ethyl (5Z)-3-O-Benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-6-enofuranuroate | 108788-48-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl (5Z)-3-O-Benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-6-enofuranuroate
• 英文别名: ethyl (Z)-[3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]-heptofuran-5-en-uronate；ethyl 3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-5-eno-heptofuranuranoate；ethyl (Z)-3-(6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)acrylate；ethyl (Z)-3-[(3aR,5R,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]prop-2-enoate
• CAS: 108788-48-3
• 化学式: C₁₉H₂₄O₆
• 分子量: 348.396
• InChiKey: QKUAHWSYIPGNSW-YAAHHVHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl (5Z)-3-O-Benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-6-enofuranuroate 在 二异丁基氢化铝 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 3.0h， 以88%的产率得到5(Z)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-5-enofuranose
  参考文献：
  名称：

  合成一种新的氨基酸抗生素奥昔汀及其三种立体异构体。

  摘要：

  Oxetin（1a）是一种独特的含氧杂环的抗生素，其三种立体异构体（1b、1c和1d）是通过利用高度区域和立体选择性环氧化开环反应从已知的醛（6）合成的。对这些氧杂环立体异构体的生物活性进行了比较。

  DOI：

  10.1248/cpb.34.3102
• 作为产物：
  描述：

  3-O-苄基-1,2-O-异亚丙基-Alpha-D-木质二醛糖 、 乙氧甲酰基亚甲基三苯基膦 以 甲醇 为溶剂， 反应 2.0h， 以80%的产率得到ethyl (5Z)-3-O-Benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-6-enofuranuroate
  参考文献：
  名称：

  Ethoxycarbonylmethylenetriphenylphosphorane in carbohydrate chemistry : an easy access to functionalised 2-deoxy-3,6-anhydrohexono-1,4-lactones

  摘要：

  2-Deoxy-3,6-anhydrohexono-1,4-lactones are obtained efficiently from aldehydosugars in a two-step sequence involving a Wittig followed by acid-catalysed methanolysis.

  DOI：

  10.1016/0040-4039(91)80139-w

文献信息

• Wittig-Type Olefination Catalyzed by PEG-telluride
  作者：Zheng-Zheng Huang、Song Ye、Wei Xia、Yi-Hua Yu、Yong Tang

  DOI：10.1021/jo025586h

  日期：2002.5.1

  Soluble poly(ethylene glycol) (PEG)-supported telluride 2 was designed and synthesized for catalytic Wittig-type reactions. It was found that the catalytic loading could be reduced from 20 to 2 mol % by the introduction of PEG (even to 0.5 mol % when some telluride salts were used as the catalyst). Under the catalytic reaction conditions, a wide variety of aldehydes with different structures could

  设计并合成了可溶的聚乙二醇（PEG）负载的碲化物2，用于催化Wittig型反应。发现通过引入PEG可以将催化负载量从20mol％降低至2mol％（当使用一些碲化物盐作为催化剂时甚至可以降低至0.5mol％）。在催化反应条件下，具有不同结构的多种醛可以与溴乙酸酯反应，以高收率和优异的E-立体选择性提供β-取代的或α，β-二取代的不饱和酯。通过使用亚硫酸氢钠代替亚磷酸三苯酯的改进方法代表了非常简单的产物分离程序。公开了PEG在促进叶立德形成和稳定催化物质中的作用。还研究了该机制。
• Intermolecular Michael Addition of Substituted Amines to a Sugar-Derived α,β-Unsaturated Ester:  Synthesis of 1-Deoxy-<scp>d</scp>-<i>g</i><i>luco</i>- and -<scp>l</scp>-<i>i</i><i>do</i>-homonojirimycin, 1-Deoxy-castanospermine and 1-Deoxy-8a-<i>epi</i>-castanospermine
  作者：Nitin T. Patil、Jayant N. Tilekar、Dilip D. Dhavale

  DOI：10.1021/jo0010476

  日期：2001.2.1

  The synthesis of polyhydroxylated piperidine alkaloids, namely, 1-deoxy-D-gluco-homonojirimycin 3a, 1-deoxy-L-ido-homonojirimycin 3b, and indolizidine alkaloids 1-deoxy-castanospermine 5a and 1-deoxy-8a-epi-castanospermine 5b, has been achieved. The key step involved is the intermolecular Michael addition of benzylamine to alpha,beta-unsaturated ester 1, derived from D-glucose, which afforded diastereomeric

  多羟基化哌啶生物碱的合成，即1-脱氧-D-葡萄糖-homonojirimycin 3a，1-deoxy-L-ido-homonojirimycin 3b和吲哚并立生物碱1-deoxy-castanospermine 5a和1-deoxy-8a-ep-castanospermine 5b，已经实现。涉及的关键步骤是将分子胺在分子间的Michael加成反应中衍生自D-葡萄糖的α，β-不饱和酯1，从而得到β-氨基酯6a和6b的非对映异构体混合物，其中D-葡萄糖和L-ido-构型为C5分别。尝试增加和/或改变新生成的立体中心的非对映选择性。通过使用N-苄基氨基化锂作为迈克尔供体，在动力学控制的条件下实现了有利于L-偶合异构体6b的高立体选择性。β-氨基酯6a和6b代表目标分子的常见中间体。因此，LAH分别减少6a和6b，得到β-氨基醇7a和7b。依次氢解，氨基的选择性保护，然后水解1，2-丙酮化物
• Synthesis of five and six membered aminocyclitols: stereoselective Michael and Henry reaction approach with d-glucose derived α,β-unsaturated ester
  作者：Chaitali Chakraborty、Vinod P. Vyavahare、Vedavati G. Puranik、Dilip D. Dhavale

  DOI：10.1016/j.tet.2008.07.049

  日期：2008.9

  The stereoselective intermolecular Michael addition of nitromethane to d-glucose derived α,β-unsaturated ester 7 afforded l-ido-configurated nitroester 8 as the only product that on reduction of the ester functionality, cleavage of 1,2-acetonide and the intramolecular Henry reaction afforded exclusively muco-nitroinositol 9. While reduction of the ester functionality in 8, deprotection of 1,2-acetonide

  将硝基甲烷立体选择性地分子间迈克尔加成到d-葡萄糖衍生的α，β-不饱和酯7中，得到了l-氨基构型的硝酸酯8，这是唯一的酯官能度降低，1,2-丙酮化物裂解和分子内亨利分解的产物。反应，得到只粘膜-nitroinositol 9。虽然减少了8中的酯官能度，1,2-丙酮化物的脱保护，NaIO 4的氧化裂解和分子内的亨利反应提供了硝基环戊醇13。硝基环醇9和13分别转化为羟乙基取代的氨基环己糖醇5和氨基环戊糖醇6。
• Intramolecular Michael addition of benzylamine to sugar derived α,β-unsaturated ester: a new diastereoselective synthesis of a higher homologue of 1-deoxy-L-ido-nojirimycin
  作者：Vijaya N. Desai、Nabendu N. Saha、Dilip D. Dhavale

  DOI：10.1039/a905440e

  日期：——

  The diastereoselective intramolecular Michael addition of the benzylamine generated in situ from hemiacetal 3 leads to the lactone 4a with the required homoazasugar ring skeleton; reduction of the lactone functionality and removal of the protecting groups afford 1-deoxy-L-ido-homonojirimycin.

  半缩醛3在原位生成的苄胺的分子内迈克尔加成反应，生成具有所需同型氮杂糖环骨架的内酯4a；还原内酯官能团并去除保护基团，得到1-脱氧-L-异脱氧-同型诺吉里霉素。
• Synthesis of glycosylated β-amino acids as new class of antitubercular agents
  作者：R.P. Tripathi、R. Tripathi、V.K. Tiwari、Laxmi Bala、S Sinha、A. Srivastava、R. Srivastava、B.S. Srivastava

  DOI：10.1016/s0223-5234(02)01398-3

  日期：2002.9

  A series of glycosylated P-amino acids was prepared and evaluated against Mycohacterium tuberculosis, M. avium, M. fortuitum and M. smegmatis. The compounds were designed to mimic the enzyme D-alanine racemase and glycosyl transferase involved in the biosynthesis of essential cell wall peptidoglycan and arabinogalactan. Though most of the compounds exhibited little activity, however, one showed significant activity against all the strains in cell culture and activity was confirmed by BACTEC method. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.