phenyl 2,6-di-O-benzoyl-β-D-galactopyranosyl-(1 -> 4)-2,3,6-tri-O-benzoyl-1-thio-β-D-glucopyranoside | 301662-92-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: phenyl 2,6-di-O-benzoyl-β-D-galactopyranosyl-(1 -> 4)-2,3,6-tri-O-benzoyl-1-thio-β-D-glucopyranoside
• 英文别名: phenyl 2,6-di-O-benzoyl-β-D-galactopyranosyl-(1-> 4)-2,3,6-tri-O-benzoyl-1-thio-β-D-glucopyranoside
• CAS: 301662-92-0
• 化学式: C₅₃H₄₆O₁₅S
• 分子量: 955.005
• InChiKey: NEDQSVNCMLKMNL-KMKQRQEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.73
• 重原子数：
  69.0
• 可旋转键数：
  16.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  199.65
• 氢给体数：
  2.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  phenyl 2,6-di-O-benzoyl-β-D-galactopyranosyl-(1 -> 4)-2,3,6-tri-O-benzoyl-1-thio-β-D-glucopyranoside 在 sodium methylate 甲醇 、 三氟化硼乙醚 、 一水合肼 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 13.0h， 生成
  参考文献：
  名称：

  Polymer-supported and chemoenzymatic synthesis of the Neisseria meningitidis pentasaccharide: a methodological comparison

  摘要：

  Neisseria meningitidis trisaccharide [GlcNAc beta(1 --> 3)Gal beta(1 --> 4)Glc-R], tetrasaccharide [Gal beta(1 --> 4)GlcNAc beta(1 --> 3)Gal beta(1 --> 4)Glc-R], and a pentasaccharide [Neu5Ac alpha(2 --> 3)Gal beta(1 --> 4)GlcNAc beta(1 --> 3)Gal beta(1 --> 4)Glc-SPh] were prepared via conventional chemical synthesis, polymer-supported synthesis, and chemoenzymatic methods, starting from D-lactose. The polymer polyethyleneglycol monomethylether (MPEG) and the linker dioxyxylene (DOX) were used with a lactose-bound acceptor to improve the purification process. Several enzymes (LgtA, GalE-LgtB fusion, and CMP-Neu5Ac synthetase/sialyltransferase fusion) were used for syntheses of these oligosaccharides. Excellent stereo- and regioselectivities as well as high yield (> 90% from Gal beta(1 --> 4)Glc-SPh) of the pentasaccharide were obtained. Both of the convenient processes are suitable for efficient preparation of target oligosaccharides. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00086-0
• 作为产物：
  描述：

  phenyl 2,6-di-O-benzoyl-3,4-di-O-isopropylidene-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-1-thio-β-D-glucopyranoside 在 盐酸 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 生成 phenyl 2,6-di-O-benzoyl-β-D-galactopyranosyl-(1 -> 4)-2,3,6-tri-O-benzoyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Polymer-supported and chemoenzymatic synthesis of the Neisseria meningitidis pentasaccharide: a methodological comparison

  摘要：

  Neisseria meningitidis trisaccharide [GlcNAc beta(1 --> 3)Gal beta(1 --> 4)Glc-R], tetrasaccharide [Gal beta(1 --> 4)GlcNAc beta(1 --> 3)Gal beta(1 --> 4)Glc-R], and a pentasaccharide [Neu5Ac alpha(2 --> 3)Gal beta(1 --> 4)GlcNAc beta(1 --> 3)Gal beta(1 --> 4)Glc-SPh] were prepared via conventional chemical synthesis, polymer-supported synthesis, and chemoenzymatic methods, starting from D-lactose. The polymer polyethyleneglycol monomethylether (MPEG) and the linker dioxyxylene (DOX) were used with a lactose-bound acceptor to improve the purification process. Several enzymes (LgtA, GalE-LgtB fusion, and CMP-Neu5Ac synthetase/sialyltransferase fusion) were used for syntheses of these oligosaccharides. Excellent stereo- and regioselectivities as well as high yield (> 90% from Gal beta(1 --> 4)Glc-SPh) of the pentasaccharide were obtained. Both of the convenient processes are suitable for efficient preparation of target oligosaccharides. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00086-0

文献信息

• Highly Efficient α‐Sialylation by Virtue of Fixed Dipole Effects of<i>N</i>‐Phthalyl Group: Application to Continuous Flow Synthesis of α(2‐3)‐and α(2‐6)‐Neu5Ac‐Gal Motifs by Microreactor
  作者：Shin‐ichi Tanaka、Takashi Goi、Katsunori Tanaka、Koichi Fukase

  DOI：10.1080/07328300701634796

  日期：2007.10

  Highly alpha-selective sialylation of sialic acid N-phenyltrifluoroacetimidate with various galactose and lactose acceptors has been achieved by introducing the C-5 N-phthalyl group on the donor. The "fixed dipole effect" of the N-phthalyl group was proposed to explain the high reactivity and a-selectivity. The microfluidic system was applied to the present alpha-sialylation, which is amenable to large-scale synthesis. The N-phthalyl group was removed by treatment with methylhydrazine acetate, for which protocol can be readily applied to the synthesis of a variety of sialic acid-containing oligosaccharides.[GRAPHICS]