[(S)-1-((4S,5R)-2,2-Dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-allyl]-carbamic acid tert-butyl ester | 799267-96-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(S)-1-((4S,5R)-2,2-Dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-allyl]-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(1S)-1-[(4S,5R)-2,2-dimethyl-5-tetradecyl-1,3-dioxolan-4-yl]prop-2-enyl]carbamate
• CAS: 799267-96-2
• 化学式: C₂₇H₅₁NO₄
• 分子量: 453.706
• InChiKey: PACLPPPZYMNORV-VXNXHJTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  32
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(S)-1-((4S,5R)-2,2-Dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-allyl]-carbamic acid tert-butyl ester 在 PhCH=Ru[1,3-bis(2,4,6-Me₃C₆H₂)-2-imidazolidinylidene]Cl₂ 三乙基硅烷 、 4-二甲氨基吡啶 、 三氟乙酸 、 三环己基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 Acetic acid (2R,3S,4R,5S,6R)-3,5-diacetoxy-2-acetoxymethyl-6-((E)-(3S,4S,5R)-3-hexacosanoylamino-4,5-dihydroxy-nonadec-1-enyl)-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Efficient Synthesis of α-C-Galactosyl Ceramide Immunostimulants: Use of Ethylene-Promoted Olefin Cross-Metathesis

  摘要：

  Olefin cross-metathesis has been used to prepare alpha-C-galactosylceramide derivatives. The metathesis process merged vinyl and propenyl glycosides with vinyl derivatives of phytosphingosine. The use of ethylene enhanced the yield of the methathesis step.

  DOI：

  10.1021/ol0482137
• 作为产物：
  描述：

  糖脂 在 4-二甲氨基吡啶 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hydroxide 、 polymer-NMe₃*Br(OAc)2 、 四丁基氟化铵 、 4-甲基苯磺酸吡啶 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 6.5h， 生成 [(S)-1-((4S,5R)-2,2-Dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-allyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Efficient Synthesis of α-C-Galactosyl Ceramide Immunostimulants: Use of Ethylene-Promoted Olefin Cross-Metathesis

  摘要：

  Olefin cross-metathesis has been used to prepare alpha-C-galactosylceramide derivatives. The metathesis process merged vinyl and propenyl glycosides with vinyl derivatives of phytosphingosine. The use of ethylene enhanced the yield of the methathesis step.

  DOI：

  10.1021/ol0482137

文献信息

• Novel synthetic C-glycolipids, their synthesis and use to treat infections, cancer and autoimmune diseases
  申请人：Tsuji Moriya

  公开号：US20050222048A1

  公开（公告）日：2005-10-06

  The invention is directed to novel compounds of formulae (I), (II) and (III): wherein X is O or NH; R 3 is OH or a monosaccharide and R 4 is hydrogen, or R 3 is hydrogen and R 4 is OH or a monosaccharide; R 5 is hydrogen or a monosaccharide; and pharmaceutically acceptable salts or esters thereof. The invention is also directed to the use of the compounds both directly and as immune adjuvants for treating cancer, infectious diseases and autoimmune diseases. The invention is also directed to syntheses of the intermediates which can be used to make these novel compounds.

  该发明涉及以下化合物的新颖化合物：其中X为O或NH；R3为OH或单糖，R4为氢，或R3为氢，R4为OH或单糖；R5为氢或单糖；以及其药用盐或酯。该发明还涉及这些化合物的直接使用以及作为免疫佐剂用于治疗癌症、传染病和自身免疫疾病。该发明还涉及合成这些中间体的方法，这些中间体可用于制备这些新颖化合物。
• Synthesis of CH₂-linked α-galactosylceramide and its glucose analogues through glycosyl radical-mediated direct <i>C</i>-glycosylation
  作者：Yu Hidaka、Noriaki Kiya、Makoto Yoritate、Kazuteru Usui、Go Hirai

  DOI：10.1039/d0cc00785d

  日期：——

  Direct C-glycosylation of a conformationally constrained and stable C1-sp³ hybridized carbohydrate donor with a carefully designed sphingosine unit afforded the CH₂-linked analogue of antitumor-active KRN7000 and its glucose congener.

  将一个构象受限且稳定的C1-sp3杂化糖供体与精心设计的鞘氨醇单元直接C-糖基化，得到了与抗肿瘤活性KRN7000及其葡萄糖同源物相连的CH2-连接类似物。
• Efficient Synthesis of α-C-Galactosyl Ceramide Immunostimulants: Use of Ethylene-Promoted Olefin Cross-Metathesis
  作者：Guangwu Chen、John Schmieg、Moriya Tsuji、Richard W. Franck

  DOI：10.1021/ol0482137

  日期：2004.10.1

  Olefin cross-metathesis has been used to prepare alpha-C-galactosylceramide derivatives. The metathesis process merged vinyl and propenyl glycosides with vinyl derivatives of phytosphingosine. The use of ethylene enhanced the yield of the methathesis step.