phenyl 2,3-di-O-benzoyl-4-O-benzyl-1-thio-α-D-mannopyranoside | 1319152-36-7

• 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-benzoyl-4-O-benzyl-1-thio-α-D-mannopyranoside
• CAS: 1319152-36-7
• 化学式: C₃₃H₃₀O₇S
• 分子量: 570.663
• InChiKey: VHJRZKUHOBNPFM-DYPUGTQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.53
• 重原子数：
  41.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  91.29
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  phenyl 2,3-di-O-benzoyl-4-O-benzyl-1-thio-α-D-mannopyranoside 在 吡啶 、 甲醇 、 三氟甲磺酸三甲基硅酯 、 sodium methylate 作用下， 以 二氯甲烷 为溶剂， 生成 phenyl (2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->6)-2,3-di-O-acetyl-4-O-benzyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Experimental observations on the regioselectivity of glycosylation of a 4,6-diol system in the β-d-mannopyranosyl unit of a N-glycan pentasaccharide core structure

  摘要：

  The regioselectivity of glycosylation of a 4,6-diol system in the p-mannopyranosyl unit of a N-glycan pentasaccharide core structure is found to be strongly dependent on the structure of the glycosyl donor. While glycosylation with a 2-O-acetyl-D-mannopyranosyl trichloroacetimidate and with a D-mannopyranosyl (alpha 1 -> 3) 2-O-acetyl mannopyranosyl trichoroacetimidate regioselectively occurs at the primary OH-6 position, reaction with D-mannopyranosyl (alpha 1 -> 6) mannopyranosyl 2-O-benzoyl, 2-O-acetyl and 2-O-pivaloyl trichloroacetimidate results in approximately 1:1 mixture of regioisomers at primary OH-6 and secondary OH-4 positions. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.05.006
• 作为产物：
  描述：

  phenyl-2,3-di(O-benzoyl)-4,6-O-benzylidene-1-thio-α-D-mannopyranoside 在 硼烷四氢呋喃络合物 、 三氟甲磺酸二丁硼 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.08h， 以88%的产率得到phenyl 2,3-di-O-benzoyl-4-O-benzyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Experimental observations on the regioselectivity of glycosylation of a 4,6-diol system in the β-d-mannopyranosyl unit of a N-glycan pentasaccharide core structure

  摘要：

  The regioselectivity of glycosylation of a 4,6-diol system in the p-mannopyranosyl unit of a N-glycan pentasaccharide core structure is found to be strongly dependent on the structure of the glycosyl donor. While glycosylation with a 2-O-acetyl-D-mannopyranosyl trichloroacetimidate and with a D-mannopyranosyl (alpha 1 -> 3) 2-O-acetyl mannopyranosyl trichoroacetimidate regioselectively occurs at the primary OH-6 position, reaction with D-mannopyranosyl (alpha 1 -> 6) mannopyranosyl 2-O-benzoyl, 2-O-acetyl and 2-O-pivaloyl trichloroacetimidate results in approximately 1:1 mixture of regioisomers at primary OH-6 and secondary OH-4 positions. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.05.006

文献信息

• Direct β-Mannosylation of Primary Alcohol Acceptors: Trisaccharide Iteration Assembly of β-1,6-Oligomannosides Corresponding to Kakelokelose
  作者：Peng Wang、Junlin Wang、Wenjun Yin、Xianyang Wang、Ni Song、Sumei Ren、Ming Li

  DOI：10.1021/acs.orglett.1c04363

  日期：2022.1.28

  Gold(I)-catalyzed stereoselective β-glycosylation of primary alcohols is achieved using the orthogonally protected mannosyl α-ortho-hexynylbenzoate (OABz) donors devoid of 4,6-O-tethering groups used in conventionally constructing β-mannosidic bonds. The potential of this methodology is showcased by the first assembly of β-1,6-tri/hexa-/nonamannosides and related sulfated congeners through a convergent

  金 (I) 催化的伯醇立体选择性 β-糖基化是使用正交保护的甘露糖基 α-邻-己炔基苯甲酸酯 (OABz) 供体实现的，该供体不含用于常规构建 β-甘露糖苷键的 4,6- O-束缚基团。通过收敛策略首次组装 β-1,6-tri/hexa-/nonamannosides 和相关的硫酸化同系物展示了这种方法的潜力。该合成的特点是 α-三甘露糖基 OABz 供体的立体控制 β-糖基化和后期磺化。这项工作有望加快β-1,6-甘露聚糖和功能化衍生物的制备。