Sulfuric Acid → (2R,3S,4S,5S)-5-(acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate

HRID 1944790

反応式

HRID 1944790 の反応式
O=C[C@H]([C@H]([C@H](CO)O)O)O.S(=O)(=O)(O)O.C(=O)([O-])[O-].[Li+].[Li+].[C:22]([O:25][CH:26]1[O:38][C@@H:37]([CH2:39][O:40][C:41](=[O:43])[CH3:42])[C@H:32]([O:33][C:34](=[O:36])[CH3:35])[C@@H:27]1[O:28][C:29](=[O:31])[CH3:30])(=[O:24])[CH3:23]>CO.C(O)(=O)C.C(OC(=O)C)(=O)C.C(O)(C)C.O>[C:22]([O:25][C@H:26]1[O:38][C@@H:37]([CH2:39][O:40][C:41](=[O:43])[CH3:42])[C@H:32]([O:33][C:34](=[O:36])[CH3:35])[C@@H:27]1[O:28][C:29](=[O:31])[CH3:30])(=[O:24])[CH3:23]

参加物

10

反応物 4

HCID 1118Sulfuric Acid2 回HCID 11125Lithium CarbonateHCID 90428L-RiboseHCID 114934341,2,3,5-tetra-O-acetyl-L-ribofuranose

生成物 1

HCID 908100(2R,3S,4S,5S)-5-(acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate収率 60%

試薬・触媒・溶媒 5

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒HCID 962Water溶媒HCID 3776Isopropanol溶媒HCID 7918Acetic Anhydride溶媒2 回

実験手順

In Non-Patent Document 6, L-ribose is used as a starting material, the methylation of the hydroxyl group at 1-position is carried out in methanol in the presence of sulfuric acid, the resultant mixture is then treated with lithium carbonate, the acetylation is then carried out in acetic acid and acetic anhydride, and concentrated sulfuric acid and acetic anhydride are further added thereto to carry out the acetolysis. A crude product is a mixture of α/β-anomers of 1,2,3,5-tetra-O-acetyl-L-ribofuranose. The crude product is treated with water and isopropyl alcohol to obtain 1,2,3,5-tetra-O-acetyl-β-L-ribofuranose at a total yield of 60%.

出典と根拠

ORDレコード
ord-9025124fd92c45129b3beb332837a7c3
出典データセット
uspto-grants-2013_03
特許番号
US08394935B2

関連ノート

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