(1R,2R,3S,4R,5R)-5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-propenyloxy-tetrahydro-furo[2,3-d][1,3]dioxole | 142435-23-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2R,3S,4R,5R)-5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-propenyloxy-tetrahydro-furo[2,3-d][1,3]dioxole
• 英文别名: (3aR,5R,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6-[(E)-prop-1-enoxy]-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
• CAS: 142435-23-2
• 化学式: C₁₅H₂₄O₆
• 分子量: 300.352
• InChiKey: RSCYQPRGEVQBEZ-LMJJHZHSSA-N

物化性质

• 沸点：
  371.2±42.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1R,2R,3S,4R,5R)-5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-propenyloxy-tetrahydro-furo[2,3-d][1,3]dioxole 在 四氧化锇 、 N-甲基吲哚酮 作用下， 以 丙酮 为溶剂， 反应 43.0h， 以82%的产率得到双丙酮葡萄糖
  参考文献：
  名称：

  Study of metal and acid catalysed deprotection of propargyl ethers of alcohols via their allenyl ethers

  摘要：

  A new method for the deprotection of prop-2-ynyl ethers 1b-9b is described. Isomerisation of 1b-9b to O-allenyl ethers 1d-9d and deprotection by reaction with Hg(OCOCF3)(2), aq.HCl, aq.CF3CO2H and best by use of a catalytic amount of OsO4 is described to obtain the alcohols 1a-9a in good yield. Application of this method for the deprotection of prop-2-enyl ethers 7c,8c,10c-13c via their corresponding prop-1-enyl ethers 7e,8e,10e-13e to obtain the corresponding alcohols 7a,8a,10a-13a is also described, (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00631-6
• 作为产物：
  描述：

  (3R,4S)-3-[(4R)-2,2-二甲基-1,3-二氧戊环-4-基]-7,7-二甲基-4-丙-2-烯氧基-2,6,8-三氧杂双环[3.3.0]辛烷 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 反应 8.0h， 以81%的产率得到(1R,2R,3S,4R,5R)-5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-propenyloxy-tetrahydro-furo[2,3-d][1,3]dioxole
  参考文献：
  名称：

  Study of metal and acid catalysed deprotection of propargyl ethers of alcohols via their allenyl ethers

  摘要：

  A new method for the deprotection of prop-2-ynyl ethers 1b-9b is described. Isomerisation of 1b-9b to O-allenyl ethers 1d-9d and deprotection by reaction with Hg(OCOCF3)(2), aq.HCl, aq.CF3CO2H and best by use of a catalytic amount of OsO4 is described to obtain the alcohols 1a-9a in good yield. Application of this method for the deprotection of prop-2-enyl ethers 7c,8c,10c-13c via their corresponding prop-1-enyl ethers 7e,8e,10e-13e to obtain the corresponding alcohols 7a,8a,10a-13a is also described, (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00631-6

文献信息

• Efficient Allyl to Propenyl Isomerization in Functionally Diverse Compounds with a Thermally Modified Grubbs Second-Generation Catalyst
  作者：Stephen Hanessian、Simon Giroux、Andreas Larsson

  DOI：10.1021/ol062167o

  日期：2006.11.1

  Heating compounds containing C-allylic appendages in MeOH in the presence of 10 mol % of Grubbs second-generation catalyst at 0.075 M substrate concentration leads to the corresponding 2-propenyl derivatives without further conjugation in the cases of ketones, esters, and lactams. The reaction is applicable to a large variety of functionally relevant terminal olefins, including O- and N-allyl ethers

  在10摩尔％的Grubbs第二代催化剂存在下，在0.075 M底物浓度下，在MeOH中加热包含C-烯丙​​基附件的化合物，在酮，酯和内酰胺的情况下，无需进一步偶联即可得到相应的2-丙烯基衍生物。该反应适用于多种功能相关的末端烯烃，包括O-和N-烯丙基醚。[反应：请参见文字]。
• A novel, mild palladium mediated deprotection of O-allyl and prop-1-enyl ethers
  作者：Hari Babu Mereyala、Sreenivasulu Guntha

  DOI：10.1016/s0040-4039(00)91833-1

  日期：1993.10

  A mild method for the deprotection of diverse 0-allyl (1a-5a) and prop-l-enyl ethers (1d-5d) of glycosides and inositol by use of PdCl2/CuCl/DMF-H2O/02 is described.
• Study of metal and acid catalysed deprotection of propargyl ethers of alcohols via their allenyl ethers
  作者：Hari Babu Mereyala、Srinivas Reddy Gurrala、S Krishna Mohan

  DOI：10.1016/s0040-4020(99)00631-6

  日期：1999.9

  A new method for the deprotection of prop-2-ynyl ethers 1b-9b is described. Isomerisation of 1b-9b to O-allenyl ethers 1d-9d and deprotection by reaction with Hg(OCOCF3)(2), aq.HCl, aq.CF3CO2H and best by use of a catalytic amount of OsO4 is described to obtain the alcohols 1a-9a in good yield. Application of this method for the deprotection of prop-2-enyl ethers 7c,8c,10c-13c via their corresponding prop-1-enyl ethers 7e,8e,10e-13e to obtain the corresponding alcohols 7a,8a,10a-13a is also described, (C) 1999 Elsevier Science Ltd. All rights reserved.