Pyridine → 1,4-Anhydro-2-deoxy-D-erythro-pentitol 5-(Trifluoromethanesulfonate)

HRID 1450337노트

반응식

HRID 1450337 반응식
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[CH2:16]1[O:21][C@H:20]([CH2:22]O)[C@@H:18]([OH:19])[CH2:17]1.N1C=CC=CC=1>C(Cl)Cl>[F:1][C:2]([F:15])([F:14])[S:3]([O:6][CH2:22][C@H:20]1[O:21][CH2:16][CH2:17][C@@H:18]1[OH:19])(=[O:5])=[O:4]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 1246571,2-Dideoxyribofuranose

생성물 1

HCID 867503491,4-Anhydro-2-deoxy-D-erythro-pentitol 5-(Trifluoromethanesulfonate)

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a -20° C. solution, under argon, of 8.4 ml of trifluoromethanesulfonic anhydride in 75 ml of methylene chloride is added, dropwise, a solution of 5.9 g of product from Example 268 and 4.05 ml of pyridine in 25 ml of methylene chloride. The temperature is maintained below -10° C. during the addition. The progress of the reaction is monitored by tlc. The reaction is filtered and the filtrate concentrated in vacuo to an oily residue. The residue is purified by chromatography (silica gel: 50% ethyl acetate/hexane) to give 7.03 g of the desired product.

후처리

  1. temperatureThe temperature is maintained below -10° C. during the addition
  2. filtrationThe reaction is filtered
  3. concentrationthe filtrate concentrated in vacuo to an oily residue
  4. customThe residue is purified by chromatography (silica gel: 50% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-890234f035e144d3ac5dece436c799e4
출처 데이터셋
uspto-grants-1997_02
특허 번호
US05602118

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