(S)-3-(tert-butoxycarbonyl)-4-(1-oxo-hexadec-2-enyl)-2,2-dimethyloxazolidine | 129293-64-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (S)-3-(tert-butoxycarbonyl)-4-(1-oxo-hexadec-2-enyl)-2,2-dimethyloxazolidine
• 英文别名: (S,E)-tert-butyl 4-(hexadec-2-enoyl)-2,2-dimethyloxazolidine-3-carboxylate；tert-butyl (S,E)-4-(hexadec-2-enoyl)-2,2-dimethyloxazolidine-3-carboxylate；tert-butyl (4S)-4-[(E)-hexadec-2-enoyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 129293-64-7
• 化学式: C₂₆H₄₇NO₄
• 分子量: 437.663
• InChiKey: NVIKYFACLLKVAC-PANRORFQSA-N

物化性质

• 沸点：
  520.3±50.0 °C(Predicted)
• 密度：
  0.967±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  31
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-3-(tert-butoxycarbonyl)-4-(1-oxo-hexadec-2-enyl)-2,2-dimethyloxazolidine 在 sodium tetrahydroborate 、 cerium(III) chloride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.08h， 生成 N-叔丁氧羰基-赤式-鞘氨醇
  参考文献：
  名称：

  A diversity oriented synthesis of d - erythro -sphingosine and siblings

  摘要：

  An efficient building block-based synthetic protocol has been developed for the synthesis of 3-keto-sphingoids with various chain lengths using cross metathesis of a Garner's aldehyde-derived alpha,beta-unsaturated ketone as the key step. Stereoselective reduction of the biomimetic precursors thus obtained provided D-elythro-sphingosine and truncated anaogues in good overall yields. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2017.08.006
• 作为产物：
  描述：

  十四醇 在 2,2,6,6-四甲基哌啶氧化物 、 三氯异氰尿酸 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 1.5h， 生成 (S)-3-(tert-butoxycarbonyl)-4-(1-oxo-hexadec-2-enyl)-2,2-dimethyloxazolidine
  参考文献：
  名称：

  US2014/275590

  摘要：

  公开号：

文献信息

• Chiral combinatorial preparation and biological evaluation of unique ceramides for inhibition of sphingomyelin synthase
  作者：Sajeer Koolath、Yuta Murai、Yoshiko Suga、Kenji Monde

  DOI：10.1002/chir.23179

  日期：2020.3

  Enantiomers or diastereomers of chiral bioactive compounds often exhibit different biological and toxicological properties. Here, we report the efficient synthesis of four stereoisomers of sphingosine and derivatization of unique chiral ceramides through a combinatorial chemistry by solid‐phase activated resin ester. In addition, to test the effectivity of stereochemistry of ceramide, we demonstrated

  手性生物活性化合物的对映异构体或非对映异构体通常表现出不同的生物学和毒理学性质。在这里，我们报告了鞘氨醇的四种立体异构体的有效合成，以及通过固相活化树脂酯的组合化学，将独特的手性神经酰胺衍生化。此外，为了测试神经酰胺的立体化学的有效性，我们证明了在手性独特神经酰胺存在下基于神经鞘磷脂合成酶抑制的细胞测定，这表明此类文库将是生物活性合成分子的丰富来源。
• Chemoenzymatic Total Synthesis of GM3 Gangliosides Containing Different Sialic Acid Forms and Various Fatty Acyl Chains
  作者：Hai Yu、Madhusudhan Reddy Gadi、Yuanyuan Bai、Libo Zhang、Lei Li、Jun Yin、Peng G. Wang、Xi Chen

  DOI：10.1021/acs.joc.1c00450

  日期：2021.7.2

  diverse GM3 gangliosides containing various sialic acid forms and different fatty acyl chains in low cost, an improved process was developed to chemically synthesize lactosyl sphingosine from an inexpensive l-serine derivative. It was then used to obtain GM3 sphingosines from diverse modified sialic acid precursors by an efficient one-pot multienzyme sialylation system containing Pasteurella multocida

  神经节苷脂是一种含唾液酸的鞘糖脂，已在所有脊椎动物的细胞膜中发现。它们的重要生物学功能由聚糖和神经酰胺脂质成分共同贡献。GM3 是一种主要的神经节苷脂，也是许多其他更复杂的神经节苷脂的前体。为了以低成本获得结构多样的含有各种唾液酸形式和不同脂肪酰基链的 GM3 神经节苷脂，开发了一种改进的工艺，以从廉价的l-丝氨酸衍生物化学合成乳糖基鞘氨醇。然后将其用于通过有效的一锅多酶唾液酸化系统从多种修饰的唾液酸前体中获得 GM3 鞘氨醇，该系统含有多杀性巴氏杆菌唾液酸转移酶 3 (PmST3 )糖核苷酸的产生。然后使用高效的化学酰化和简便的 C18 滤芯纯化工艺来安装不同长度和不同修饰的脂肪酰基链。化学酶法代表了一种强大的全合成策略，可以访问结构定义的 GM3 神经节苷脂库以探索其功能。
• METHODS FOR THE SYNTHESIS OF SPHINGOMYELINS AND DIHYDROSPHINGOMYELINS
  申请人：CERENIS THERAPEUTICS HOLDING SA

  公开号：US20140316154A1

  公开（公告）日：2014-10-23

  The present invention includes methods for the synthesis of sphingomyelins and dihydrosphingomyelins. The present invention also includes methods for the synthesis of sphingosines and dihydrosphingosines. The present invention further includes methods for the synthesis of ceramides and dihydroceramides.

  本发明涉及合成鞘磷脂和二氢鞘磷脂的方法。本发明还涉及合成鞘氨醇和二氢鞘氨醇的方法。本发明还涉及合成鞘醇和二氢鞘醇的方法。
• Selective deuterium labeling of the sphingoid backbone: facile syntheses of 3,4,5-trideuterio-d-erythro-sphingosine and 3-deuterio-d-erythro-sphingomyelin
  作者：Hoe-Sup Byun、Robert Bittman

  DOI：10.1016/j.chemphyslip.2010.09.001

  日期：2010.11

  Deuteration at C-4 and C-5 of sphingosine was achieved via a hydrogen-deuterium exchange reaction of a beta-ketophosphonate intermediate catalyzed by ND4Cl in D2O/tetrahydrofuran. To install deuterium at C-3 of sphingosine and sphingomyelin, sodium borodeuteride reduction/cerium(111) chloride reduction of an alpha,beta-enone in perdeuteromethanol was used. (c) 2010 Elsevier Ireland Ltd. All rights reserved.
• Synthesis of D-erythro-sphingosine and D-erythro-sphinganine via 3-ketosphinganine
  作者：Robert V. Hoffman、Junhua Tao

  DOI：10.1016/s0040-4039(98)00733-3

  日期：1998.6

  D-erythro-sphingosine and D-erythro-sphinganine can be produced in protected form from serine by a synthetic approach in which the normal biological intermediate 3-ketosphinganine in protectyed form, is a key synthetic intermediate. The sequence is short and convergent, proceeds in goad overall yields (approximate to 30% for 6 steps) and with excellent stereocontrol (>91% de, >95% ee). (C) 1998 Elsevier Science Ltd. All rights reserved.