1-O-p-methoxyphenyl 2,3,4-tri-O-benzoyl-6-O-tert-butyldiphenylsilyl-β-D-glucopyranose | 1344980-48-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-p-methoxyphenyl 2,3,4-tri-O-benzoyl-6-O-tert-butyldiphenylsilyl-β-D-glucopyranose
• 英文别名: p-methoxyphenyl 2,3,4-tri-O-benzoyl-6-O-tert-butyldiphenylsilyl-β-D-glucopyranoside；Bz(-2)[Bz(-3)][Bz(-4)][TBDPS(-6)]Glc(b)-O-Ph(4-OMe)；[(2R,3R,4S,5R,6S)-4,5-dibenzoyloxy-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-6-(4-methoxyphenoxy)oxan-3-yl] benzoate
• CAS: 1344980-48-8
• 化学式: C₅₀H₄₈O₁₀Si
• 分子量: 837.011
• InChiKey: WKKVJMNCJKJNGL-AMYMZKMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.05
• 重原子数：
  61
• 可旋转键数：
  18
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  116
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1-O-p-methoxyphenyl 2,3,4-tri-O-benzoyl-6-O-tert-butyldiphenylsilyl-β-D-glucopyranose 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 28.5h， 生成 p-methoxyphenyl-2,3,4-tri-O-benzoyl-6-O-2’-O-(2-azidomethylbenzoyl)-3’,4’-di-O-acetyl-α-L-arabinopyranosyl-β-D-glucopyranoside
  参考文献：
  名称：

  对D环功能化细胞毒性的Oleanane型皂苷Pithedulosides D和E的合成研究。

  摘要：

  借助Schmidt和Yu糖基化的精心设计应用，实现了棘皮囊藻酸皂苷pithedulosides D和E的首次全合成，这两个抗肿瘤和具有代表性的D环功能化的齐墩果烷型皂苷。得益于所应用的收敛性合成策略，通过四个线性步骤可以合成棘孢囊酸，其总收率高达71％和76％。

  DOI：

  10.1002/ejoc.201700707
• 作为产物：
  描述：

  4-甲氧基苯基Β-D-吡喃葡萄糖苷 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 作用下， 生成 1-O-p-methoxyphenyl 2,3,4-tri-O-benzoyl-6-O-tert-butyldiphenylsilyl-β-D-glucopyranose
  参考文献：
  名称：

  An efficient and recyclable catalyst for the cleavage of tert-butyldiphenylsilyl ethers

  摘要：

  An efficient, chemoselective, and environment-friendly method for the deprotection of tert-butyldiphenylsilyl ethers mediated by triflic acid supported on silica gel is reported. A wide range of tert-butyldiphenylsilyl ethers derived from carbohydrate and saponin residues can be smoothly cleaved in the presence of various types of other protecting groups in good to excellent yields in acetonitrile. This heterogeneous reaction does not require aqueous workup, and the supported catalyst can be readily recycled. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.02.021

文献信息

• 一种茶叶香料前体糖苷及其合成方法
  申请人：山东大学

  公开号：CN111253452A

  公开（公告）日：2020-06-09

  本发明涉及一种茶叶香料前体糖苷及其合成方法，该合成方法包括合成芳醇(烷醇)‑β‑D‑葡萄糖苷与芳醇(烷醇)‑β‑D‑樱草糖苷十种糖苷的步骤。本发明是一种选择性好、产率高、成本低的糖苷合成方法。
• Synthesis of 1,6-anhydro sugars catalyzed by silica supported perchloric acid
  作者：Yuexing Chun、Shiqiang Yan、Xiangpeng Li、Ning Ding、Wei Zhang、Peng Wang、Ming Li、Yingxia Li

  DOI：10.1016/j.tetlet.2011.09.055

  日期：2011.11

  A new and efficient method for the preparation of 1,6-anhydro sugars using silica supported perchloric acid as a catalyst is described. The catalyst is heterogeneous and 1,6-anhydro sugars could be formed within a few minutes with good yields.

  描述了使用二氧化硅负载的高氯酸作为催化剂制备1，6-脱水糖的新的有效方法。该催化剂是非均相的，并且可以在几分钟内以良好的产率形成1，6-脱水糖。
• Synthetic Investigation toward the D-Ring-Functionalized Cytotoxic Oleanane-Type Saponins Pithedulosides D and E
  作者：Shi-Jie Ge、Yuan-Hong Tu、Jian-Hui Xia、Jian-Song Sun

  DOI：10.1002/ejoc.201700707

  日期：2017.7.25

  application of both Schmidt and Yu glycosylations, the first total syntheses of the echinocystic acid saponins pithedulosides D and E, the two antitumoral and representative D-ring-functionalized oleanane-type saponins, were achieved. Benefitting from the applied convergent synthetic strategy, the echinocystic acids could be synthesized in overall yields of as high as 71 and 76 % through four linear steps

  借助Schmidt和Yu糖基化的精心设计应用，实现了棘皮囊藻酸皂苷pithedulosides D和E的首次全合成，这两个抗肿瘤和具有代表性的D环功能化的齐墩果烷型皂苷。得益于所应用的收敛性合成策略，通过四个线性步骤可以合成棘孢囊酸，其总收率高达71％和76％。
• An efficient and recyclable catalyst for the cleavage of tert-butyldiphenylsilyl ethers
  作者：Shiqiang Yan、Ning Ding、Wei Zhang、Peng Wang、Yingxia Li、Ming Li

  DOI：10.1016/j.carres.2012.02.021

  日期：2012.6

  An efficient, chemoselective, and environment-friendly method for the deprotection of tert-butyldiphenylsilyl ethers mediated by triflic acid supported on silica gel is reported. A wide range of tert-butyldiphenylsilyl ethers derived from carbohydrate and saponin residues can be smoothly cleaved in the presence of various types of other protecting groups in good to excellent yields in acetonitrile. This heterogeneous reaction does not require aqueous workup, and the supported catalyst can be readily recycled. (C) 2012 Elsevier Ltd. All rights reserved.