methyl 4',6'-O-isopropylidene-β-lactoside | 158813-81-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4',6'-O-isopropylidene-β-lactoside
• 英文别名: (4aR,6S,7R,8R,8aR)-6-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-methoxyoxan-3-yl]oxy-2,2-dimethyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol
• CAS: 158813-81-1
• 化学式: C₁₆H₂₈O₁₁
• 分子量: 396.392
• InChiKey: XJWHFVKUIIESHZ-OAYALFPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  157
• 氢给体数：
  5
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl 4',6'-O-isopropylidene-β-lactoside 在 sodium hydride 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 34.0h， 生成 methyl 2,3,6-tri-O-benzyl-4-O-(2,3-di-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Carbohydrate-derived surfactants: synthesis and phase behaviour of methyl 4′ 6′-di-O-alkyl-β-lactosides

  摘要：

  In order to study the physical properties of lactose-derived surfactants. methyl 4',6'-di-O-hexyl-beta-lactoside and methyl 4',6'-di-O-octyl-beta-lactoside were prepared. The 4',6'-O-isopropylidene ketal was used as a temporary protecting group in the key intermediate. The 3',4'-O-benzylidene acetal was identified as a minor by-product in the preparation of methyl 4',6'-O-benzylidene-beta-lactoside by acid-catalysed transacetalation. The phase behaviour of these derivatives is reported.

  DOI：

  10.1039/p19940002103
• 作为产物：
  描述：

  2,2-二甲氧基丙烷 、 甲基 4-O-BETA-D-半乳糖基-BETA-D-吡喃葡萄糖苷 在 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以55%的产率得到methyl 4',6'-O-isopropylidene-β-lactoside
  参考文献：
  名称：

  Carbohydrate-derived surfactants: synthesis and phase behaviour of methyl 4′ 6′-di-O-alkyl-β-lactosides

  摘要：

  In order to study the physical properties of lactose-derived surfactants. methyl 4',6'-di-O-hexyl-beta-lactoside and methyl 4',6'-di-O-octyl-beta-lactoside were prepared. The 4',6'-O-isopropylidene ketal was used as a temporary protecting group in the key intermediate. The 3',4'-O-benzylidene acetal was identified as a minor by-product in the preparation of methyl 4',6'-O-benzylidene-beta-lactoside by acid-catalysed transacetalation. The phase behaviour of these derivatives is reported.

  DOI：

  10.1039/p19940002103

文献信息

• Carbohydrate-derived surfactants: synthesis and phase behaviour of methyl 4′ 6′-di-O-alkyl-β-lactosides
  作者：Virginie Langlois、J. Michael Williams

  DOI：10.1039/p19940002103

  日期：——

  In order to study the physical properties of lactose-derived surfactants. methyl 4',6'-di-O-hexyl-beta-lactoside and methyl 4',6'-di-O-octyl-beta-lactoside were prepared. The 4',6'-O-isopropylidene ketal was used as a temporary protecting group in the key intermediate. The 3',4'-O-benzylidene acetal was identified as a minor by-product in the preparation of methyl 4',6'-O-benzylidene-beta-lactoside by acid-catalysed transacetalation. The phase behaviour of these derivatives is reported.