Methanol → Methyl 2-deoxy-5-O-(triphenylmethyl)-D-erythro-pentofuranoside

HRID 1199117ノート

反応式

HRID 1199117 の反応式
[O:1]([CH3:10])[CH:2]1[O:7][C@H:6]([CH2:8][OH:9])[C@@H:4]([OH:5])[CH2:3]1.[C:11]1([C:17](Cl)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CO>N1C=CC=CC=1>[C:17]([O:9][CH2:8][C@H:6]1[O:7][CH:2]([O:1][CH3:10])[CH2:3][C@@H:4]1[OH:5])([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

参加物

5

反応物 3

HCID 887MethanolHCID 6456Trityl chlorideHCID 10154128Methyl 2-deoxy-D-erythro-pentofuranoside

生成物 1

HCID 13912247Methyl 2-deoxy-5-O-(triphenylmethyl)-D-erythro-pentofuranoside

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

To a solution of 11.2 g (0.07 mole) of methyl 2-deoxyribofuranoside (90% pure) in 60 ml of dry pyridine under a dry nitrogen atmosphere were added 19.0 g (0.07 mole) of triphenylmethyl chloride. The mixture was stirred at ambient temperature for three days. Methanol (35 ml) was then added. The solvents were then evaporated under reduced pressure. The residue was taken up in 200 ml of ethyl acetate, washed with 75 ml of 5% sodium bicarbonate followed by a 75 ml wash with DI (deionized) water. The organic layer was dried (Na2SO4), filtered and the solvent removed under vacuum affording a sticky, viscous oil. This crude methyl 2-deoxy-5-O-tritylriboruanoside compound was used without further purification in subsequent synthetic procedures.

後処理

  1. customThe solvents were then evaporated under reduced pressure
  2. washwashed with 75 ml of 5% sodium bicarbonate
  3. washwash with DI (deionized) water
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvent removed under vacuum
  7. customaffording a sticky, viscous oil
  8. customThis crude methyl 2-deoxy-5-O-tritylriboruanoside compound was used without further purification in subsequent synthetic procedures

出典と根拠

ORDレコード
ord-ceaee069a7f34363861c0da5be98141e
出典データセット
uspto-grants-1990_02
特許番号
US04898936

反応ノート

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