(1R)-1-[(3aR,5R,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]prop-2-en-1-ol | 106221-07-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R)-1-[(3aR,5R,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]prop-2-en-1-ol
• CAS: 106221-07-2
• 化学式: C₁₇H₂₂O₅
• 分子量: 306.359
• InChiKey: SBMVXWWAOMFYLX-IBEHDNSVSA-N

物化性质

• 沸点：
  412.4±45.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R)-1-[(3aR,5R,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]prop-2-en-1-ol 生成 3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose diacetate
  参考文献：
  名称：

  On the communication of chirality from furanose and pyranose rings to monosaccharide side chains: anomalous results in the glucose series

  摘要：

  DOI：

  10.1016/s0040-4020(01)90570-8
• 作为产物：
  描述：

  [(Z)-3-[(3aR,5R,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]prop-2-enyl]-trimethylsilane 在 三氟化硼乙醚 四氧化锇 作用下， 生成 (1R)-1-[(3aR,5R,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]prop-2-en-1-ol
  参考文献：
  名称：

  On the communication of chirality from furanose and pyranose rings to monosaccharide side chains: anomalous results in the glucose series

  摘要：

  DOI：

  10.1016/s0040-4020(01)90570-8

文献信息

• A straightforward approach towards glycoamino acids and glycopeptidesviaPd-catalysed allylic alkylation
  作者：Katja Krämer、Jan Deska、Christina Hebach、Uli Kazmaier

  DOI：10.1039/b813978d

  日期：——

  Chelated enolates are versatile nucleophiles for palladium-catalysed allylic alkylations. Even with complex allylic substrates the reaction proceed without significant isomerisation. This allows the stereoselective introduction of polyhydroxylated allylic sidechains into amino acids and peptides with retention of the olefin geometry.

  螯合的烯醇盐是用于钯催化的烯丙基烷基化反应的通用亲核试剂。即使使用复杂的烯丙基底物，反应也可以进行，而无需明显的异构化。这允许将多羟基化的烯丙基侧链立体选择性地引入氨基酸和肽中，并保留了烯烃的几何形状。
• Alternative Reagents for the Tritylation of Alcohols
  作者：Y. Jyothi、A. K. Mahalingam、A. Ilangovan、G. V. M. Sharma

  DOI：10.1080/00397910701357833

  日期：2007.6

  Abstract Two new tritylation reagents [viz. p‐methoxybenzyl trityl ether (p‐MBTE) and prenyl trityl ether (PTE)] were prepared. These two new reagents were utilized efficiently for the tritylation of alcohols, using DDQ or 20 mol% DDQ–3 eq. Mn(OAc)3.

  摘要 两种新的三苯甲基化试剂 [即。制备了对甲氧基苄基三苯甲基醚（p-MBTE）和异戊二烯基三苯甲基醚（PTE）]。这两种新试剂有效地用于醇的三苯甲基化，使用 DDQ 或 20 mol% DDQ–3 eq。Mn(OAc)3。
• A Facile Conversion of Alcohols into <i>p</i>-Methoxybenzyl Ethers (PMB-ethers) Using <i>p</i>-Methoxybenzyl Alcohol−Yb(OTf)₃
  作者：Sharma、Mahalingam

  DOI：10.1021/jo990563x

  日期：1999.11.1
• Sharma; Mahalingam; Prasad, Synlett, 2000, # 10, p. 1479 - 1481
  作者：Sharma、Mahalingam、Prasad

  DOI：——

  日期：——
• A practical one-pot radical-ionic sequence for the preparation of epoxides: application to the synthesis of unnatural polyhydroxylated alkaloids
  作者：Eduardo Peralta-Hernández、Omar Cortezano-Arellano、Alejandro Cordero-Vargas

  DOI：10.1016/j.tetlet.2011.10.042

  日期：2011.12

  An efficient one-pot sequence for the preparation of epoxides from alpha-iodoesters or alpha-iodonitriles and allylic alcohols is described. This sequence is based on the use of iodine atom transfer reaction onto allylic alcohols followed by a ring closing epoxidation reaction of the halohydrin intermediates. The feasibility of this sequence is showcased in the synthesis of the perhydroaza-azulene, an unnatural analog of castanospermine. (C) 2011 Elsevier Ltd. All rights reserved.