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

HRID 1450337ノート

反応式

HRID 1450337 の反応式
[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]

参加物

5

反応物 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 1246571,2-Dideoxyribofuranose

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-890234f035e144d3ac5dece436c799e4
出典データセット
uspto-grants-1997_02
特許番号
US05602118

反応ノート

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