Doubly carbon-branched pentoses: synthesis of both enantiomers of 2.4-di-C-methyl arabinose and 2-deoxy-2,4-di-C-methyl arabinose using only acetonide protection

An acetonide is the only protecting group used in the synthesis of both the enantiomers of 2,4-di-C-methyl arabinose and 2-deoxy-2,4-di-C-methyl arabinose via the enantiomeric 3-C-methyl-l-erythronolactone [from 2-C-methyl-d-ribono-lactone or d-ribose] and 3-C-methyl-d-erythronolactone [from d-tagat...

Mô tả đầy đủ

Chi tiết về thư mục
Những tác giả chính: Booth, K, Jenkinson, S, Best, D, Fernandez Nieto, F, Estevez, R, Wormald, M, Weymouth-Wilson, A, Fleet, G
Định dạng: Journal article
Ngôn ngữ:English
Được phát hành: 2009
_version_ 1826272427214110720
author Booth, K
Jenkinson, S
Best, D
Fernandez Nieto, F
Estevez, R
Wormald, M
Weymouth-Wilson, A
Fleet, G
author_facet Booth, K
Jenkinson, S
Best, D
Fernandez Nieto, F
Estevez, R
Wormald, M
Weymouth-Wilson, A
Fleet, G
author_sort Booth, K
collection OXFORD
description An acetonide is the only protecting group used in the synthesis of both the enantiomers of 2,4-di-C-methyl arabinose and 2-deoxy-2,4-di-C-methyl arabinose via the enantiomeric 3-C-methyl-l-erythronolactone [from 2-C-methyl-d-ribono-lactone or d-ribose] and 3-C-methyl-d-erythronolactone [from d-tagatose or l-ribose]. NMR studies on unprotected C-methyl arabinoses show that methyl branching significantly affects the ratios of pyranose and furanose forms present in aqueous solution. © 2009 Elsevier Ltd. All rights reserved.
first_indexed 2024-03-06T22:12:24Z
format Journal article
id oxford-uuid:52446a12-49b0-41d2-84e7-0dde82ca79b9
institution University of Oxford
language English
last_indexed 2024-03-06T22:12:24Z
publishDate 2009
record_format dspace
spelling oxford-uuid:52446a12-49b0-41d2-84e7-0dde82ca79b92022-03-26T16:24:32ZDoubly carbon-branched pentoses: synthesis of both enantiomers of 2.4-di-C-methyl arabinose and 2-deoxy-2,4-di-C-methyl arabinose using only acetonide protectionJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:52446a12-49b0-41d2-84e7-0dde82ca79b9EnglishSymplectic Elements at Oxford2009Booth, KJenkinson, SBest, DFernandez Nieto, FEstevez, RWormald, MWeymouth-Wilson, AFleet, GAn acetonide is the only protecting group used in the synthesis of both the enantiomers of 2,4-di-C-methyl arabinose and 2-deoxy-2,4-di-C-methyl arabinose via the enantiomeric 3-C-methyl-l-erythronolactone [from 2-C-methyl-d-ribono-lactone or d-ribose] and 3-C-methyl-d-erythronolactone [from d-tagatose or l-ribose]. NMR studies on unprotected C-methyl arabinoses show that methyl branching significantly affects the ratios of pyranose and furanose forms present in aqueous solution. © 2009 Elsevier Ltd. All rights reserved.
spellingShingle Booth, K
Jenkinson, S
Best, D
Fernandez Nieto, F
Estevez, R
Wormald, M
Weymouth-Wilson, A
Fleet, G
Doubly carbon-branched pentoses: synthesis of both enantiomers of 2.4-di-C-methyl arabinose and 2-deoxy-2,4-di-C-methyl arabinose using only acetonide protection
title Doubly carbon-branched pentoses: synthesis of both enantiomers of 2.4-di-C-methyl arabinose and 2-deoxy-2,4-di-C-methyl arabinose using only acetonide protection
title_full Doubly carbon-branched pentoses: synthesis of both enantiomers of 2.4-di-C-methyl arabinose and 2-deoxy-2,4-di-C-methyl arabinose using only acetonide protection
title_fullStr Doubly carbon-branched pentoses: synthesis of both enantiomers of 2.4-di-C-methyl arabinose and 2-deoxy-2,4-di-C-methyl arabinose using only acetonide protection
title_full_unstemmed Doubly carbon-branched pentoses: synthesis of both enantiomers of 2.4-di-C-methyl arabinose and 2-deoxy-2,4-di-C-methyl arabinose using only acetonide protection
title_short Doubly carbon-branched pentoses: synthesis of both enantiomers of 2.4-di-C-methyl arabinose and 2-deoxy-2,4-di-C-methyl arabinose using only acetonide protection
title_sort doubly carbon branched pentoses synthesis of both enantiomers of 2 4 di c methyl arabinose and 2 deoxy 2 4 di c methyl arabinose using only acetonide protection
work_keys_str_mv AT boothk doublycarbonbranchedpentosessynthesisofbothenantiomersof24dicmethylarabinoseand2deoxy24dicmethylarabinoseusingonlyacetonideprotection
AT jenkinsons doublycarbonbranchedpentosessynthesisofbothenantiomersof24dicmethylarabinoseand2deoxy24dicmethylarabinoseusingonlyacetonideprotection
AT bestd doublycarbonbranchedpentosessynthesisofbothenantiomersof24dicmethylarabinoseand2deoxy24dicmethylarabinoseusingonlyacetonideprotection
AT fernandeznietof doublycarbonbranchedpentosessynthesisofbothenantiomersof24dicmethylarabinoseand2deoxy24dicmethylarabinoseusingonlyacetonideprotection
AT estevezr doublycarbonbranchedpentosessynthesisofbothenantiomersof24dicmethylarabinoseand2deoxy24dicmethylarabinoseusingonlyacetonideprotection
AT wormaldm doublycarbonbranchedpentosessynthesisofbothenantiomersof24dicmethylarabinoseand2deoxy24dicmethylarabinoseusingonlyacetonideprotection
AT weymouthwilsona doublycarbonbranchedpentosessynthesisofbothenantiomersof24dicmethylarabinoseand2deoxy24dicmethylarabinoseusingonlyacetonideprotection
AT fleetg doublycarbonbranchedpentosessynthesisofbothenantiomersof24dicmethylarabinoseand2deoxy24dicmethylarabinoseusingonlyacetonideprotection