(S)-3-Dimethyl-amino-2-{(4S,5R)-5-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl}-2-hydroxy-propanoic acid.
The Kiliani reaction on 1-de-oxy-(N,N-dimethyl-amino)-d-fructose, itself readily available from reaction of dimethyl-amine and d-glucose, proceeded to give access to the title β-sugar amino acid, C(15)H(27)NO(7). X-ray crystallography determined the stereochemistry at the newly formed chiral center....
| Main Authors: | , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
2007
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| _version_ | 1797093061063344128 |
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| author | Jenkinson, S Hotchkiss, D Cowley, A Fleet, G Watkin, D |
| author_facet | Jenkinson, S Hotchkiss, D Cowley, A Fleet, G Watkin, D |
| author_sort | Jenkinson, S |
| collection | OXFORD |
| description | The Kiliani reaction on 1-de-oxy-(N,N-dimethyl-amino)-d-fructose, itself readily available from reaction of dimethyl-amine and d-glucose, proceeded to give access to the title β-sugar amino acid, C(15)H(27)NO(7). X-ray crystallography determined the stereochemistry at the newly formed chiral center. There are two mol-ecules in the asymmetric unit; they are related by a pseudo-twofold rotation axis and have very similar geometries, differing only in the conformation of one of the acetonide rings. All the acetonide rings adopt envelope conformations; the flap atom is oxygen in three of the rings, but carbon in one of them. There are two strong hydrogen bonds between the two independent mol-ecules, and further weak hydrogen bonds link the mol-ecules to form infinite chains running parallel to the a axis. |
| first_indexed | 2024-03-07T03:54:54Z |
| format | Journal article |
| id | oxford-uuid:c2897411-c0fe-4a43-9603-aa4b0b4a778e |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T03:54:54Z |
| publishDate | 2007 |
| record_format | dspace |
| spelling | oxford-uuid:c2897411-c0fe-4a43-9603-aa4b0b4a778e2022-03-27T06:09:43Z(S)-3-Dimethyl-amino-2-{(4S,5R)-5-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl}-2-hydroxy-propanoic acid.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:c2897411-c0fe-4a43-9603-aa4b0b4a778eEnglishSymplectic Elements at Oxford2007Jenkinson, SHotchkiss, DCowley, AFleet, GWatkin, DThe Kiliani reaction on 1-de-oxy-(N,N-dimethyl-amino)-d-fructose, itself readily available from reaction of dimethyl-amine and d-glucose, proceeded to give access to the title β-sugar amino acid, C(15)H(27)NO(7). X-ray crystallography determined the stereochemistry at the newly formed chiral center. There are two mol-ecules in the asymmetric unit; they are related by a pseudo-twofold rotation axis and have very similar geometries, differing only in the conformation of one of the acetonide rings. All the acetonide rings adopt envelope conformations; the flap atom is oxygen in three of the rings, but carbon in one of them. There are two strong hydrogen bonds between the two independent mol-ecules, and further weak hydrogen bonds link the mol-ecules to form infinite chains running parallel to the a axis. |
| spellingShingle | Jenkinson, S Hotchkiss, D Cowley, A Fleet, G Watkin, D (S)-3-Dimethyl-amino-2-{(4S,5R)-5-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl}-2-hydroxy-propanoic acid. |
| title | (S)-3-Dimethyl-amino-2-{(4S,5R)-5-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl}-2-hydroxy-propanoic acid. |
| title_full | (S)-3-Dimethyl-amino-2-{(4S,5R)-5-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl}-2-hydroxy-propanoic acid. |
| title_fullStr | (S)-3-Dimethyl-amino-2-{(4S,5R)-5-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl}-2-hydroxy-propanoic acid. |
| title_full_unstemmed | (S)-3-Dimethyl-amino-2-{(4S,5R)-5-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl}-2-hydroxy-propanoic acid. |
| title_short | (S)-3-Dimethyl-amino-2-{(4S,5R)-5-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl}-2-hydroxy-propanoic acid. |
| title_sort | s 3 dimethyl amino 2 4s 5r 5 r 2 2 dimethyl 1 3 dioxolan 4 yl 2 2 dimethyl 1 3 dioxolan 4 yl 2 hydroxy propanoic acid |
| work_keys_str_mv | AT jenkinsons s3dimethylamino24s5r5r22dimethyl13dioxolan4yl22dimethyl13dioxolan4yl2hydroxypropanoicacid AT hotchkissd s3dimethylamino24s5r5r22dimethyl13dioxolan4yl22dimethyl13dioxolan4yl2hydroxypropanoicacid AT cowleya s3dimethylamino24s5r5r22dimethyl13dioxolan4yl22dimethyl13dioxolan4yl2hydroxypropanoicacid AT fleetg s3dimethylamino24s5r5r22dimethyl13dioxolan4yl22dimethyl13dioxolan4yl2hydroxypropanoicacid AT watkind s3dimethylamino24s5r5r22dimethyl13dioxolan4yl22dimethyl13dioxolan4yl2hydroxypropanoicacid |