3-O-[(tert-butyl)-diphenylsilyl]-1,2-O-isopropylidene-α-D-glucofuranose | 112421-57-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-[(tert-butyl)-diphenylsilyl]-1,2-O-isopropylidene-α-D-glucofuranose
• 英文别名: (R)-1-((3aR,5R,6S,6aR)-6-((tert-Butyldiphenylsilyl)oxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethane-1,2-diol；(1R)-1-[(3aR,5R,6S,6aR)-6-[tert-butyl(diphenyl)silyl]oxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethane-1,2-diol
• CAS: 112421-57-5
• 化学式: C₂₅H₃₄O₆Si
• 分子量: 458.627
• InChiKey: ZCDXDKZPZSMWNP-XNBWIAOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.16
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  bis(p-nitrophenyl)diazomethane 、 3-O-[(tert-butyl)-diphenylsilyl]-1,2-O-isopropylidene-α-D-glucofuranose 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以82%的产率得到(1R)-1-[(3aR,5R,6S,6aR)-6-[tert-butyl(diphenyl)silyl]oxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-[bis(4-nitrophenyl)methoxy]ethanol
  参考文献：
  名称：

  p,p'-Dinitrobenzhydryl ethers, acid and base stable protecting groups, which are readily removable in the presence of benzyl and monomethoxytrityl functions

  摘要：

  DOI：

  10.1021/jo00240a018
• 作为产物：
  描述：

  3-O-tert-butyldiphenylsilyl-1,2,5,6-di-O-isopropylidene-α-D-glucofuranose 在 phosphomolybdic acid supported on silica gel 作用下， 以 乙腈 为溶剂， 反应 0.12h， 以94%的产率得到3-O-[(tert-butyl)-diphenylsilyl]-1,2-O-isopropylidene-α-D-glucofuranose
  参考文献：
  名称：

  Phosphomolybdic Acid Supported on Silica Gel: An Efficient, Mild and Reusable Catalyst for the Chemoselective Hydrolysis of Acetonides

  摘要：

  碳水化合物乙缩醛在环境友好的负载型磷钼酸（H3PMo12O40/硅胶，简称PMA-SiO2）作用下，于室温、乙腈溶液中仅需5至7分钟即可选择性地裂解为相应的二醇。在这种反应条件下，如THP、TBS、TBDPS、MOM、OMe和PMB等对酸不稳定的保护基团均能保持稳定。

  DOI：

  10.1055/s-2005-872701

文献信息

• Phosphomolybdic Acid Supported on Silica Gel: An Efficient, Mild and Reusable Catalyst for the Chemoselective Hydrolysis of Acetonides
  作者：J. S. Yadav、S. Raghavendra、M. Satyanarayana、E. Balanarsaiah

  DOI：10.1055/s-2005-872701

  日期：——

  Carbohydrate acetonides were chemoselectively cleaved to the corresponding diols by using environmentally benign phosphomolybdic acid (H3PMo12O40) supported on silica gel (PMA-SiO2) at ambient temperature in a short span of 5-7 minutes in acetonitrile. Acid-labile protective groups such as THP, TBS, TBDPS, MOM, OMe and PMB were found to be stable under the reaction conditions.

  碳水化合物乙缩醛在环境友好的负载型磷钼酸（H3PMo12O40/硅胶，简称PMA-SiO2）作用下，于室温、乙腈溶液中仅需5至7分钟即可选择性地裂解为相应的二醇。在这种反应条件下，如THP、TBS、TBDPS、MOM、OMe和PMB等对酸不稳定的保护基团均能保持稳定。
• JUST, GEORGE;WANG, ZHI YUAN;CHAN, LAVAL, J. ORG. CHEM., 53,(1988) N 5, 1030-1033
  作者：JUST, GEORGE、WANG, ZHI YUAN、CHAN, LAVAL

  DOI：——

  日期：——
• p,p'-Dinitrobenzhydryl ethers, acid and base stable protecting groups, which are readily removable in the presence of benzyl and monomethoxytrityl functions
  作者：George Just、Zhi Yuan Wang、Laval Chan

  DOI：10.1021/jo00240a018

  日期：1988.3
• Formal synthesis of (+)-varitriol. Application of Pd(II)/Cu(II)-catalysed bicyclisation of unsaturated polyols
  作者：Miroslav Palík、Oľga Karlubíková、Daniela Lackovičová、Angelika Lásiková、Tibor Gracza

  DOI：10.1016/j.tet.2010.04.074

  日期：2010.7

  A formal and improved synthesis of natural (+)-varitriol from D-glucose and dimethyl L-tartrate, respectively, are reported. The key steps are the Pd(II)/Cu(II)-catalysed bicyclisation of O-benzyl protected triols L-xylo-15 and L-xylo-15/L-lyxo-15, respectively, followed by ring opening of intermediate dianhydro-L-gulitol 16. The syntheses of key intermediate of the furanoside portion 17 proceed in 13 steps with 5% (from bisacetone-D-glucose), and in 12 steps with 7.6% over-all yield from dimethyl L-tartrate, respectively. (C) 2010 Elsevier Ltd. All rights reserved.