methyl 3-(β-D-glucopyranosylthio)propanoate | 1138439-36-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-(β-D-glucopyranosylthio)propanoate
• 英文别名: methyl 3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanylpropanoate
• CAS: 1138439-36-7
• 化学式: C₁₀H₁₈O₇S
• 分子量: 282.315
• InChiKey: UIDSGXVWYINELE-HOQQJHGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  142
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  methyl 3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylthio)propanoate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以96%的产率得到methyl 3-(β-D-glucopyranosylthio)propanoate
  参考文献：
  名称：

  Synthesis of anomeric sulfonamides and their behaviour under radical-mediated bromination conditions

  摘要：

  O-Peracetylated methyl 3-(D-glycopyranosylthio)propanoates of beta-D-gluco, and alpha- and beta-D-galacto configurations were oxidized to the corresponding S,S-dioxides (sulfones) by Oxone (R) or MCPBA. Oxidation of the beta-D-gluco derivative with H2O2/Na2WO4 gave the corresponding S-oxide (sulfoxide). DBU-induced elimination of methyl acrylate from the P-D-gluco and P-D-galacto configured SS-dioxides (sulfones) gave O-peracetylated beta-D-glycopyranosyl-1-C-sulfinates which, on treatment with H2NOSO3H, furnished the corresponding beta-D-glycopyranosyl-1-C-sulfonamides. Radical-mediated bromination of the protected methyl 3-(beta-D-glycopyranosylthio)propanoate S.S-dioxides gave mixtures of 1-C- and 5-C-bromoglycosyl compounds. Similar brominations of the O-peracetylated beta-D-glycopyranosyl-1-C-sulfonamides resulted in the formation Of U-D-glycopyranosyl bromides and 1-C- and 5-C-bromoglycosyl sulfonamides. A rationale for these observations was proposed. Methyl 3-(beta-D-glucopyranosylthio)propanoate, its S,S-dioxide, and beta-D-glucopyranosyl-1-C-sulfonamide proved inefficient when tested as inhibitors of rabbit muscle glycogen phosphorylase b. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.11.002

文献信息

• Synthesis of anomeric sulfonamides and their behaviour under radical-mediated bromination conditions
  作者：Katalin Czifrák、László Somsák

  DOI：10.1016/j.carres.2008.11.002

  日期：2009.2

  O-Peracetylated methyl 3-(D-glycopyranosylthio)propanoates of beta-D-gluco, and alpha- and beta-D-galacto configurations were oxidized to the corresponding S,S-dioxides (sulfones) by Oxone (R) or MCPBA. Oxidation of the beta-D-gluco derivative with H2O2/Na2WO4 gave the corresponding S-oxide (sulfoxide). DBU-induced elimination of methyl acrylate from the P-D-gluco and P-D-galacto configured SS-dioxides (sulfones) gave O-peracetylated beta-D-glycopyranosyl-1-C-sulfinates which, on treatment with H2NOSO3H, furnished the corresponding beta-D-glycopyranosyl-1-C-sulfonamides. Radical-mediated bromination of the protected methyl 3-(beta-D-glycopyranosylthio)propanoate S.S-dioxides gave mixtures of 1-C- and 5-C-bromoglycosyl compounds. Similar brominations of the O-peracetylated beta-D-glycopyranosyl-1-C-sulfonamides resulted in the formation Of U-D-glycopyranosyl bromides and 1-C- and 5-C-bromoglycosyl sulfonamides. A rationale for these observations was proposed. Methyl 3-(beta-D-glucopyranosylthio)propanoate, its S,S-dioxide, and beta-D-glucopyranosyl-1-C-sulfonamide proved inefficient when tested as inhibitors of rabbit muscle glycogen phosphorylase b. (C) 2008 Elsevier Ltd. All rights reserved.