Octyl β-D-galactopyranoside 6-O-acetate | 221654-54-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Octyl β-D-galactopyranoside 6-O-acetate
• 英文别名: octyl 6-O-acetyl-β-D-galactopyranoside；[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-octoxyoxan-2-yl]methyl acetate
• CAS: 221654-54-2
• 化学式: C₁₆H₃₀O₇
• 分子量: 334.41
• InChiKey: JBAHDWFMGCOBEZ-LYYZXLFJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  23
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Octyl β-D-galactopyranoside 6-O-acetate 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 水 、 sodium methylate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 12.0h， 生成 octyl (5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-β-D-galactopyranoside
  参考文献：
  名称：

  Chemoenzymatic Synthesis of Ganglioside Gm4 Analogs as Potential Immunosuppressive Agents

  摘要：

  An efficient, chemoenzymatic synthesis of ganglioside GM4 analogs having a potent immunosuppressive activity is described. One-step and highly regioselective 6-O-acetylation of long-chain alkyl, 2-(trimethysilyl)ethyl and phenyl 1-thio beta-D-galactopyranosides was performed by using vinyl acetate and lipase PS. The resulting 6-O-acetates (70-93%) were sialylated with methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid)onate promoted by N-iodosuccinimide (NIS) and trifluoromethanesulfonic acid (TfOH). The 2-(trimethylsilyl)ethyl glycoside derivative was converted to the imidate which was then coupled with dodecan-1-ol, hexadecan-1-ol, and 2-(tetradecyl)hexadecan-1-ol, respectively, to give the protected GM4 derivatives (90-96%). O-Deacylation and saponification of the methyl ester gave the target ganglioside GM4 analogs in high yields.

  DOI：

  10.1080/07328309908543992
• 作为产物：
  描述：

  octyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 在 Lipase PS 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 Octyl β-D-galactopyranoside 6-O-acetate
  参考文献：
  名称：

  Chemoenzymatic Synthesis of Ganglioside Gm4 Analogs as Potential Immunosuppressive Agents

  摘要：

  An efficient, chemoenzymatic synthesis of ganglioside GM4 analogs having a potent immunosuppressive activity is described. One-step and highly regioselective 6-O-acetylation of long-chain alkyl, 2-(trimethysilyl)ethyl and phenyl 1-thio beta-D-galactopyranosides was performed by using vinyl acetate and lipase PS. The resulting 6-O-acetates (70-93%) were sialylated with methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid)onate promoted by N-iodosuccinimide (NIS) and trifluoromethanesulfonic acid (TfOH). The 2-(trimethylsilyl)ethyl glycoside derivative was converted to the imidate which was then coupled with dodecan-1-ol, hexadecan-1-ol, and 2-(tetradecyl)hexadecan-1-ol, respectively, to give the protected GM4 derivatives (90-96%). O-Deacylation and saponification of the methyl ester gave the target ganglioside GM4 analogs in high yields.

  DOI：

  10.1080/07328309908543992

文献信息

• Functionalized DMAP catalysts for regioselective acetylation of carbohydrates
  作者：Takuya Kurahashi、Tadashi Mizutani、Jun-ichi Yoshida

  DOI：10.1016/s0040-4020(02)01098-0

  日期：2002.10

  New functionalized DMAPs having carboxylic acid functionality are developed for regioselective acylation of carbohydrates. In these catalysts, DMAP (4-(N,N-dimethylamino)pyridine) is linked with –COOH (–COOMe or –OSO3H in reference catalysts) via methylene spacers of different length at the dimethylamino moiety. Utilizing one of these catalysts, 3-[N-decyl-N-(4-pyridyl)amino]propionic acid (1), regioselectivity

  具有羧酸官能团的新的官能化的DMAP被开发用于碳水化合物的区域选择性酰化。在这些催化剂中，DMAP（4-（N，N-二甲基氨基）吡啶）通过二甲氨基部分上不同长度的亚甲基间隔基与–COOH（在参考催化剂中为–COOMe或–OSO 3 H）连接。利用这些催化剂中的一种，即3- [ N-癸基-N-（4-吡啶基）氨基]丙酸（1），在1- O-辛基β-d-吡喃葡萄糖苷的乙酰化中，对于伯6-OH基团的区域选择性为：与母体DMAP相比，催化活性从16％提高到89％，催化活性大大提高。催化剂1在CHCl 3的6位上，对1- O-辛基吡喃葡萄糖苷（分别对β-和α-端基的区域选择性分别为89％和88％区域选择性）和1- O-辛基吡喃半乳糖苷（对两种异构体都为100％区域选择性）的两个异构体进行区域选择性乙酰化。但在1- O-辛基甘露吡喃糖苷的情况下，可得到4-和6-单乙酸酯的近1：1混合物。进行对照实验以研究区域控制的机械方面。
• Kurahashi, Takuya; Mizutani, Tadashi; Yoshida, Jun-Ichi, Journal of the Chemical Society. Perkin transactions I, 1999, # 4, p. 465 - 473
  作者：Kurahashi, Takuya、Mizutani, Tadashi、Yoshida, Jun-Ichi

  DOI：——

  日期：——