 35 and 13% overall yield, respectively. Diastereoselective aminohydroxylation of tert-butyl sorbate gives access to...
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| Fformat: | Journal article |
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2014
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| _version_ | 1826296783005810688 |
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| author | Brambilla, M Davies, S Fletcher, A Hao, L Lv, L Roberts, P Thomson, J |
| author_facet | Brambilla, M Davies, S Fletcher, A Hao, L Lv, L Roberts, P Thomson, J |
| author_sort | Brambilla, M |
| collection | OXFORD |
| description | The asymmetric syntheses of methyl N-Boc-2-deoxy-2-amino-l-erythroside and methyl N-Boc-2-deoxy-2-amino-d-threoside have been achieved from sorbic acid, in six and eight steps, and in 35 and 13% overall yield, respectively. Diastereoselective aminohydroxylation of tert-butyl sorbate gives access to two diastereoisomeric α-hydroxy-β-amino-γ,δ-unsaturated esters. Reduction of the ester functionality and ozonolysis of the double bond gives the corresponding aldehyde, which exists exclusively in the ring-closed (furanose) form. An alternative synthesis of methyl N-Boc-2-deoxy-2-amino-l-erythroside was also developed, reliant on aminohydroxylation of an α,β-unsaturated ester bearing an acetal functionality at the γ-position, and this synthesis proceeded in five steps and 54% overall yield from acrolein diethyl acetal. This approach was extended to permit the synthesis of methyl N-Boc-2,3-dideoxy-3-amino-l-arabinopyranoside in six steps and 58% overall yield from ethyl 3,3-diethoxypropanote. © 2014 Elsevier Ltd. All rights reserved. |
| first_indexed | 2024-03-07T04:21:39Z |
| format | Journal article |
| id | oxford-uuid:cb3867a5-d697-4429-84ea-c4766a3bf7eb |
| institution | University of Oxford |
| last_indexed | 2024-03-07T04:21:39Z |
| publishDate | 2014 |
| record_format | dspace |
| spelling | oxford-uuid:cb3867a5-d697-4429-84ea-c4766a3bf7eb2022-03-27T07:13:19ZAsymmetric syntheses of methyl N-Boc-2-deoxy-2-amino-L-erythroside, methyl N-Boc-2-deoxy-2-amino-D-threoside and methyl N-Boc-2,3-dideoxy-3-amino-L-arabinopyranosideJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:cb3867a5-d697-4429-84ea-c4766a3bf7ebSymplectic Elements at Oxford2014Brambilla, MDavies, SFletcher, AHao, LLv, LRoberts, PThomson, JThe asymmetric syntheses of methyl N-Boc-2-deoxy-2-amino-l-erythroside and methyl N-Boc-2-deoxy-2-amino-d-threoside have been achieved from sorbic acid, in six and eight steps, and in 35 and 13% overall yield, respectively. Diastereoselective aminohydroxylation of tert-butyl sorbate gives access to two diastereoisomeric α-hydroxy-β-amino-γ,δ-unsaturated esters. Reduction of the ester functionality and ozonolysis of the double bond gives the corresponding aldehyde, which exists exclusively in the ring-closed (furanose) form. An alternative synthesis of methyl N-Boc-2-deoxy-2-amino-l-erythroside was also developed, reliant on aminohydroxylation of an α,β-unsaturated ester bearing an acetal functionality at the γ-position, and this synthesis proceeded in five steps and 54% overall yield from acrolein diethyl acetal. This approach was extended to permit the synthesis of methyl N-Boc-2,3-dideoxy-3-amino-l-arabinopyranoside in six steps and 58% overall yield from ethyl 3,3-diethoxypropanote. © 2014 Elsevier Ltd. All rights reserved. |
| spellingShingle | Brambilla, M Davies, S Fletcher, A Hao, L Lv, L Roberts, P Thomson, J Asymmetric syntheses of methyl N-Boc-2-deoxy-2-amino-L-erythroside, methyl N-Boc-2-deoxy-2-amino-D-threoside and methyl N-Boc-2,3-dideoxy-3-amino-L-arabinopyranoside |
| title | Asymmetric syntheses of methyl N-Boc-2-deoxy-2-amino-L-erythroside, methyl N-Boc-2-deoxy-2-amino-D-threoside and methyl N-Boc-2,3-dideoxy-3-amino-L-arabinopyranoside |
| title_full | Asymmetric syntheses of methyl N-Boc-2-deoxy-2-amino-L-erythroside, methyl N-Boc-2-deoxy-2-amino-D-threoside and methyl N-Boc-2,3-dideoxy-3-amino-L-arabinopyranoside |
| title_fullStr | Asymmetric syntheses of methyl N-Boc-2-deoxy-2-amino-L-erythroside, methyl N-Boc-2-deoxy-2-amino-D-threoside and methyl N-Boc-2,3-dideoxy-3-amino-L-arabinopyranoside |
| title_full_unstemmed | Asymmetric syntheses of methyl N-Boc-2-deoxy-2-amino-L-erythroside, methyl N-Boc-2-deoxy-2-amino-D-threoside and methyl N-Boc-2,3-dideoxy-3-amino-L-arabinopyranoside |
| title_short | Asymmetric syntheses of methyl N-Boc-2-deoxy-2-amino-L-erythroside, methyl N-Boc-2-deoxy-2-amino-D-threoside and methyl N-Boc-2,3-dideoxy-3-amino-L-arabinopyranoside |
| title_sort | asymmetric syntheses of methyl n boc 2 deoxy 2 amino l erythroside methyl n boc 2 deoxy 2 amino d threoside and methyl n boc 2 3 dideoxy 3 amino l arabinopyranoside |
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