Sodium Methoxide → benzyl 2-azido-2,4-dideoxy-4-fluoro-beta-D-mannopyranoside

HRID 560963ノート

反応式

HRID 560963 の反応式
[N:1]([C@H:4]1[C@@H:17]([O:18]C(=O)C(C)(C)C)[C@H:16]([F:25])[C@@H:15]([CH2:26][O:27]C(=O)C(C)(C)C)[O:14][C@H:5]1[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[N+:2]=[N-:3].C[O-].[Na+]>CO>[N:1]([C@H:4]1[C@@H:17]([OH:18])[C@H:16]([F:25])[C@@H:15]([CH2:26][OH:27])[O:14][C@H:5]1[O:6][CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)=[N+:2]=[N-:3]

参加物

4

反応物 2

HCID 10942334Sodium MethoxideHCID 86600947Benzyl 2-azido-2,4-dideoxy-4-fluoro-3,6-di-O-pivaloyl-beta-D-mannopyranoside

生成物 1

HCID 86600946benzyl 2-azido-2,4-dideoxy-4-fluoro-beta-D-mannopyranoside

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
40 °C

実験手順

Compound (22) (180 mg, 0.387 mmol) was dissolved in methanol (8 ml), sodium methoxide (922 mg, 9.67 mmols) was added to the solution, and the mixture was reacted with stirring at 40° C. TLC revealed 4.5 hours later that the reaction mixture collected into a spot, and the mixture was neutralized with a cation-exchange resin IR-120(+), followed by filtration and concentration. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1), giving Compound (23) (in an amount of 105.3 mg, 91.6% in yield).

後処理

  1. customthe mixture was reacted
  2. customcollected into a spot
  3. filtrationfollowed by filtration and concentration
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1)

出典と根拠

ORDレコード
ord-ce070ab5e9e94afd946c45e281058545
出典データセット
uspto-grants-2011_11
特許番号
US08063202B2

反応ノート

読み込み中…