phenyl 2,3-di-O-benzyl-4,6-O-(di-tert-butylsilylene)-1-thio-α-D-mannopyranoside | 1555483-67-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2,3-di-O-benzyl-4,6-O-(di-tert-butylsilylene)-1-thio-α-D-mannopyranoside
• 英文别名: (4aR,6R,7S,8R,8aR)-2,2-ditert-butyl-7,8-bis(phenylmethoxy)-6-phenylsulfanyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasiline
• CAS: 1555483-67-4
• 化学式: C₃₄H₄₄O₅SSi
• 分子量: 592.872
• InChiKey: CICBATZHQGPWHV-DSSMMGBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.13
• 重原子数：
  41
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  71.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  甲基2,3,6-三-O-苄基-ALPHA-D-吡喃葡萄糖苷 、 phenyl 2,3-di-O-benzyl-4,6-O-(di-tert-butylsilylene)-1-thio-α-D-mannopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以50%的产率得到
  参考文献：
  名称：

  β-Selective Mannosylation with a 4,6-Silylene-Tethered Thiomannosyl Donor

  摘要：

  Mannosylations using the new conformationally restricted donor phenyl 2,3-di-O-benzyl-4,6-O-(di-tert-butylsilylene)-1-thio-alpha-D-mannopyranoside (6) have been found to be beta-selective with a variety of activation conditions. The simplest activation conditions were NIS/TfOH, in which case it is proposed that the beta-mannoside is formed from beta-selective glycosylation of the oxocarbenium ion 25 in a B-2,B-5 conformation.

  DOI：

  10.1021/ol403722f
• 作为产物：
  描述：

  二叔丁基硅基双(三氟甲烷磺酸) 在 吡啶 、 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 phenyl 2,3-di-O-benzyl-4,6-O-(di-tert-butylsilylene)-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  β-Selective Mannosylation with a 4,6-Silylene-Tethered Thiomannosyl Donor

  摘要：

  Mannosylations using the new conformationally restricted donor phenyl 2,3-di-O-benzyl-4,6-O-(di-tert-butylsilylene)-1-thio-alpha-D-mannopyranoside (6) have been found to be beta-selective with a variety of activation conditions. The simplest activation conditions were NIS/TfOH, in which case it is proposed that the beta-mannoside is formed from beta-selective glycosylation of the oxocarbenium ion 25 in a B-2,B-5 conformation.

  DOI：

  10.1021/ol403722f

文献信息

• DIDMH in combination with triflic acid - A new promoter system for thioglycoside glycosyl donors
  作者：Mads Heuckendorff、Henrik H. Jensen

  DOI：10.1016/j.carres.2017.11.012

  日期：2018.1

  We have explored the possibility of using 1,3-diiodo-5,5-dimethylhydantoin (DIDMH) as an alternative to N-iodosuccinimide (NIS) for activation of glycosyl donors of the thioglycoside type in various glycosylation reactions. DIDMH was found to match NIS when it comes to the capability to activate thioglycosides and provide glycosylation products in good yields. Notably, with the two equivalents of reactive

  我们已经探索了在各种糖基化反应中使用1,3-二碘-5,5-二甲基乙内酰脲（DIDMH）替代N-碘琥珀酰亚胺（NIS）来活化硫代糖苷类型糖基供体的可能性。在激活硫糖苷和提供高收率糖基化产物的能力方面，发现DIDMH与NIS相匹配。值得注意的是，每个DIDMH分子具有两个当量的反应性碘鎓离子，因此只需添加较少的质量即可使该活化剂在经济上成为NIS的替代原子。此外，发现DIDMH可以在储存数周后保持稳定，并且价格与NIS相当。掌握了这些知识后，我们因此鼓励糖类社区考虑使用DIDMH在糖基化反应中激活硫糖苷。
• β-Selective Mannosylation with a 4,6-Silylene-Tethered Thiomannosyl Donor
  作者：Mads Heuckendorff、Jesper Bendix、Christian M. Pedersen、Mikael Bols

  DOI：10.1021/ol403722f

  日期：2014.2.21

  Mannosylations using the new conformationally restricted donor phenyl 2,3-di-O-benzyl-4,6-O-(di-tert-butylsilylene)-1-thio-alpha-D-mannopyranoside (6) have been found to be beta-selective with a variety of activation conditions. The simplest activation conditions were NIS/TfOH, in which case it is proposed that the beta-mannoside is formed from beta-selective glycosylation of the oxocarbenium ion 25 in a B-2,B-5 conformation.