Hydrogen Bromide → 1,2,4,6-tetra-O-acetyl-3-O-benzyl-beta-D-glucopyranose

HRID 1746240ノート

反応式

HRID 1746240 の反応式
Br.[C:2]([O:5][C@H:6]1[O:27][C@H:26]([CH2:28][O:29][C:30](=[O:32])[CH3:31])[C@@H:21]([O:22][C:23](=[O:25])[CH3:24])[C@H:12]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C@H:7]1[O:8][C:9](=[O:11])[CH3:10])(=[O:4])[CH3:3]>C(O)(=O)C>[C:2]([O:5][C@@H:6]1[O:27][C@H:26]([CH2:28][O:29][C:30](=[O:32])[CH3:31])[C@@H:21]([O:22][C:23](=[O:25])[CH3:24])[C@H:12]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C@H:7]1[O:8][C:9](=[O:11])[CH3:10])(=[O:4])[CH3:3]

参加物

4

反応物 2

HCID 260Hydrogen BromideHCID 21637718HCID 21637718、化合物

生成物 1

HCID 111129491,2,4,6-tetra-O-acetyl-3-O-benzyl-beta-D-glucopyranose収率 101.4%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
0 °C

実験手順

Hydrogen bromide (33% solution in acetic acid) (100 mL) was slowly added to the 69 g of 1,2,4,6-tetra-O-acetyl-3-O-benzyl-α-D-glucopyranose from Step 4 and cooled to 0° C. to produce a solution of 1,2,4,6-tetra-O-acetyl-3-O-benzyl-β-D-glucopyranose (70 g) in acetic acid (140 mL). The mixture was stirred at 0° C. for 1 hour and then diluted with chloroform (1 L). Next, the reaction mixture was washed with water and saturated sodium bicarbonate and then dried over sodium sulfate. The drying agent and solvent were removed to obtain crude 2,4,6-tri-O-acetyl-3-O-benzyl-α-D-glucosyl bromide. The product was used in the next step without further purification. Additional information about this step appears in Journal of Organic Chemistry, 1962, 3089-3092. The entire article is incorporated herein by reference.

出典と根拠

ORDレコード
ord-857144665ef349fa85ee0d14cacc6425
出典データセット
uspto-grants-2015_10
特許番号
US09149489B2

反応ノート

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