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Methanol → HCID 88089139、化合物

HRID 2380189
ノート
印刷プレビュー

反応式

HRID 2380189 の反応式
[CH2:1]([SH:3])[CH3:2].C[OH:5].CC1C=CC(S([O:16][CH2:17][C@H:18]2[O:22][C@@H:21](OC)[C@@H:20]3OC(C)(C)O[C@H:19]23)(=O)=O)=CC=1>C[O-].[Na+]>[CH2:20]([CH2:19][C@@H:18]([OH:22])[C@@H:17]([OH:16])[C@@H:2]([OH:5])[CH:1]=[S:3])[CH3:21]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 887MethanolHCID 6343EthanethiolHCID 11013769beta-D-Ribofuranoside, methyl 2,3-O-(1-methylethylidene)-, 5-(4-methylbenzenesulfonate)

生成物 1

HCID 88089139HCID 88089139、化合物収率 120.2%

試薬・触媒・溶媒 1

HCID 10942334Sodium Methoxide溶媒

実験手順

A solution of ethanethiol (11.5 ml, 155 mmol) in 1N sodium methoxide in methanol (150 ml, 150 mmol sodium methoxide) was added to a solution of methyl 2,3-O-isopropylidene-5-O-p-toluenesulfonyl-β-D-ribofuranoside (50 g, 140 mmol in 200 ml dry methanol) and heated at reflux for 24 h. Solvents were removed by evaporation in vacuo, and the sticky residue was taken up in diethyl ether (300 ml) and washed with water (4×100 ml). The ether phase was dried and concentrated in vacuo to furnish a viscous oil. Fractional distillation (70° C. at 0.06 Torr) using a short-path distillation apparatus afforded 30.0 g (86.5% yield) of methyl 5-deoxy-5-ethylthio2,3-O-isopropylidene-β-D-ribofuranoside (III) as a colorless, viscous oil. TLC (silica; 25% ethylacetate in hexane): Rf 0.44 (III); visualization spray as in A above.

後処理

  1. temperatureheated
  2. temperatureat reflux for 24 h
  3. customSolvents were removed by evaporation in vacuo
  4. washwashed with water (4×100 ml)
  5. dry with materialThe ether phase was dried
  6. concentrationconcentrated in vacuo
  7. customto furnish a viscous oil
  8. distillationFractional distillation (70° C. at 0.06 Torr)

出典と根拠

ORDレコード
ord-29e1fcd2151145ff82e007c3d9dcbf7c
出典データセット
uspto-grants-1994_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05366954

反応ノート

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