(4R^*,5R^*)-2,2-dimethyl-5-n-pentyl-1,3-dioxolane-4-carboxaldehyde | 116949-69-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R^*,5R^*)-2,2-dimethyl-5-n-pentyl-1,3-dioxolane-4-carboxaldehyde
• 英文别名: (4R,5R)-2,2-dimethyl-5-pentyl-1,3-dioxolane-4-carbaldehyde
• CAS: 116949-69-0
• 化学式: C₁₁H₂₀O₃
• 分子量: 200.278
• InChiKey: YSLKOEAOCUWVEB-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R^*,5R^*)-2,2-dimethyl-5-n-pentyl-1,3-dioxolane-4-carboxaldehyde 在 palladium on activated charcoal 氢气 、 对甲苯磺酸 作用下， 以 甲醇 、 乙醇 、 正己烷 、 甲苯 为溶剂， 反应 12.0h， 生成 rac-L-因子
  参考文献：
  名称：

  化学酶法合成（4 S，5 R）-5-羟基-γ-癸内酯1

  摘要：

  用固定化的贝克酵母在pH 4.0下还原2-羟基-3-氧辛酸乙酯可产生具有高非对映选择性和对映选择性（de 70％，ee 80％）的抗-2 R，3 R-二羟基酯，可方便地转化为（4 S，5 R）-5-羟基-γ-癸内酯。

  DOI：

  10.1016/s0957-4166(99)00411-5
• 作为产物：
  描述：

  2-辛炔酸 在 Lindlar's catalyst 喹啉 、 四氧化锇 、 氢气 、 二异丁基氢化铝 、 对甲苯磺酸 、 N-甲基吗啉氧化物 作用下， 以 乙醚 、 正己烷 、 水 、 乙酸乙酯 、 丙酮 、 叔丁醇 为溶剂， -78.0~25.0 ℃ 、101.33 kPa 条件下， 反应 2.5h， 生成 (4R^*,5R^*)-2,2-dimethyl-5-n-pentyl-1,3-dioxolane-4-carboxaldehyde
  参考文献：
  名称：

  Synthesis of the cannabisativine skeleton via an intramolecular allylsilane-nitrone cycloaddition

  摘要：

  DOI：

  10.1021/jo00261a001

文献信息

• First stereoselective total synthesis and anticancer activity of new amide alkaloids of roots of pepper
  作者：Ch. Srinivas、Ch.N.S. Sai Pavan Kumar、B. China Raju、V. Jayathirtha Rao、V.G.M. Naidu、S. Ramakrishna、Prakash V. Diwan

  DOI：10.1016/j.bmcl.2009.08.056

  日期：2009.10

  The first stereoselective total synthesis of new natural amide alkaloids 1–3 have been achieved from commercially available starting materials. Wittig olefination, Sharpless asymmetric dihydroxylation, epoxidation, a trans regioselective opening of 2,3-epoxy alcohol, Horner–Wadsworth–Emmons (HWE) olefination and amide coupling are the key steps. The amide alkaloids 1–3 are evaluated for their anticancer

  的新的天然酰胺生物碱第一立体选择性全合成1 - 3已经从可商购的起始材料来实现的。Wittig烯烃化，Sharpless不对称二羟基化，环氧化，2,3-环氧醇的反式区域选择性开放，Horner-Wadsworth-Emmons（HWE）烯烃化和酰胺偶联是关键步骤。酰胺生物碱1 - 3用于抗结肠癌的人癌细胞系首次其抗癌活性（HT-29），乳腺癌（MCF-7）和肺（A-549）进行评价。
• Synthesis of all four isomers of (E)-4,5-dihydroxydec-2-enal using osmium-catalysed asymmetric dihydroxylation
  作者：Pietro Allevi、Giorgio Tarocco、Alessandra Longo、Mario Anastasia、Francesco Cajone

  DOI：10.1016/s0957-4166(97)00125-0

  日期：1997.4

  The enantioselective synthesis of the four possible isomers of (E)-4,5-dihydroxydec-2-enal, a cytotoxic product formed in peroxidised liver microsomal lipids, is accomplished via a Sharpless AD reaction alone or associated as appropriate with a regioselective epimerisation of one of the introduced hydroxy groups. (C) 1997 Elsevier Science Ltd.
• Synthesis and biological evaluation of truncated α-galactosylceramide derivatives focusing on cytokine induction profile
  作者：Tetsuya Toba、Kenji Murata、Junko Futamura、Kyoko Nakanishi、Bitoku Takahashi、Naohiro Takemoto、Minako Tomino、Takashi Nakatsuka、Seiichi Imajo、Megumi Goto、Takashi Yamamura、Sachiko Miyake、Hirokazu Annoura

  DOI：10.1016/j.bmc.2012.03.025

  日期：2012.5

  A series of truncated analogs of alpha-galactosylceramide with altered ceramide moiety was prepared, and evaluated for Th2-biased response in the context of IL-4/IFN-gamma ratio. Phytosphingosine-modified analogs including cyclic, aromatic and ethereal compounds as well as the C-glycoside analog of OCH (2) with their cytokine inducing profile are disclosed. (C) 2012 Elsevier Ltd. All rights reserved.
• The first synthesis of all possible stereoisomers of the (E)-4,5-dihydroxydec-2-enal, in homochiral form
  作者：Pietro Allevi、Pierangela Ciuffreda、Giorgio Tarocco、Mario Anastasia

  DOI：10.1016/0957-4166(95)00312-d

  日期：1995.9

  The first synthesis of the four possible isomers of (E)-4,5-dihydroxydec-2-enal, a cytotoxic product of microsomal lipid peroxidation, is accomplished starting with D- and L-arabinose, D-ribose and D-lyxose by an identical reaction sequence. Each pentose was diacetonised and subjected to a Wittig reaction for the introduction of a four carbon chain. A selective cleavage of the terminal isopropylidene acetal and the oxidation of the diolic system affords a noraldehyde which is treated with (formylmethylene)triphenylphosphorane to afford the target molecule after regeneration of the diolic system.
• A concise synthesis of (3S,4S,5R)-1-(α-d-galactopyranosyl)-3-tetracosanoylamino-4,5-decanediol, a C-glycoside analogue of immunomodulating α-galactosylceramide OCH
  作者：Tetsuya Toba、Kenji Murata、Takashi Yamamura、Sachiko Miyake、Hirokazu Annoura

  DOI：10.1016/j.tetlet.2005.05.069

  日期：2005.7

  A concise and convergent synthesis of the C-glycoside analogue 2b of immunomodulating alpha-galactosylceramide OCH 1b starting from readily available 2,3,4,6-tetra-O-bensyl-D-galactose 3 and L-arabinose 6 is described. The synthesis features the nucleophilic addition of an alpha-ethynyl sugar 5 to the phytosphingosine-precursor aldehyde 9 and would be applicable to a variety of C-glycoside analogues of interest. (c) 2005 Elsevier Ltd. All rights reserved.