Ethyl 4,5-O-isopropylidene-(S)-4,5-dihydroxypentanoate | 36326-39-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Ethyl 4,5-O-isopropylidene-(S)-4,5-dihydroxypentanoate
• 英文别名: ethyl O-isopropylidene-(S)-4,5-dihydroxypentanoate；ethyl (4S)-4,5-(isopropylidenedioxy)-1-pentanoate；ethyl (4S)-4,5-(isopropylidenedioxy)pentanoate；ethyl (S)-4,5-isopropylidenedioxypentanoate；ethyl (S)-4,5-isopropanedioxypentanoate；ethyl (4S)-4,5-isopropylidenedioxy-1-pentanoate；Ethyl (4S)-2,2-dimethyl-1,3-dioxolane-4-propanoate；ethyl 3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]propanoate
• CAS: 36326-39-3
• 化学式: C₁₀H₁₈O₄
• 分子量: 202.251
• InChiKey: HCMXWEORDAJDFR-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Ethyl 4,5-O-isopropylidene-(S)-4,5-dihydroxypentanoate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以80%的产率得到3-[(4S)-2,2-二甲基-1,3-二氧戊烷-4-基]-丙醇
  参考文献：
  名称：

  针对clonostachydiol的合成的研究-第一部分

  摘要：

  已开发了用于氯硝水苏糖醇的首次总合成的策略，该策略随后将基于碳水化合物的手性合成子，基于卡隆方法确定绝对构型。然而，该研究最终达到了氯水苏糖醇的（2R，3R，8R，11S）异构体的合成。

  DOI：

  10.1016/0040-4039(94)02195-h
• 作为产物：
  描述：

  ethyl (Z)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate 在 platinum(IV) oxide 氢气 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、275.79 kPa 条件下， 反应 4.0h， 以99%的产率得到Ethyl 4,5-O-isopropylidene-(S)-4,5-dihydroxypentanoate
  参考文献：
  名称：

  Stereoselective synthesis of chiral tetrahydrofurans with potent 5-LO inhibitory activity

  摘要：

  Chiral glyceraldehydes have been exploited for the design of convenient and scalable synthetic approaches to chiral tetrahydrofurans, which have potential as potent 5-lipoxygenase (5-LO) inhibitors. The synthesis of all four possible stereoisomers by a general methodology is reported; wherein the chirons derived from the glyceraldehyde derivatives on reaction with homopropargyl ether, cyclization and further reactions gave the targets. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.01.045

文献信息

• Stereoselective Synthesis of (+)-SCH 351448:  A Unique Ligand System for Sodium, Calcium, and Other Cations
  作者：Eun Joo Kang、Eun Jin Cho、Mi Kyung Ji、Young Eun Lee、Dong Mok Shin、Soo Young Choi、Young Keun Chung、Jong-Seo Kim、Hie-Joon Kim、Sueg-Geun Lee、Myoung Soo Lah、Eun Lee

  DOI：10.1021/jo0507993

  日期：2005.8.1

  (+)-SCH 351448 (Na+ salt A) was synthesized employing ring-closing olefin metathesis reaction of an open diene diester intermediate for construction of the 28-membered macrodiolide structure. The open diene diester was prepared from the monomeric hydroxy carboxylic acid and two different olefin fragments. The monomeric hydroxy acid was synthesized via Julia-Julia coupling reaction of intermediates derived from the same olefinic fragments. Oxane units in these fragments were prepared by radical cyclization reactions of beta-alkoxyacrylates. Analogous SCH 351448 salts incorporating other mono- and divalent cations may be prepared. Under acidic conditions, SCH 351448 (Na+ salt A) was the most stable complex, but SCH 351448 (Ca2+ salt) and (Na+ salt B) appear to be physiologically important species.

  (+)−SCH 351448(钠盐A)是通过环闭烯烃复分解反应，利用一种开放性二烯二酯中间体构建28元大环二酯结构而合成的。该开放性二烯二酯是通过单体羟基羧酸和两种不同的烯烃片段制备的。单体羟基酸是通过Julia–Julia偶联反应，由同一烯烃片段衍生的中间体合成的。这些片段中的环氧丙烷单元是通过β−烷氧基丙烯酸酯的自由基环化反应制备的。类似地，SCH 351448盐中还可以引入其他单价和二价阳离子。在酸性条件下，SCH 351448(钠盐A)是最稳定的复合物，但SCH 351448(钙盐)和(钠盐B)似乎是有生理意义的物种。
• Methods for synthesis of substituted tetrahydrofuran compound
  申请人：Millennium Pharmaceuticals, Inc.

  公开号：US06310221B1

  公开（公告）日：2001-10-30

  The invention includes inter alia new methods for preparation of the pharmaceutically active compound 2-(4-fluorophenoxymethyl)-5-(4-N-hydroxyureidyl-1-butynyl)-tetrahydrofuran and precursors thereof.

  这项发明包括制备药用活性化合物2-(4-氟苯氧甲基)-5-(4-N-羟基脲基-1-丁炔基)-四氢呋喃及其前体的新方法，等等。
• Practical Synthesis of Some Versatile Chiral Building Blocks from (D)-Mannitol
  作者：Seiichi Takano、Ayako Kurotaki、Michiyasu Takahashi、Kunio Ogasawara

  DOI：10.1055/s-1986-31653

  日期：——

  The three chiral building blocks ethyl 4,5-O-isopropylidene-(E)-(S)-4, 5-dihydroxy-2-pentenoate [1,3-dioxolane derivative (E)-(S)-1a], (S)-5-hydroxy-4-pentanolide [(S)-2a], and (S)-5-hydroxy-2-penten-4-olide [(S)-3a] are conveniently prepared from 1,2;5,6-di-O-isopropylidene-D-mannitol (4) via a glycol cleavage and Horner-Emmons reaction sequence.

  这三种手性构建块，乙基4,5-O-异丙烯基-(E)-(S)-4,5-二羟基-2-戊烯酸酯 [1,3-二氧杂烷衍生物 (E)-(S)-1a]、(S)-5-羟基-4-戊内酯 [(S)-2a] 和(S)-5-羟基-2-戊烯-4-内酯 [(S)-3a]，通过甘油裂解和霍纳-埃蒙斯反应序列，从1,2;5,6-二-O-异丙烯基-D-甘露醇 (4) 方便地制备而成。
• Synthesis of (R)-(+)-Tanikolide through Stereospecific C-H Insertion Reaction of Dichlorocarbene with Optically Active Secondary Alcohol Derivatives
  作者：Hideki Arasaki、Masashi Iwata、Miyuki Makida、Yukio Masaki

  DOI：10.1248/cpb.52.848

  日期：——

  1,2-glycols, (S)-1,2-isopropylidenedioxytridecane (3) and ethyl (S)-4,5-isopropylidenedioxy-pentanoate (4), prepared from (R)-glyceraldehyde acetonide (2), with dichlorocarbene generated from CHCl(3)/50% NaOH/cetyltrimethylammonium chloride (as ptc.) took place with complete retention of configuration to provide (S)-4-dichloromethyl-2,2-dimethyl-4-undecyl-1,3-dioxolane (5) and ethyl (S)-3-(4-dichloromethyl-2

  由（R）-甘油醛制得的受保护的手性1,2-乙二醇，（S）-1,2-异丙基二烯二氧基十三烷（3）和（S）-4,5-异丙基二烯基戊氧基乙酯（4）的立体特异性αCH插入反应与CHCl（3）/ 50％NaOH /鲸蜡基三甲基氯化铵（如ptc。）生成的二氯卡宾进行乙炔化物（2）的构型完全保留，以提供（S）-4-二氯甲基-2,2-二甲基-4-十一烷基-1，3-二氧戊环（5）和（S）-3-（4-二氯甲基-2，2-二甲基-1，3-二氧戊环-4-基）-丙酸酯（8）。酯（8）通过侧链的延长转化为5。将二醇衍生物（5）转化为O-TBDPS保护的（S）-2-羟甲基-2-十一烷基环氧乙烷（16）。
• Stereoselective syntheses of pharmaceutically relevant chiral tetrahydrofurans from (S)- and (R)-glyceraldehyde derivatives
  作者：G.V.M. Sharma、Sreenivas Punna、T. Rajendra Prasad、Palakodety Radha Krishna、Mukund S. Chorghade、Steven V. Ley

  DOI：10.1016/j.tetasy.2005.01.044

  日期：2005.3

  A practically simple and flexible method of making chiral tetrahydrofurans of therapeutic relevance is reported from glyceraldehyde derivatives as chiral synthons. One of the stereocentres is derived from glyceraldehyde derivatives, while the other one is introduced by Sharpless asymmetric epoxidation using either (+)- or (−)-DIPT.

  从甘油醛衍生物作为手性合成子报道了一种制备具有治疗意义的手性四氢呋喃的实用简单且灵活的方法。一种立体中心衍生自甘油醛衍生物，而另一种立体中心通过使用（+）-或（-）-DIPT的Sharpless不对称环氧化引入。