Methyl Glycolate → 1-o-Methyloxycarbonylmethyl-2,3,4,6-tetra-o-acetyl-glucopyranose

HRID 2307733

反応式

HRID 2307733 の反応式
[CH3:1][C:2]([O:4][CH2:5][C@H:6]1[O:11][C@H:10](Br)[C@H:9]([O:13][C:14]([CH3:16])=[O:15])[C@@H:8]([O:17][C:18]([CH3:20])=[O:19])[C@@H:7]1[O:21][C:22]([CH3:24])=[O:23])=[O:3].[CH3:25][O:26][C:27](=[O:30])[CH2:28][OH:29]>[Hg]=O.[Hg](Br)Br>[CH3:25][O:26][C:27]([CH2:28][O:29][CH:10]1[O:11][C@H:6]([CH2:5][O:4][C:2](=[O:3])[CH3:1])[C@@H:7]([O:21][C:22](=[O:23])[CH3:24])[C@H:8]([O:17][C:18](=[O:19])[CH3:20])[C@H:9]1[O:13][C:14](=[O:15])[CH3:16])=[O:30]

参加物

5

反応物 2

HCID 66774Methyl GlycolateHCID 101776alpha-D-Glucopyranosyl bromide, tetraacetate

生成物 1

HCID 207447381-o-Methyloxycarbonylmethyl-2,3,4,6-tetra-o-acetyl-glucopyranose収率 60%

試薬・触媒・溶媒 2

HCID 24612Mercury dibromide触媒HCID 30856Mercuric oxide触媒

実験手順

The yields of the compounds of general formula I, which can be achieved with the process according to the invention, are good. For known compounds in which a comparison with the prior art is possible, they exceed the yields of the prior art. Thus, for example, (WO 96/35700), in the reaction of acetobromoglucose with glycolic acid methyl ester under the influence of mercury oxide and mercury(II) bromide according to Koenigs-Knorr, the 1-O-methyloxycarbonylmethyl-2,3,4,6-tetra-O-acetyl-glucopyranose is obtained with a yield of 60%. The saponification to the free acid would be connected with a further loss in yield. EP 882733 also describes the production of this compound, but without yield information. According to the process of the invention, the acid is also obtained in a two-stage process. Here, the yield is 78%, however (Example 24 of this application).

後処理

  1. customThe yields of the compounds of general formula I, which
  2. customyields of the prior art

出典と根拠

ORDレコード
ord-80430e322fcc4d44bda2ed881baf8ab4
出典データセット
uspto-grants-2004_12
特許番号
US06831164B2

関連ノート

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