Methanesulfonic acid (S)-2-benzyloxy-2-((2R,3S,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-ethyl ester | 201135-17-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methanesulfonic acid (S)-2-benzyloxy-2-((2R,3S,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-ethyl ester
• CAS: 201135-17-3
• 化学式: C₃₇H₄₂O₉S
• 分子量: 662.801
• InChiKey: ZKGBQUZGBORYIT-JVZIWWEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.68
• 重原子数：
  47.0
• 可旋转键数：
  17.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  98.75
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  Methanesulfonic acid (S)-2-benzyloxy-2-((2R,3S,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-ethyl ester 在 草酰氯 、 ammonium acetate 、 sodium acetate 、 sodium cyanoborohydride 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 517.0h， 生成
  参考文献：
  名称：

  Toward a transition state analog inhibitor of N-acetylglucosaminyl transferase V

  摘要：

  The tumor related enzyme N-acetylglucosaminyltransferase V catalyzes the transfer of GlcNAc to OH-6 of branching Man to give complex oligosaccharide structures, A transition state analog inhibitor of this enzyme was designed and a model compound was synthesized to illustrate the feasibility of the synthetic strategy. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)10087-7
• 作为产物：
  描述：

  methyl 2,3,4-tri-O-benzyl-7,8-dideoxy-α-D-manno-oct-7-enopyranoside 以 吡啶 为溶剂， 反应 3.0h， 生成 Methanesulfonic acid (S)-2-benzyloxy-2-((2R,3S,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-ethyl ester
  参考文献：
  名称：

  Toward a transition state analog inhibitor of N-acetylglucosaminyl transferase V

  摘要：

  The tumor related enzyme N-acetylglucosaminyltransferase V catalyzes the transfer of GlcNAc to OH-6 of branching Man to give complex oligosaccharide structures, A transition state analog inhibitor of this enzyme was designed and a model compound was synthesized to illustrate the feasibility of the synthetic strategy. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)10087-7

文献信息

• A General Strategy to Synthesize ADP-7-Azido-heptose and ADP-Azido-mannoses and Their Heptosyltransferase Binding Properties
  作者：Tianlei Li、Abdellatif Tikad、Huixiao Fu、Jozafina Milicaj、Colleen D. Castro、Marine Lacritick、Weidong Pan、Erika A. Taylor、Stéphane P. Vincent

  DOI：10.1021/acs.orglett.1c00048

  日期：2021.3.5

  The multistep synthesis of a novel ADP-7-azido-7-deoxy-l-glycero-β-d-manno-heptopyranoside 2a and several analogues as heptosyltransferase ligands is described. The synthesis of the key intermediate heptoside-1-β-phosphate 3a involved a β-stereoselective phosphorylation of lactol 4 employing diallyl chlorophosphate as a phosphorylating reagent. Five deprotected nucleotide sugars were generated by this

  一种新颖的ADP -7-叠氮基-7-脱氧的多步合成升-甘油基-β- d -甘露-heptopyranoside 2A和几个类似物作为配体heptosyltransferase描述。关键中间体heptoside-1-β-磷酸盐的合成图3a涉及乳醇的β立体选择性磷酸化4使用二烯丙基氯代磷酸酯作为磷酸化试剂。通过该合成序列产生了五个去保护的核苷酸糖，并将其评估为庚糖基转移酶底物（K M，k cat）。