phenyl 4,6-O-benzylidene-3-O-benzyl-2-O-chloroacetyl-1-thio-β-D-glucopyranoside | 904319-28-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 4,6-O-benzylidene-3-O-benzyl-2-O-chloroacetyl-1-thio-β-D-glucopyranoside
• 英文别名: [(2R,4aR,6S,7R,8S,8aR)-2-phenyl-8-phenylmethoxy-6-phenylsulfanyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl] 2-chloroacetate
• CAS: 904319-28-4
• 化学式: C₂₈H₂₇ClO₆S
• 分子量: 527.038
• InChiKey: FBBWKIHHEUACRJ-CKUXGKHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  88.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  phenyl 4,6-O-benzylidene-3-O-benzyl-2-O-chloroacetyl-1-thio-β-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 、 碳酸氢钠 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.5h， 生成 2-(trimethylsilyl)ethyl 4,6-O-benzylidene-2-O-benzoyl-3-O-benzyl-β-D-mannopyranosyl-(1->4)-2-O-benzoyl-6-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of a novel glycosphingolipid from the millipede, Parafontaria laminata armigera, and the assembly of its carbohydrate moiety into multivalent structures

  摘要：

  A novel glycosphingolipid, beta-D-Manp-(1 -> 4)-[alpha-L-Fucp-(1 -> 3)]-beta-D-Glcp-(1 -> 1)-Cer, found in the millipede, Parafontaria laminata armigera, and multivalent derivatives of its carbohydrate moiety were synthesized. As the key step, the target glycolipid (1) was obtained through an inversion reaction at the 2-position of a beta-glucopyranoside residue yielding a P-mannopyranoside. In addition, the synthesis of fluorescently labeled trimer and tetramer glycoconjugates (2, 3) was achieved by iterative amide bond formation using a monomer unit (24). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.04.019
• 作为产物：
  描述：

  苯基-4,6-O-苯亚甲基-1-硫代-Β-D-吡喃葡萄糖苷 在 二正丁基氧化锡 作用下， 以 吡啶 、 二氯甲烷 、 苯 为溶剂， 反应 12.0h， 生成 phenyl 4,6-O-benzylidene-3-O-benzyl-2-O-chloroacetyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of a novel glycosphingolipid from the millipede, Parafontaria laminata armigera, and the assembly of its carbohydrate moiety into multivalent structures

  摘要：

  A novel glycosphingolipid, beta-D-Manp-(1 -> 4)-[alpha-L-Fucp-(1 -> 3)]-beta-D-Glcp-(1 -> 1)-Cer, found in the millipede, Parafontaria laminata armigera, and multivalent derivatives of its carbohydrate moiety were synthesized. As the key step, the target glycolipid (1) was obtained through an inversion reaction at the 2-position of a beta-glucopyranoside residue yielding a P-mannopyranoside. In addition, the synthesis of fluorescently labeled trimer and tetramer glycoconjugates (2, 3) was achieved by iterative amide bond formation using a monomer unit (24). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.04.019

文献信息

• Total Synthesis of the Lipid-Anchor-Attached Core Trisaccharides of Lipoteichoic Acids of <i>Streptococcus pneumoniae</i> and <i>Streptococcus oralis</i> Uo5
  作者：Balasaheb K. Ghotekar、Ananda Rao Podilapu、Suvarn S. Kulkarni

  DOI：10.1021/acs.orglett.9b04264

  日期：2020.1.17

  Herein we report an efficient total synthesis of lipid-anchor-appended core trisaccharides of lipoteichoic acids of Streptococcus pneumoniae and Streptococcus oralis Uo5. The key features include the expedient synthesis of the rare sugar 2,4,6-trideoxy-2-acetamido-4-amino-d-Galp building block via one-pot sequential SN2 reactions and the α-selective coupling of d-thioglucoside with the diacyl glycerol

  在本文中，我们报告了肺炎链球菌和口腔链球菌Uo5的脂锚附体脂锚酸的核心三糖的有效全合成。关键特征包括通过一锅顺序SN2反应方便地合成稀有糖2,4,6-苯三氧基-2-乙酰氨基-4-氨基-d-Galp结构单元以及d-硫代葡萄糖苷与α-选择性偶联的α-选择性偶联二酰基甘油受体来构建通用的二糖受体，该二糖受体可用于目标分子1和2的全合成。