ethyl (R)-2-(benzyloxy)-2-[(4'R)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]acetate | 287119-15-7

• 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 (R)-2-(benzyloxy)-2-[(4'R)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]acetate
• 英文别名: (R)-ethyl 2-(benzyloxy)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)acetate；(R)-ethyl 2-(benzyloxy)-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)acetate；ethyl (2R)-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-phenylmethoxyacetate
• CAS: 287119-15-7
• 化学式: C₁₆H₂₂O₅
• 分子量: 294.348
• InChiKey: KZWTUVGKJZXLIL-ZIAGYGMSSA-N

物化性质

• 沸点：
  400.6±35.0 °C(Predicted)
• 密度：
  1.111±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (R)-2-(benzyloxy)-2-[(4'R)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]acetate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以89%的产率得到1-O-benzyl-3,4-O-isopropylidene-D-erythritol (12) and 2-O-benzyl-3,4-O-isopropylidene-D-erythritol
  参考文献：
  名称：

  （+）-spisulosine的总合成及其抗癌活性

  摘要：

  已经完成了抗癌药（+）-spisulosine的全合成。该策略涉及底物控制的aza-Claisen重排以建立赤型构型的氨基醇基序，然后进行脱氧以创建甲基侧链。随后随后的维蒂希烯化反应允许构建靶分子的碳主链。为研究1的抗增殖作用，在一组6种人类恶性细胞系上检查了其生物学特性，并证明了1对至少5种评估系具有显着的抗癌活性，IC50 <1μM（MCF-7，HTC- 116，Caco-2，Jurkat和HeLa）。

  DOI：

  10.1016/j.carres.2016.09.010
• 作为产物：
  描述：

  ethyl (R)-2-[(4'R)-2',2'-dimethyl-1,3-dioxolan-4'-yl]-2-hydroxyacetate 、 溴甲苯 在 silver(l) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以87%的产率得到ethyl (R)-2-(benzyloxy)-2-[(4'R)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]acetate
  参考文献：
  名称：

  具有植物毒性的10元内酯标本I的新合成

  摘要：

  从12个步骤中，由d-（-）-异抗坏血酸合成了具有植物毒性的10元内酯的植物标本植物I，总收率为16.8％。产生C-8立体异构中心的方法学是Sharpless不对称环氧化，以及1,2-不对称诱导，然后通过RCM进行大内酯化。

  DOI：

  10.1016/j.tetasy.2009.03.034

文献信息

• SUBSTITUTED BIARYL ALKYL AMIDES
  申请人：BioTheryX, Inc.

  公开号：US20130102649A1

  公开（公告）日：2013-04-25

  Disclosed herein are substituted biaryl alkyl amide compounds, methods of synthesizing substituted biaryl alkyl amide compounds and methods of treating diseases and/or conditions with substituted biaryl alkyl amide compounds.

  本文披露了替代的联苯烷基酰胺化合物，合成替代的联苯烷基酰胺化合物的方法，以及利用替代的联苯烷基酰胺化合物治疗疾病和/或症状的方法。
• A new synthesis of the phytotoxic 10-membered lactone herbarumin I
  作者：J. Jon Paul Selvam、K. Rajesh、V. Suresh、D. Chanti Babu、Y. Venkateswarlu

  DOI：10.1016/j.tetasy.2009.03.034

  日期：2009.6

  Herbarumin I a phytotoxic 10-membered lactone has been synthesized from d-(−)-isoascorbic acid in 12 steps with an overall yield of 16.8%. The methodology involved in generating the stereogenic center at C-8 is a Sharpless asymmetric epoxidation, as well 1,2-asymmetric induction followed by macrolactonization via RCM.

  从12个步骤中，由d-（-）-异抗坏血酸合成了具有植物毒性的10元内酯的植物标本植物I，总收率为16.8％。产生C-8立体异构中心的方法学是Sharpless不对称环氧化，以及1,2-不对称诱导，然后通过RCM进行大内酯化。
• Enantioselective Synthesis of Ethyl 4,5,7,8,9-Penta-O-acetyl-2,6-anhydro- 3-deoxy-D-erythro-L-gluca-nononate: a 2-Monodeoxygenated Derivative of `2-Keto-3-deoxy-D-glycero-D-galacto-nononic Acid'
  作者：Xin Shen、Yu-Lin Wu、Yikang Wu

  DOI：10.1002/(sici)1522-2675(20000510)83:5<943::aid-hlca943>3.0.co;2-h

  日期：2000.5.10

  A study aimed at developing an enantioselective synthesis of the title compound 23, a 2-monodeoxy analogue of;he naturally occurring (+)-2-keto-3-deoxy-D-glycero-D-galacto-2-nononic acid (KDN),is reported. From D-mannose as starting material, the chiral 1,3-diene 10, activated by a silyloxy substituent at C(2), was prepared in six steps (Scheme I). However, the intermediates were often contaminated with varying amounts of by-products arising from overoxidation during cleavage with periodic acid. An alternative route starting from the inexpensive and readily available D-isoascorbic acid (12), though a little longer than the first, satisfactorily circumvented the purification problem and led to the desired dienes 17 in good yields (scheme2). The [Co-II(S.S)-(+)-salen]-catalyzed hetero-Diels-Alder reactions of the aforementioned dienes with ethyl glyoxylate proceeded smoothly at room temperature, giving the dihydropyrano adducts 18 in moderate yields (Scheme 3). Dihydroxylation of 18a followed by reduction of the keto function gave the desired 4,5-trans dihydroxy moiety of the KDN framework (Scheme 4, see 21). The spectroscopic data of the penta-O-acetylated 2-deoxy-KDN ethyl ester 23 were consistent with those reported for the corresponding methyl ester derived from natural KDN.
• Synthesis of Imidazolo-Piperidinopentoses as Nagstatine Analogues
  作者：François Gessier、Théophile Tschamber、Céline Tarnus、Markus Neuburger、Walter Huber、Jacques Streith

  DOI：10.1002/1099-0690(200111)2001:21<4111::aid-ejoc4111>3.0.co;2-7

  日期：2001.11

  The syntheses of the four imidazolo-piperidino-pentoses 3-6, which belong to the D-series, and of their L-enantiomers, ent-3 to ent-6, are reported. Ascorbic acid and isoascorbic acid were converted over several steps into the L-threo/L-erythro- and the D-erythro/D-threo-configured aldotetroses, respectively, which are the key building blocks for the eight target imidazolo-pentoses cited above. Nucleophilic addition of a metallated imidazole to any one of these four aldotetroses gave the corresponding two diastereomeric adducts, intramolecular cyclisation of which provided the expected bicyclic target molecules, with some protection and deprotection steps being unavoidable prerequisites. The structures and configurations of all eight piperidinoses in Scheme 1 were determined unambiguously, by a combination of H-1/C-13 NMR spectroscopy, circular dichroism (CD) and MD values, in conjunction with single-crystal X-ray diffraction analyses of the L-arabino and D-lyxo azasugars ent-3 and 6. Although lacking the hydroxymethylene group in the C(5) position, the overall structure of these eight stereomers strongly resembles that of the natural product nagstatine (1), a potent inhibitor of N-acetyl-beta -D-glucosaminidase. As a matter of fact, after examination of the inhibitory properties of these imidazolo-piperidinoses against six commonly encountered glycosidases, we observe that the L-arabino imidazolo-sugar ent-3 is a potent inhibitor in this series, with K-i = 1 muM both with a beta -glucosidase and with a beta -galactosidase. The D-ribo and D-xylo stereomers 4 and 5 proved to be inhibitors of a beta -glucosidase of similar magnitude (4: K-i = 20 muM; 5: K-i = 17 muM), the other stereomers being either modest to poor inhibitors, or showing no inhibition at all.
• The formal synthesis of 3-epi jaspine B using stereoselective intramolecular oxa-Michael addition
  作者：G. Srinivas Rao、Neela Sudhakar、B. Venkateswara Rao、S. Jeelani Basha

  DOI：10.1016/j.tetasy.2010.07.018

  日期：2010.8

  The formal synthesis of 3-epi jaspine B was achieved by using a stereoselective intramolecular oxa-Michael addition. The diacetate derivative of 3-epi jaspine B was also synthesized. (C) 2010 Elsevier Ltd. All rights reserved.