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

HRID 1944789

반응식

HRID 1944789 반응식
[O:1]=[CH:2][C@H:3]([C@H:5]([C@H:7]([CH2:9][OH:10])[OH:8])[OH:6])[OH:4].Cl.C(O[C:16](=[O:18])[CH3:17])(=O)C.S(=O)(=O)(O)O.[C:24]([OH:27])(=O)[CH3:25]>CO.N1C=CC=CC=1>[C:2]([O:1][C@H:2]1[O:8][C@@H:7]([CH2:9][O:10][C:16](=[O:18])[CH3:17])[C@H:5]([O:6][C:24](=[O:27])[CH3:25])[C@@H:3]1[O:4][C:5](=[O:6])[CH3:7])(=[O:1])[CH3:3]

참가 물질

8

반응물 5

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 7918Acetic Anhydride2회HCID 90428L-Ribose

생성물 1

HCID 908100(2R,3S,4S,5S)-5-(acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate수율 57%

시약·촉매·용매 2

HCID 887Methanol용매HCID 1049Pyridine용매

실험 절차

In Non-Patent Document 2, L-ribose is used as a starting material, the alkylation of the hydroxyl group at 1-position is carried out in methanol that contains hydrochloric acid, the acetylation is carried out with acetic anhydride in pyridine, and the acetolysis is carried out in acetic acid and acetic anhydride in the presence of concentrated sulfuric acid. By recrystallizing from ethyl ether, 1,2,3,5-tetra-O-acetyl-β-L-ribofuranose is obtained at a total yield of 57%. Hereinafter, in the present specification, 1,2,3,5-tetra-O-acetyl-β-L-ribofuranose may be referred to as β-L-TAR at times, and 1,2,3,5-tetra-O-acetyl-L-ribofuranose may be referred to as L-TAR at times.

후처리

  1. customBy recrystallizing from ethyl ether

출처 및 근거

ORD 기록
ord-77c4ed05c16c4c359fd204d04d4c9fac
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394935B2

연결된 노트

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