tert-butyl (4S)-4-[(1R,2E)-1-hydroxy-3-phenyl-2-propenyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate | 154437-24-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: tert-butyl (4S)-4-[(1R,2E)-1-hydroxy-3-phenyl-2-propenyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• 英文别名: tert-butyl (4S)-4-[(1R,2E)-1-hydroxy-3-phenylprop-2-en-1-yl]-2,2-dimethyloxazolidine-3-carboxylate；tert-butyl (4S)-4-[(E,1R)-1-hydroxy-3-phenylprop-2-enyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 154437-24-8
• 化学式: C₁₉H₂₇NO₄
• 分子量: 333.428
• InChiKey: HTZJVRIZHJLLOH-HMUVLFPJSA-N

物化性质

• 沸点：
  464.6±40.0 °C(Predicted)
• 密度：
  1.117±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (4S)-4-[(1R,2E)-1-hydroxy-3-phenyl-2-propenyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 在 吡啶 、 三甲基溴硅烷 、 四溴化碳 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 Phosphoric acid mono-((E)-(2S,3R)-2-amino-3-hydroxy-5-phenyl-pent-4-enyl) ester
  参考文献：
  名称：

  Synthesis and biological properties of novel sphingosine derivatives

  摘要：

  Sphingosine-1-phosphate (S-1P) derivatives such as threo-(2S,3S)-analogues, which are C-3 stereoisomers of natural erythro-(2S,3R)-S-1P, have been synthesized starting from L-serine or (IS,2S)-2-amino-1-aryl-1,3-propanediols (6). threo-(IS,2R)2-Amino-1-aryl-3-bromopropanols (HBr salt) have also been prepared from 6. The threo-S-1Ps and the threo-amino-bromide derivatives have shown potent inhibitory activity against Ca2+ ion mobilization in HL60 cells induced by erythro-S-1P, suggesting that these compounds would compete with cell surface EDG/S1P receptors. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.010
• 作为产物：
  描述：

  3-反-溴碳-2,2'-二甲基氧酸酯 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 tert-butyl (4S)-4-[(1R,2E)-1-hydroxy-3-phenyl-2-propenyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
  参考文献：
  名称：

  通过交叉复分解反应高效合成（2S，3R，4E）-N2-十八碳酰基-4-十四碳黄嘌呤的苯乙烯基类似物

  摘要：

  鞘脂的第一全合成（2小号，3 - [R，4 ë） - ñ 2 -octadecanoyl -4- tetradecasphingenine（1A），天然鞘脂从虫语料库101A分离，并且它的苯乙烯基类似物的图1b是在良好的总收率达到（方案1和2）。关键步骤涉及通过交叉复分解反应（→ 5a或5b）在烯丙醇衍生物3上以（E）立体选择性安装长亲脂性链或苯基。受N‐ Boc保护的3 可以很容易地从（S）‐ Garner醛中获得。

  DOI：

  10.1002/hlca.201000277

文献信息

• Diastereoselective addition of alkenylchromium(III) reagents to Garner’s aldehyde: Nozaki-Hiyama-Kishi coupling approach to sphingosines and ceramides
  作者：Zorana Ferjancic、Radomir Matovic、Filip Bihelovic

  DOI：10.2298/jsc130611067f

  日期：——

  between alkenyl- chromium(III) reagents, derived from either (E)-(2-bromoethenyl)benzene or (E)-1-iodo-1-pentadecene, and the conformationally rigid Garner's aldehyde resulted in the stereoselective formation of Felkin-type allylic alcohols in good yields, thus providing an easy access to sphingosines. In addition, when the protecting group in the Garner's aldehyde was changed (from Boc to N-octa- noyl)

  （E）-（2-溴乙烯基）苯或（E）-1-碘-1-戊烯的烯基-铬（III）试剂与构象刚性的Garner醛之间的分子间Nozaki-Hiyama-Kishi偶联导致Felkin型烯丙基醇的立体选择性形成具有良好的收率，因此易于获得鞘氨醇。另外，当加纳醛中的保护基发生变化（从Boc变为N-辛基）时，在与（E）-1-戊烯基铬（III）的反应中观察到立体选择性的逆转。反应伙伴的长碳链之间的疏水作用的关系。
• Efficient stereodivergent synthesis of erythro- and threo-sphingosines: unprecedented reversal of the stereochemistry in the addition
  作者：Teiichi Murakami、Kiyotaka Furusawa

  DOI：10.1016/s0040-4020(02)01190-0

  日期：2002.11

  A convenient diastereoselective synthesis of d-erythro- and l-threo-sphingosine derivatives is described. l-Serine-derived aldehyde (Garner's aldehyde) (2) was treated with 1-alkenyl-zirconocene chlorides (3) in the presence of ZnBr2 in THF to give the natural erythro-(anti-) isomers with high diastereoselectivity (anti/syn=12–20:1). In contrast, reaction of 2 with 1-alkenyl-ethyl-zinc, prepared from

  的D-阿方便非对映选择性合成赤-和1-苏式-sphingosine衍生物进行说明。L-丝氨酸衍生的醛（加纳的醛）（2）与1-链烯基锆氯化物（处理3在ZnBr的存在下）2在THF中以得到天然赤- （反- ）具有高非对映选择性异构体（反/ syn = 12–20：1）。相反，2与由3和Et 2 Zn制备的1-烯基-乙基-锌在CH 2 Cl 2中的反应产生了不自然的苏氨酸-（syn-）异构体为主（anti / syn = 1：12-15）。
• Synthetic studies towards amino alcohols. Diastereocontrolled reduction of α′-chiral α,β-enones.
  作者：Ari M.P. Koskinen、Päivi M. Koskinen

  DOI：10.1016/s0040-4039(00)61696-9

  日期：1993.10

  A stereocontrolled route for alpha'-amino allylic alcohols has been realised using L-serine as starting material. The title compounds are versatile synthons in a variety of natural product syntheses.
• Synthesis and biological properties of novel sphingosine derivatives
  作者：Teiichi Murakami、Kiyotaka Furusawa、Tadakazu Tamai、Kazuyoshi Yoshikai、Masazumi Nishikawa

  DOI：10.1016/j.bmcl.2004.12.010

  日期：2005.2

  Sphingosine-1-phosphate (S-1P) derivatives such as threo-(2S,3S)-analogues, which are C-3 stereoisomers of natural erythro-(2S,3R)-S-1P, have been synthesized starting from L-serine or (IS,2S)-2-amino-1-aryl-1,3-propanediols (6). threo-(IS,2R)2-Amino-1-aryl-3-bromopropanols (HBr salt) have also been prepared from 6. The threo-S-1Ps and the threo-amino-bromide derivatives have shown potent inhibitory activity against Ca2+ ion mobilization in HL60 cells induced by erythro-S-1P, suggesting that these compounds would compete with cell surface EDG/S1P receptors. (C) 2004 Elsevier Ltd. All rights reserved.
• Efficient Synthesis of a Styryl Analogue of (2S,3R,4E)-N2-Octadecanoyl-4-tetradecasphingenine via Cross-Metathesis Reaction
  作者：Gulshan Kumar、Sukhbir Kaur、Vasundhara Singh

  DOI：10.1002/hlca.201000277

  日期：2011.4

  The first total synthesis of sphingolipid (2S,3R,4E)‐N2‐octadecanoyl‐4‐tetradecasphingenine (1a), a natural sphingolipid isolated from Bombycis Corpus 101A, and of its styryl analogue 1b was achieved in good overall yield (Schemes 1 and 2). The key step involved the installation with (E) stereoselectivity of a long lipophilic chain or phenyl group on allyl alcohol derivative 3 via a cross‐metathesis

  鞘脂的第一全合成（2小号，3 - [R，4 ë） - ñ 2 -octadecanoyl -4- tetradecasphingenine（1A），天然鞘脂从虫语料库101A分离，并且它的苯乙烯基类似物的图1b是在良好的总收率达到（方案1和2）。关键步骤涉及通过交叉复分解反应（→ 5a或5b）在烯丙醇衍生物3上以（E）立体选择性安装长亲脂性链或苯基。受N‐ Boc保护的3 可以很容易地从（S）‐ Garner醛中获得。