3-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-α-D-xylo-furanuroic acid | 912942-92-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-α-D-xylo-furanuroic acid
• CAS: 912942-92-8
• 化学式: C₁₄H₂₆O₆Si
• 分子量: 318.442
• InChiKey: XEMZOCVYHHNWHF-UXCLJVHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.34
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  74.22
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-α-D-xylo-furanuroic acid 在 4-二甲氨基吡啶 、 tris-(dibenzylideneacetone)dipalladium(0) 、 噻吩-2-甲酸亚铜(I) 、 N,N'-二环己基碳二亚胺 、 亚磷酸三乙酯 作用下， 以 四氢呋喃 为溶剂， 生成 ((3aR,5S,6R,6aR)-6-((tert-butyldimethylsilyl)oxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl) (furan-2-yl)methanone
  参考文献：
  名称：

  Synthesis of (non-classical) C-acyl-glycosides via Liebeskind–Srogl coupling: Scope, limitation, improved synthesis and antioxidant activity of scleropentaside A

  摘要：

  DOI：

  10.1016/j.tet.2021.132255
• 作为产物：
  描述：

  3-O-[(t-butyl)dimethylsilyl]-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 在 chromium(VI) oxide 、 sodium periodate 、 硫酸 、 溶剂黄146 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 48.0h， 生成 3-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-α-D-xylo-furanuroic acid
  参考文献：
  名称：

  Diastereoselective syntheses of 1-deoxyhomonojirimycin and two new 1,5,6-trideoxy-1,5-iminoheptitols with d-allo- and l-talo-configuration

  摘要：

  The synthesis of 1-deoxyhomonojirimycin 2, as well as two new diastereomers, namely 1,5,6-trideoxy-1,5-imino-D-allo-heptitol 3 and 1,5,6-trideoxy-1,5-imino-L-talo-heptitol 4, is described. Compound 2 was obtained from 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose-while 3 and 4 were obtained from 1, 2:5,6-di-O-isopropylidene-alpha-D-allofuranose. These compounds were transformed in a few steps to the corresponding beta-ketoesters 12 and 18, respectively, which were hydrogenated diastereoselectively in the presence of chiral ruthenium complexes with total control of the C-5 stereogenic centre. The resulting beta-hydroxyesters 13, 19a and 19b are key intermediates for the syntheses of the 1,5,6-trideoxy-1,5-iminoheptitols 2, 3 and 4, respectively. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.07.022

文献信息

• Radical Decarboxylative Cyanomethylation of Aliphatic Carboxylic Acids and Uronic Acids via Vinyl Azide Cascade Fragmentation
  作者：Linhua Xu、Qishuai Li、Dongwei Li、Xin Zhou、Ni Song、Peng Wang、Ming Li

  DOI：10.1002/cjoc.202200732

  日期：——

  A direct oxidative radical decarboxylative cyanomethylation of carboxylic acids is described using 3-azido-2-methylbut-3-en-2-ol as the carbon-centered radical acceptor. The transformation is applicable to structurally diverse α-amino acids, α-oxy acids, α-keto acids, pentofuranuronic acids, and hexopyranuronic acids. The mechanistic investigations suggest that a radical process is involved in the

  使用 3-azido-2-methylbut-3-en-2-ol 作为以碳为中心的自由基受体，描述了羧酸的直接氧化自由基脱羧氰甲基化。该转化适用于结构多样的α-氨基酸、α-含氧酸、α-酮酸、戊呋喃糖醛酸和己吡喃糖醛酸。机械研究表明，转变涉及一个激进的过程。这项工作为构建具有生物学相关性的β-氨基酸、5-脱氧-己呋喃糖和 6-脱氧-庚糖提供了一种潜在的方法。