Benzyl Alcohol → Benzyl 2,3,4-tri-O-acetyl-alpha-D-lyxopyranoside

HRID 964863ノート

反応式

HRID 964863 の反応式
[C:1]([O:4][C@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[CH2:8][O:7][C@@H:6]1Br)(=[O:3])[CH3:2].[CH2:20]([OH:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[Hg]C#N>C(#N)C.[Hg]Br>[C:1]([O:4][C@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[CH2:8][O:7][C@@H:6]1[O:27][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:3])[CH3:2]

参加物

6

反応物 3

HCID 244Benzyl AlcoholHCID 130488932,3,4-tri-O-acetyl-alpha-lyxopyranosyl bromideHCID 14367217Cyanide mercury

生成物 1

HCID 67638320Benzyl 2,3,4-tri-O-acetyl-alpha-D-lyxopyranoside収率 96.1%

試薬・触媒・溶媒 2

HCID 24830Mercury bromide触媒HCID 6342Acetonitrile溶媒

実験手順

A solution of compound 2 (21 g, 61.9 mmol) in acetonitrile (200 ml) and benzyl alcohol (9.6 ml, 92.3 mmol) was vigorously stirred with molecular sieves (4 Å, 25 g), mercury bromide (25 g, 69.4 mmol), mercury cyanide (18.2 g, 12.0 mmol) under argon for 18 hours. The organic layer was filtered through celite and diluted with dichloromethane (250 ml) which was washed with water, aq. NaHCO3 and aq. NaCl and dried (Na2 SO4). The solvent was filtered and then evaporated under reduced pressure. The syrupy residue was chromatographed on silica gel (filter technique) using 1.5:1 hexane-ethyl acetate to give 3 (21.8 g, 90.0%).

後処理

  1. filtrationThe organic layer was filtered through celite
  2. additiondiluted with dichloromethane (250 ml) which
  3. washwas washed with water, aq. NaHCO3 and aq. NaCl
  4. customdried (Na2 SO4)
  5. filtrationThe solvent was filtered
  6. customevaporated under reduced pressure
  7. customThe syrupy residue was chromatographed on silica gel (filter technique)

出典と根拠

ORDレコード
ord-d563b2c918d148debb74d76c47142d92
出典データセット
uspto-grants-1998_06
特許番号
US05773239

反応ノート

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