Methanol → methyl 4-O-(2,3,6-tri-O-benzyl-4-deoxy-4-hydroxymethyl-alpha-D-glucopyranosyl)-2,3,6-tri-O-benzyl-alpha-D-glucopyranoside

HRID 466908

反応式

HRID 466908 の反応式
[CH2:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:13]([CH2:23][O:24]C(=O)C)[C@@H:12]([CH2:28][O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[O:11][C@@H:10]1[O:37][C@@H:38]1[C@@H:45]([CH2:46][O:47][CH2:48][C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[O:44][C@H:41]([O:42][CH3:43])[C@H:40]([O:55][CH2:56][C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[C@H:39]1[O:63][CH2:64][C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.C[O-].[Na+]>C1(C)C=CC=CC=1>[CH2:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C@H:13]([CH2:23][OH:24])[C@@H:12]([CH2:28][O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[O:11][C@@H:10]1[O:37][C@@H:38]1[C@@H:45]([CH2:46][O:47][CH2:48][C:49]2[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=2)[O:44][C@H:41]([O:42][CH3:43])[C@H:40]([O:55][CH2:56][C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[C@H:39]1[O:63][CH2:64][C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 54010971Methyl 4-O-(2,3,6-tri-O-benzyl-4-deoxy-4-acetyloxymethy-alpha-D-glucopyranosyl)-2,3,6-tri-O-benzyl-alpha-D-glucopyranoside

生成物 1

HCID 53787003methyl 4-O-(2,3,6-tri-O-benzyl-4-deoxy-4-hydroxymethyl-alpha-D-glucopyranosyl)-2,3,6-tri-O-benzyl-alpha-D-glucopyranoside

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

Methyl 4-O-(2,3,6-tri-O-benzyl-4-deoxy-4-acetyloxymethy-α-D-glucopyranosyl)-2,3,6-tri-O-benzyl-α-D-glucopyranoside (3.19 g, 3.35 mmol) is dissolved in hot toluene (20 mL) and methanol (80 mL) is added, followed by a few drops of 1 M. methanolic sodium methoxide. The mixture is stirred at room temperature during 2 h. The reaction mixture is made neutral with Amberlite IR 120 (H+) resin, filtered and concentrated under reduced pressure so as to afford methyl 4-O-(2,3,6-tri-O-benzyl-4-deoxy-4-hydroxymethyl-α-D-glucopyranosyl)-2,3,6-tri-O-benzyl-α-D-glucopyranoside as an amorphous solid.

後処理

  1. filtrationfiltered
  2. concentrationconcentrated under reduced pressure so as

出典と根拠

ORDレコード
ord-99369ba750c54c1892470b47280e79a8
出典データセット
uspto-grants-1992_10
特許番号
US05157116

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