ethyl (R)-2-[(4'R)-2',2'-dimethyl-1,3-dioxolan-4'-yl]-2-hydroxyacetate | 114184-94-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl (R)-2-[(4'R)-2',2'-dimethyl-1,3-dioxolan-4'-yl]-2-hydroxyacetate
• 英文别名: ethyl ((2R,3R)-3,4-O-isopropylidene-2,3,4-trihydroxybutanoate)；ethyl (2R,3R)-3,4-O-isopropylidene-2,3,4-trihydroxybutanoate；ethyl 1,2-O-methyl-ethylidene D-erythronate；ethyl 3,4-O-methylethylidene D-erythronate；ethyl 3,4-O-ethylidene D-threonate；ethyl (2R)-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxyacetate
• CAS: 114184-94-0
• 化学式: C₉H₁₆O₅
• 分子量: 204.223
• InChiKey: HTZGTIDNENEORY-RNFRBKRXSA-N

物化性质

• 沸点：
  72 °C(Press: 0.0075 Torr)
• 密度：
  1.142±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (R)-2-[(4'R)-2',2'-dimethyl-1,3-dioxolan-4'-yl]-2-hydroxyacetate 在 吡啶 、 三氟甲磺酸酐 、 sodium nitrite 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以74%的产率得到ethyl (2S)-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxyacetate
  参考文献：
  名称：

  Synthesis of Imidazolo-Piperidinopentoses as Nagstatine Analogues

  摘要：

  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.

  DOI：

  10.1002/1099-0690(200111)2001:21<4111::aid-ejoc4111>3.0.co;2-7
• 作为产物：
  描述：

  碘乙烷 、 D-异抗坏血酸 在 三乙胺 作用下， 以 丙酮 为溶剂， 生成 ethyl (R)-2-[(4'R)-2',2'-dimethyl-1,3-dioxolan-4'-yl]-2-hydroxyacetate
  参考文献：
  名称：

  2,3-二脱氧-2-氟-2,3-内-亚甲基-戊二酸和2,3-二脱氧-2-氟-3- C-羟甲基-2,3-内-亚甲基-戊呋喃糖酶的合成及其应用构型锁定双环核苷的制备

  摘要：

  由d-甘油醛和2,3-二脱氧-2-氟-3- C-羟甲基-2,3-内-亚甲基构筑受保护的2,3-二脱氧-2-氟-2,3-内-亚甲基五呋喃糖酶描述了通过相应的氟代烯丙醇上的Simmons-Smith型立体选择性环丙烷化反应衍生自d-异抗坏血酸的五呋喃糖酶。相应的构象锁定的糖修饰的尿苷和鸟苷核苷的合成是通过Vorbrüggen或Mitsunobu方法实现的。在2D NOESY NMR实验的基础上，对新型核苷进行立体化学确认。2'，3'-二脱氧-2'-氟-3'- C-羟甲基-2'，3'-内含物的分析通过X射线晶体学分析得到-亚甲基-尿苷的主要构象参数，并表明呋喃环采用o E / o T 1，East pucker。在基于丙型肝炎病毒（HCV）细胞的复制子测定中发现尿苷和鸟苷核苷是无活性的，这一点在针对HCV NS5B聚合酶检查相应的三磷酸核苷时得到了证实。

  DOI：

  10.1021/jo502712g

文献信息

• Allylic Stereocontrol of the Intramolecular Diels-Alder Reaction
  作者：Michael J. Lilly、Natalie A. Miller、Alison J. Edwards、Anthony C. Willis、Peter Turner、Michael N. Paddon-Row、Michael S. Sherburn

  DOI：10.1002/chem.200401215

  日期：2005.4.8

  The stereochemical outcome of the intramolecular Diels-Alder reaction of ester-linked 1,3,8-nonatrienes can be controlled by substituents about a stereogenic center attached to C1. The scope and limitations of this approach have been investigated, with variation in substrate structure about the allylic stereocenter and the dienophile. The stereochemical outcomes of these reactions are explained by

  酯连接的1,3,8-壬烯的分子内Diels-Alder反应的立体化学结果可通过围绕C1的立体中心的取代基控制。已经研究了这种方法的范围和局限性，其中关于烯丙基立体中心和亲双烯体的底物结构有所变化。这些反应的立体化学结果通过参考B3 LYP / 6-31G（d）过渡结构进行解释。报道了对烯丙醇衍生物的构象偏好的新见解，其结果使得可以解释反应中π-非对面选择性和顺/反（即内/外）选择性的不同水平。
• Total synthesis and the anticancer activity of (+)-spisulosine
  作者：Milica Fabišíková、Miroslava Martinková、Simona Hirková、Jozef Gonda、Martina Bago Pilátová、Gabriela Gönciová

  DOI：10.1016/j.carres.2016.09.010

  日期：2016.11

  The total synthesis of the anticancer agent (+)-spisulosine has been accomplished. The strategy involved a substrate-controlled aza-Claisen rearrangement to establish the erythro-configured amino-alcohol motif followed by deoxygenation to create a methyl side-chain. Subsequent Wittig olefination then permitted the construction of the carbon backbone of the target molecule. To investigate the antiproliferative

  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）。
• 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。
• Stem Cell Culture Methods
  申请人：Adams David Roger

  公开号：US20120202287A1

  公开（公告）日：2012-08-09

  The invention provides methods for reversibly inhibiting stem cell differentiation wherein a compound of formula (I) is contacted with a stem cell. The invention further provides a method for preparing a culture medium, a culture medium supplement and a composition comprising a compound of formula (I).

  该发明提供了一种可逆抑制干细胞分化的方法，其中将式(I)的化合物与干细胞接触。该发明还提供了一种制备培养基、培养基添加剂和包含式(I)化合物的组合物的方法。
• 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。