Carbon-branched carbohydrate chirons: practical access to both enantiomers of 2-C-methyl-ribono-1,4-lactone and 2-C-methyl-arabinonolactone

Readily crystallized 2-C-methyl-d-ribono-1,4-lactone is formed in a one-pot procedure from d-glucose without any protecting groups by treatment with dimethylamine to give an Amadori ketose and then with aqueous calcium hydroxide in yields of approximately 25%; 2-C-methyl-l-ribono-1,4-lactone is simi...

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Автори: Booth, K, da Cruz, F, Hotchkiss, D, Jenkinson, S, Jones, N, Weymouth-Wilson, A, Clarkson, R, Heinz, T, Fleet, G
Формат: Journal article
Мова:English
Опубліковано: 2008
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author Booth, K
da Cruz, F
Hotchkiss, D
Jenkinson, S
Jones, N
Weymouth-Wilson, A
Clarkson, R
Heinz, T
Fleet, G
author_facet Booth, K
da Cruz, F
Hotchkiss, D
Jenkinson, S
Jones, N
Weymouth-Wilson, A
Clarkson, R
Heinz, T
Fleet, G
author_sort Booth, K
collection OXFORD
description Readily crystallized 2-C-methyl-d-ribono-1,4-lactone is formed in a one-pot procedure from d-glucose without any protecting groups by treatment with dimethylamine to give an Amadori ketose and then with aqueous calcium hydroxide in yields of approximately 25%; 2-C-methyl-l-ribono-1,4-lactone is similarly produced from l-glucose. 3,4-O-Isopropylidene-2-C-methyl-d-arabinono-1,5-lactone and 2-C-methyl-d-arabinono-1,4-lactone were prepared in a combined 60% yield by the Kiliani reaction of sodium cyanide with a protected 1-deoxy-d-ribulose derived from d-erythronolactone; the enantiomeric arabinonolactones are similarly available from l-erythronolactone. © 2008 Elsevier Ltd. All rights reserved.
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spelling oxford-uuid:9a3c3d1c-d54e-4e2e-aea5-5cbe5f7eff452022-03-27T00:19:53ZCarbon-branched carbohydrate chirons: practical access to both enantiomers of 2-C-methyl-ribono-1,4-lactone and 2-C-methyl-arabinonolactoneJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:9a3c3d1c-d54e-4e2e-aea5-5cbe5f7eff45EnglishSymplectic Elements at Oxford2008Booth, Kda Cruz, FHotchkiss, DJenkinson, SJones, NWeymouth-Wilson, AClarkson, RHeinz, TFleet, GReadily crystallized 2-C-methyl-d-ribono-1,4-lactone is formed in a one-pot procedure from d-glucose without any protecting groups by treatment with dimethylamine to give an Amadori ketose and then with aqueous calcium hydroxide in yields of approximately 25%; 2-C-methyl-l-ribono-1,4-lactone is similarly produced from l-glucose. 3,4-O-Isopropylidene-2-C-methyl-d-arabinono-1,5-lactone and 2-C-methyl-d-arabinono-1,4-lactone were prepared in a combined 60% yield by the Kiliani reaction of sodium cyanide with a protected 1-deoxy-d-ribulose derived from d-erythronolactone; the enantiomeric arabinonolactones are similarly available from l-erythronolactone. © 2008 Elsevier Ltd. All rights reserved.
spellingShingle Booth, K
da Cruz, F
Hotchkiss, D
Jenkinson, S
Jones, N
Weymouth-Wilson, A
Clarkson, R
Heinz, T
Fleet, G
Carbon-branched carbohydrate chirons: practical access to both enantiomers of 2-C-methyl-ribono-1,4-lactone and 2-C-methyl-arabinonolactone
title Carbon-branched carbohydrate chirons: practical access to both enantiomers of 2-C-methyl-ribono-1,4-lactone and 2-C-methyl-arabinonolactone
title_full Carbon-branched carbohydrate chirons: practical access to both enantiomers of 2-C-methyl-ribono-1,4-lactone and 2-C-methyl-arabinonolactone
title_fullStr Carbon-branched carbohydrate chirons: practical access to both enantiomers of 2-C-methyl-ribono-1,4-lactone and 2-C-methyl-arabinonolactone
title_full_unstemmed Carbon-branched carbohydrate chirons: practical access to both enantiomers of 2-C-methyl-ribono-1,4-lactone and 2-C-methyl-arabinonolactone
title_short Carbon-branched carbohydrate chirons: practical access to both enantiomers of 2-C-methyl-ribono-1,4-lactone and 2-C-methyl-arabinonolactone
title_sort carbon branched carbohydrate chirons practical access to both enantiomers of 2 c methyl ribono 1 4 lactone and 2 c methyl arabinonolactone
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