phenyl 3-O-(tert-butyldimethysilyl)-4,6-O-benzylidene-1-deoxy-1-thio-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 3-O-(tert-butyldimethysilyl)-4,6-O-benzylidene-1-deoxy-1-thio-β-D-glucopyranoside
• 英文别名: phenyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranoside；(2R,4aR,6S,7R,8R,8aR)-8-[tert-butyl(dimethyl)silyl]oxy-2-phenyl-6-phenylsulfanyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-ol
• 化学式: C₂₅H₃₄O₅SSi
• 分子量: 474.693
• InChiKey: PCXLTTZAHZSPSH-QALHXSLCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.37
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  82.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  phenyl 3-O-(tert-butyldimethysilyl)-4,6-O-benzylidene-1-deoxy-1-thio-β-D-glucopyranoside 在 三氟化硼乙醚 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 phenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->2)-[(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->3)]-4,6-O-benzylidene-1-deoxy-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  The synthesis of pennogenin 3-O-β-d-glucopyranosyl-(1 → 3)-[α-l-rhamnopyranosyl-(1 → 2)]-β-d-glucopyranoside

  摘要：

  Pennogenin 3-O-beta-D-glucopyranosyl-(1 -> 3)-[alpha-L-rhamnopyranosyl-(1 -> 2)]-beta-D-glucopyranoside, a monodesmosidic saponin isolated from Paris polyphylla Smith var. yunnanensis with promised antitumor activities, was firstly synthesized from glucoside thiol via nine steps and with 27% overall yield.

  DOI：

  10.1080/10286020.2011.653348
• 作为产物：
  描述：

  1-硫代-b-D-吡喃葡萄糖苷对甲苯酯 在 咪唑 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 phenyl 3-O-(tert-butyldimethysilyl)-4,6-O-benzylidene-1-deoxy-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  The synthesis of pennogenin 3-O-β-d-glucopyranosyl-(1 → 3)-[α-l-rhamnopyranosyl-(1 → 2)]-β-d-glucopyranoside

  摘要：

  Pennogenin 3-O-beta-D-glucopyranosyl-(1 -> 3)-[alpha-L-rhamnopyranosyl-(1 -> 2)]-beta-D-glucopyranoside, a monodesmosidic saponin isolated from Paris polyphylla Smith var. yunnanensis with promised antitumor activities, was firstly synthesized from glucoside thiol via nine steps and with 27% overall yield.

  DOI：

  10.1080/10286020.2011.653348

文献信息

• Macrolide Core Synthesis of Calysolin IX Using an Intramolecular Glycosylation Approach
  作者：Mirosław Nawój、Artur Grobelny、Jacek Mlynarski

  DOI：10.1002/ejoc.201901480

  日期：2020.1.9

  The intramolecular glycosylation acts as an efficient tool for the synthesis of a 27‐membered macrocyclic ring. This approach is highlighted in the first total synthesis of the most complex resin glycoside isolated to date – Calysolin IX.

  分子内糖基化是合成27元大环的有效工具。迄今为止，最复杂的树脂糖苷的首次全合成-卡里索林IX强调了这种方法。
• The Preparation of 1-Tributylstannyl Glycals from 1-Phenylsulfonyl Glycals via Ni(0)-Catalysed Coupling with Tributylstannylmagnesium Bromide
  作者：Andrew Gunn、Krzysztof Jarowicki、Philip Kocienski、Stephen Lockhart

  DOI：10.1055/s-2001-10802

  日期：——

  1-Phenylsulfonyl glycals undergo an easy Ni(0)-catalysed coupling with tributylstannylmagnesium bromide to give the corresponding 1-tributylstannyl glycals in good yield.

  1-苯磺酰基甘油醛与三丁基锡溴化镁容易发生 Ni(0)- 催化偶联反应，从而得到相应的 1-三丁基锡甘油醛，收率很高。
• The synthesis of pennogenin 3-O-β-<scp>d</scp>-glucopyranosyl-(1 → 3)-[α-<scp>l</scp>-rhamnopyranosyl-(1 → 2)]-β-<scp>d</scp>-glucopyranoside
  作者：Xin-Feng Luo、Fan Lei、Yi He、Shu-Chen Pei、Li Hai、Shan Qian、Yong Wu

  DOI：10.1080/10286020.2011.653348

  日期：2012.4

  Pennogenin 3-O-beta-D-glucopyranosyl-(1 -> 3)-[alpha-L-rhamnopyranosyl-(1 -> 2)]-beta-D-glucopyranoside, a monodesmosidic saponin isolated from Paris polyphylla Smith var. yunnanensis with promised antitumor activities, was firstly synthesized from glucoside thiol via nine steps and with 27% overall yield.