benzyl 2,3,4-tri-O-benzyl-α-D-xylopyranoside | 1044833-49-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2,3,4-tri-O-benzyl-α-D-xylopyranoside
• CAS: 1044833-49-9
• 化学式: C₃₃H₃₄O₅
• 分子量: 510.63
• InChiKey: SQBQTCNMRKWBAO-LVVLYVGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.32
• 重原子数：
  38.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  benzyl 2,3,4-tri-O-benzyl-α-D-xylopyranoside 在 盐酸 作用下， 以 乙腈 为溶剂， 反应 22.0h， 以85%的产率得到2,3,4-tri-O-benzyl-D-xylopyranose
  参考文献：
  名称：

  Versatile Sugar Derivatives for the Synthesis of Potential Degradable Hydrophilic‐Hydrophobic Polyurethanes and Polyureas

  摘要：

  Biodegradable polymers obtained from renewable natural sources are currently receiving increasing attention because they are an alternative to the traditional petroleum-based plastics. In the present communication we describe the synthesis of the diol monomers 2,3,4-tri-O-benzyl-L-arabinitol (ABnOH) and 2,3,4-tri-O-benzylxylitol (XBnOH), and the diamino monomers 1,5-diamino-1,5-dideoxy-2,3,4-tri-O-benzyl-L-arabinitol (ABnNH(2)) and 1,5-diamino-1,5-dideoxy-2,3,4-tri-O-benzylxylitol (XBnNH(2)), which can be used in the preparation of new potentially biodegradable sugar-based polymers. As an example, we describe the synthesis and characterization of a polyurethane [PU-(ABnOH-HMDI)] and a polyurea [PUR-(ABnNH(2)-HMDI)] by poly addition reaction of ABnOH and ABnNH(2) with 1,6-hexamethylene diisocyanate.

  DOI：

  10.1080/07328300802030878
• 作为产物：
  描述：

  溴甲苯 、 benzyl α-D-xylopyranoside 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以85%的产率得到benzyl 2,3,4-tri-O-benzyl-α-D-xylopyranoside
  参考文献：
  名称：

  Versatile Sugar Derivatives for the Synthesis of Potential Degradable Hydrophilic‐Hydrophobic Polyurethanes and Polyureas

  摘要：

  Biodegradable polymers obtained from renewable natural sources are currently receiving increasing attention because they are an alternative to the traditional petroleum-based plastics. In the present communication we describe the synthesis of the diol monomers 2,3,4-tri-O-benzyl-L-arabinitol (ABnOH) and 2,3,4-tri-O-benzylxylitol (XBnOH), and the diamino monomers 1,5-diamino-1,5-dideoxy-2,3,4-tri-O-benzyl-L-arabinitol (ABnNH(2)) and 1,5-diamino-1,5-dideoxy-2,3,4-tri-O-benzylxylitol (XBnNH(2)), which can be used in the preparation of new potentially biodegradable sugar-based polymers. As an example, we describe the synthesis and characterization of a polyurethane [PU-(ABnOH-HMDI)] and a polyurea [PUR-(ABnNH(2)-HMDI)] by poly addition reaction of ABnOH and ABnNH(2) with 1,6-hexamethylene diisocyanate.

  DOI：

  10.1080/07328300802030878

文献信息

• Synthesis of Core M3 Matriglycan Constituents via an Additive-Controlled 1,2-cis-Xylopyranosylation with O-Xylosyl Imidates as Donors
  作者：Tianlu Li、Miaomiao Zhang、Panpan Lv、Yue Yang、Richard R Schmidt、Peng Peng

  DOI：10.1021/acs.joc.3c02339

  日期：2024.1.5

  established via a preactivation-based, additive-modulated trichloroacetimidate glycosidation strategy. The current protocol is mild, practical, and successful with various xylopyranosyl donors and glycosyl acceptors, including acceptors that are reported to be less reactive due to steric hindrance. The utility of this method was demonstrated with the facile assembly of matriglycan constituent tetra- and

  通过基于预激活、加成调节的三氯乙酰亚胺酯糖苷化策略，建立了 1,2-顺式-吡喃木糖苷键形成的高度立体选择性策略。目前的方案温和、实用，并且对各种吡喃木糖基供体和糖基受体成功，包括据报道由于空间位阻而反应性较低的受体。通过基质聚糖成分四糖和六糖的轻松组装证明了该方法的实用性。