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

HRID 1944790

반응식

HRID 1944790 반응식
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]

참가 물질

10

반응물 4

HCID 1118Sulfuric Acid2회HCID 11125Lithium CarbonateHCID 90428L-RiboseHCID 114934341,2,3,5-tetra-O-acetyl-L-ribofuranose

생성물 1

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

시약·촉매·용매 5

HCID 176Acetic Acid용매HCID 887Methanol용매HCID 962Water용매HCID 3776Isopropanol용매HCID 7918Acetic Anhydride용매2회

실험 절차

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%.

출처 및 근거

ORD 기록
ord-9025124fd92c45129b3beb332837a7c3
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394935B2

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