methyl 2,3,6-tri-O-benzoyl-4-O-mesyl-α-D-galactopyranoside | 4137-34-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,6-tri-O-benzoyl-4-O-mesyl-α-D-galactopyranoside
• 英文别名: methyl 2,3,6-tri-O-benzoyl-4-O-methanesulfonyl-alpha-d-galactopyranoside；[(2R,3S,4R,5R,6S)-4,5-dibenzoyloxy-6-methoxy-3-methylsulfonyloxyoxan-2-yl]methyl benzoate
• CAS: 4137-34-2
• 化学式: C₂₉H₂₈O₁₁S
• 分子量: 584.601
• InChiKey: BZZKVTLAQUOKQK-HGQALCJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  41
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  149
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl 2,3,6-tri-O-benzoyl-4-O-mesyl-α-D-galactopyranoside 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以72.7%的产率得到methyl 4-azido-2,3,6-tri-O-benzoyl-4-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of 4-deoxy-d-xylo-hexose and 4-azido-4-deoxy-d-glucose and their effects on lactose synthase

  摘要：

  Syntheses are reported of 4-deoxy-D-xylo-hexose and 4-azido-4-deoxy-D-glucose as potential inhibitors for lactose synthase [uridine 5'-(alpha-D-galactopyranosyl pyrophosphate):D-glucose 4-beta-D-galactopyranosyltransferase, EC 2.4.1.22]. These syntheses involved SN2 displacement of the 4-methylsulfonyloxy group of methyl 2,3,6-tri-O-benzoyl-4-O-methylsulfonyl-alpha-D-galactopyranoside by iodide and azide ions. In both cases, inversion in configuration was observed. The resulting intermediates, methyl 2,3,6-tri-O-benzoyl-4-deoxy-4-iodo-alpha-D-glucopyranoside and methyl 4-azido-2,3,6-tri-O-benzoyl-4-deoxy-alpha-D-glucopyranoside, were obtained in crystalline form. Both 4-deoxy-D-xylo-hexose and 4-azido-4-deoxy-D-glucose were found to be inhibitors for lactose synthase in the presence of alpha-lactalbumin, but had no effect in the absence of alpha-lactalbumin. Both D-glucose analogues bind to the enzyme system far more weakly than D-glucose, suggesting that the recognition of the 4-OH group of the acceptor substrate is an important factor in binding.

  DOI：

  10.1016/s0008-6215(00)85655-4
• 作为产物：
  描述：

  甲基-D-半乳糖苷-2,3,6-三苯甲酸酯 、 甲基磺酸酐 在 吡啶 作用下， 生成 methyl 2,3,6-tri-O-benzoyl-4-O-mesyl-α-D-galactopyranoside
  参考文献：
  名称：

  巯基乳糖（4-S-β-d-吡喃半乳糖基-4-硫代-d-吡喃葡萄糖）的合成

  摘要：

  摘要通过两种途径合成了潜在的酶诱导剂4- S-β-d-吡喃半乳糖基-4-硫代-d-吡喃葡萄糖，巯基乳糖（20）。从甲基α-d-吡喃半乳糖苷以高收率获得中间体2,3,6-三-O-苯甲酰基-4-S-氰基-4-硫代-α-d-吡喃葡萄糖苷（5）。衍生自5的甲基4-硫代-α-d-吡喃葡萄糖苷钠盐与2,3,4,6-四-O-乙酰基-α-d-吡喃半乳糖基溴化物在六甲基磷酸三酰胺中的反应生成甲基硫代乳糖苷衍生物可以被选择性地苯甲酰化，得到2,6，-二-O-苯甲酰基-S-（2,3,4,6-四-O-乙酰基-β-d-吡喃半乳糖基）-4-硫代-α-d-吡喃葡萄糖苷（14），直接从偶联反应中生成的复杂混合物产物中结晶出来。

  DOI：

  10.1016/s0008-6215(00)85599-8

文献信息

• Catalytic deacylation of sugars with strong base ion-exchange resins; an alternative to the Zemplén procedure
  作者：Lawrence A. Reed、Prabhakar A. Risbood、Leon Goodman

  DOI：10.1039/c39810000760

  日期：——

  Strong base ion-exchange resins may be used for the catalytic deacylation of sugars; this new technique permits the facile isolation of water-soluble products without deionization.

  强碱离子交换树脂可用于糖的催化脱酰反应。这项新技术可轻松分离水溶性产品而无需去离子。
• Classen, Arnold; Scharf, Hans-Dieter, Liebigs Annalen der Chemie, 1993, # 2, p. 183 - 188
  作者：Classen, Arnold、Scharf, Hans-Dieter

  DOI：——

  日期：——
• Synthesis of thiolactose (4-S-β-d-galactopyranosyl-4-thio-d-glucopyranose)
  作者：Lawrence A. Reed、Leon Goodman

  DOI：10.1016/s0008-6215(00)85599-8

  日期：1981.7

  methyl thiolactoside derivative that could be selectively benzoylated to give 2,6,-di- O -benzoyl- S -(2,3,4,6-tetra- O -acetyl-β- d -galactopyranosyl)-4-thio-α- d -glucopyranoside ( 14 ), which was directly crystallized from a complex mixture of products produced in the coupling reaction. Selective acetolysis of the methyl glycoside linkage of 14 (or of the derived heptaacetate), followed by transesterification

  摘要通过两种途径合成了潜在的酶诱导剂4- S-β-d-吡喃半乳糖基-4-硫代-d-吡喃葡萄糖，巯基乳糖（20）。从甲基α-d-吡喃半乳糖苷以高收率获得中间体2,3,6-三-O-苯甲酰基-4-S-氰基-4-硫代-α-d-吡喃葡萄糖苷（5）。衍生自5的甲基4-硫代-α-d-吡喃葡萄糖苷钠盐与2,3,4,6-四-O-乙酰基-α-d-吡喃半乳糖基溴化物在六甲基磷酸三酰胺中的反应生成甲基硫代乳糖苷衍生物可以被选择性地苯甲酰化，得到2,6，-二-O-苯甲酰基-S-（2,3,4,6-四-O-乙酰基-β-d-吡喃半乳糖基）-4-硫代-α-d-吡喃葡萄糖苷（14），直接从偶联反应中生成的复杂混合物产物中结晶出来。
• Synthesis of 4-deoxy-d-xylo-hexose and 4-azido-4-deoxy-d-glucose and their effects on lactose synthase
  作者：Sudhir K. Sinha、Keith Brew

  DOI：10.1016/s0008-6215(00)85655-4

  日期：1980.5

  Syntheses are reported of 4-deoxy-D-xylo-hexose and 4-azido-4-deoxy-D-glucose as potential inhibitors for lactose synthase [uridine 5'-(alpha-D-galactopyranosyl pyrophosphate):D-glucose 4-beta-D-galactopyranosyltransferase, EC 2.4.1.22]. These syntheses involved SN2 displacement of the 4-methylsulfonyloxy group of methyl 2,3,6-tri-O-benzoyl-4-O-methylsulfonyl-alpha-D-galactopyranoside by iodide and azide ions. In both cases, inversion in configuration was observed. The resulting intermediates, methyl 2,3,6-tri-O-benzoyl-4-deoxy-4-iodo-alpha-D-glucopyranoside and methyl 4-azido-2,3,6-tri-O-benzoyl-4-deoxy-alpha-D-glucopyranoside, were obtained in crystalline form. Both 4-deoxy-D-xylo-hexose and 4-azido-4-deoxy-D-glucose were found to be inhibitors for lactose synthase in the presence of alpha-lactalbumin, but had no effect in the absence of alpha-lactalbumin. Both D-glucose analogues bind to the enzyme system far more weakly than D-glucose, suggesting that the recognition of the 4-OH group of the acceptor substrate is an important factor in binding.