Methanesulfonyl chloride → HCID 22803855、化合物

HRID 839579ノート

反応式

HRID 839579 の反応式
[C:1]([S:20][C@@H:21]1[O:29][C@H:28]([CH2:30][OH:31])[C@@H:26]([OH:27])[C@H:24]([OH:25])[C@H:22]1[OH:23])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:32][S:33](Cl)(=[O:35])=[O:34]>N1C=CC=CC=1>[C:1]([S:20][C@@H:21]1[O:29][C@H:28]([CH2:30][O:31][S:33]([CH3:32])(=[O:35])=[O:34])[C@@H:26]([O:27][S:33]([CH3:32])(=[O:35])=[O:34])[C@H:24]([O:25][S:33]([CH3:32])(=[O:35])=[O:34])[C@H:22]1[O:23][S:33]([CH3:32])(=[O:35])=[O:34])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 31297Methanesulfonyl chlorideHCID 54344857HCID 54344857、化合物

生成物 1

HCID 22803855HCID 22803855、化合物

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

S-Trityl-1-thio-β-D-glucopyranose (3.6 g.) was dissolved in 50 ml. dry pyridine, cooled to 0° while 5 ml. (7.5 g.) of methylsulfonyl chloride was added. The solution was placed in the refrigerator for 22 hours until thin layer chromatography showed only traces of starting material or partially reacted products remaining. The solvent was removed at reduced pressure. The oily residue was dissolved in chloroform (200 ml.) and was washed with dilute hydrochloric acid and brine. Evaporating the dried organic extract yielded a product which was chromatographed over a silica dry-column using 20% ethyl acetate-80% chloroform eluant. Pure S-trityl-2,3,4,6-tetra-O-methylsulfonyl-1-thio-β-D-glucopyranose was obtained from ether.

後処理

  1. customThe solvent was removed at reduced pressure
  2. dissolutionThe oily residue was dissolved in chloroform (200 ml.)
  3. washwas washed with dilute hydrochloric acid and brine
  4. customEvaporating the dried
  5. extractionorganic extract
  6. customyielded a product which
  7. customwas chromatographed over a silica dry-column

出典と根拠

ORDレコード
ord-ec2e9a4c661b4a40a9c8db8384cfebd9
出典データセット
uspto-grants-1978_06
特許番号
US04096250

反応ノート

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