(2R,3R)-1,4-二(甲磺酰基氧基)丁烷-2,3-二醇 | 1947-62-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 中文名称: (2R,3R)-1,4-二(甲磺酰基氧基)丁烷-2,3-二醇
• 中文别名: (2R,3R)-1,4-二(甲磺酰氧代)丁烷-2,3-二醇
• 英文名称: treosulfan
• 英文别名: D-threitol 1,4-bis(methanesulfonate)；threitol 1,4-bis(methanesulfonate)；D-Threitol-1,4-bis-methansulfonat；D-Threitol-1,4-bis(methanesulfonate)；[(2R,3R)-2,3-dihydroxy-4-methylsulfonyloxybutyl] methanesulfonate
• CAS: 1947-62-2
• 化学式: C₆H₁₄O₈S₂
• 分子量: 278.304
• InChiKey: YCPOZVAOBBQLRI-PHDIDXHHSA-N

物化性质

• 熔点：
  102-103 °C
• 沸点：
  607.0±55.0 °C(Predicted)
• 密度：
  1.562±0.06 g/cm3(Predicted)
• 分解：
  When heated to decomposition it emits toxic fumes of /sulfur oxides/.

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  144
• 氢给体数：
  2
• 氢受体数：
  8

安全信息

• 海关编码：
  2905499000

反应信息

• 作为反应物：
  描述：

  (2R,3R)-1,4-二(甲磺酰基氧基)丁烷-2,3-二醇 在 potassium hydroxide 作用下， 以 乙醚 、 水 为溶剂， 以60%的产率得到(2R)-2-[(2R)-环氧乙烷-2-基]环氧乙烷
  参考文献：
  名称：

  2,2'-生物环氧乙烷的手性。

  摘要：

  合成了2,2'-生物环氧乙烷的两种对映异构体，并通过旋光法，振动圆二色性（VCD）和拉曼光学活性（ROA）在各种溶剂中彻底研究了它们的手性。在B3LYP / AUG-CC-pVTZ水平密度泛函理论（DFT）计算显示三个构象（存在ģ +，g ^ - ，和顺式分别为51，44和5％吉布斯种群的分离的分子，） 。两个主要的构象异构体的人口比例进行了修改为显示更高介电常数（溶剂ģ -形式降低，而G ^ +形式增加）。通过使用可极化连续体模型（PCM），通过与时间有关的DFT计算可以正确地再现特定溶剂在不同旋光度值下的行为，但对于苯，必须使用显式溶剂模型。最后，VCD和ROA光谱完全由DFT / PCM计算为玻尔兹曼平均再现ģ +和G ^ -构象。

  DOI：

  10.1002/chir.22814
• 作为产物：
  描述：

  [(4R,5R)-2,2-二甲基-1,3-二氧戊环-4,5-二基]二(亚甲基)二甲烷磺酸酯 在 甲烷磺酸 作用下， 以 乙醇 、 水 为溶剂， 以81%的产率得到(2R,3R)-1,4-二(甲磺酰基氧基)丁烷-2,3-二醇
  参考文献：
  名称：

  2,2'-生物环氧乙烷的手性。

  摘要：

  合成了2,2'-生物环氧乙烷的两种对映异构体，并通过旋光法，振动圆二色性（VCD）和拉曼光学活性（ROA）在各种溶剂中彻底研究了它们的手性。在B3LYP / AUG-CC-pVTZ水平密度泛函理论（DFT）计算显示三个构象（存在ģ +，g ^ - ，和顺式分别为51，44和5％吉布斯种群的分离的分子，） 。两个主要的构象异构体的人口比例进行了修改为显示更高介电常数（溶剂ģ -形式降低，而G ^ +形式增加）。通过使用可极化连续体模型（PCM），通过与时间有关的DFT计算可以正确地再现特定溶剂在不同旋光度值下的行为，但对于苯，必须使用显式溶剂模型。最后，VCD和ROA光谱完全由DFT / PCM计算为玻尔兹曼平均再现ģ +和G ^ -构象。

  DOI：

  10.1002/chir.22814

文献信息

• Platinum(II) complex and processes for preparing the same
  申请人：Sunkyong Industries, Ltd.

  公开号：US05395947A1

  公开（公告）日：1995-03-07

  Disclosed herein are novel platinum(II) complexes having a potent anti-tumor activity which are represented by the formula (1), ##STR1## wherein R.sub.1 and R.sub.2, which may be the same or different, are a hydrogen atom or a C.sub.1-4 alkyl group, respectively, or jointly form a cycloalkane group together with the carbon atom attached thereto; two Xs jointly form a group represented by formula (a) or (b) wherein, R.sub.3 is a hydrogen atom or a methyl group; R.sub.4 and R.sub.5, which may be the same or different, are a hydrogen atom or a C.sub.1-4 alkyl group, respectively, or jointly form a cyclobutane together with the carbon thereto; and the absolute configurations at the respective chiral centers in the 4,5-bis(aminomethyl)-1,3-dioxolane moiety are (4R,5R) or (4S,5S); processes for the preparing the same; and their use for treating animal or human cancer. Further, disclosed herein are novel intermediates useful for the preparation of the platinum(II) complexes and processes for preparing said intermediates.

  本文披露了具有强效抗肿瘤活性的新型铂（II）配合物，其化学式为（1），其中R.sub.1和R.sub.2，可以相同也可以不同，分别为氢原子或C.sub.1-4烷基基团，或者与连接的碳原子共同形成环烷基基团；两个X共同形成由化学式（a）或（b）表示的基团，其中，R.sub.3为氢原子或甲基基团；R.sub.4和R.sub.5，可以相同也可以不同，分别为氢原子或C.sub.1-4烷基基团，或者与碳原子共同形成环丁烷基团；以及4,5-双(氨甲基)-1,3-二氧杂环戊烷基团中各立体中心的绝对构型为（4R,5R）或（4S,5S）；制备这些配合物的方法；以及它们用于治疗动物或人类癌症的用途。此外，本文还披露了用于制备铂（II）配合物的新型中间体以及制备这些中间体的方法。
• Synthesis and Antitumor Activity of a Series of [2-Substituted-4,5-bis(aminomethyl)-1,3-Dioxolane]platinum(II) Complexes
  作者：Dae-Kee Kim、Ganghyeok Kim、Jongsik Gam、Yong-Baik Cho、Hun-Taek Kim、Joo-Ho Tai、Key H. Kim、Weon-Seon Hong、Jae-Gahb Park

  DOI：10.1021/jm00036a013

  日期：1994.5

  The synthesis, physical properties, antitumor activity, structure-activity relationships, and nephrotoxicity of a series of [2-substituted-4,5-bis(aminomethyl)-1,3-dioxolane]platinum(II) complexes are described. The 42 platinum(II) complexes having a seven-membered ring structure in this series have been prepared and characterized by 1H NMR, 13C NMR, IR, FAB-MS, and elemental analysis. All members

  描述了一系列[2-取代-4,5-双（氨基甲基）-1,3-二氧戊环]铂（II）配合物的合成，物理性质，抗肿瘤活性，结构活性关系和肾毒性。已制备了该系列中具有七元环结构的42种铂（II）配合物，并通过1 H NMR，13 C NMR，IR，FAB-MS和元素分析对其进行了表征。该系列的所有成员均设计成在其载体配体中具有1,3-二氧戊环环部分以增加水溶性。铂配合物的溶解度与在4,5-双（氨基甲基）-1,3-二氧戊环载体配体中剩余配体和2-取代基的性质有关。通常，在4，5-双（氨基甲基）-1，3-二氧戊环部分中具有两个不同的R 1和R 2取代基的化合物比具有相同取代基的化合物具有更高的水溶性。该系列的大多数成员对移植到小鼠中的小鼠L1210白血病细胞显示出优异的抗肿瘤活性，并且优于顺铂和卡铂。（4R，5R）-立体异构体1a-h在（1,1-环丁烷二羧基）铂（II）配合物中比相应的（4S，5S）-立体
• Stereoisomere 1,4-Di-O-methansulfonyl-butan-1,2,3,4-tetrole
  作者：P.W. Feit

  DOI：10.1016/s0040-4039(01)91680-6

  日期：1961.1
• Interstrand and Intrastrand DNA−DNA Cross-Linking by 1,2,3,4-Diepoxybutane:  Role of Stereochemistry
  作者：Soobong Park、Christopher Anderson、Rachel Loeber、Mahadevan Seetharaman、Roger Jones、Natalia Tretyakova

  DOI：10.1021/ja051979x

  日期：2005.10.1

  1,2,3,4-Diepoxybutane (DEB) is a bifunctional electrophile capable of forming DNA-DNA and DNA-protein cross-links. DNA alkylation by DEB produces N7-(2'-hydroxy-3',4'-epoxybut-1'-yl)-guanine monoadducts, which can then form 1,4-bis-(guan-7-yl)-2,3-butanediol (bis-N7G-BD) lesions. All three optical isomers of DEB are produced metabolically from 1,3-butadiene, but S,S-DEB is the most cytotoxic and genotoxic. In the present work, interstrand and intrastrand DNA-DNA cross-linking by individual DEB stereoisomers was investigated by PAGE, mass spectrometry, and stable isotope labeling. S,S-, R,R-, and meso-diepoxides were synthesized from L-dimethyl-2,3-O-isopropylidene-tartrate, D-dimethyl-2,3-O-isopropyl id e ne-tart rate, and meso-erythritol, respectively. Total numbers of bis-N7G-BD lesions (intrastrand and interstrand) in calf thymus DNA treated separately with S,S-, R,R-, or meso-DEB (0.01-0.5 mM) were similar as determined by capillary HPLC-ESI+-MS/MS of DNA hydrolysates. However, denaturing PAGE has revealed that S,S-DEB produced the highest number of interchain cross-links in 5'-GGC-3/3'-CCG-5' sequences. Intrastrand adduct formation by DEB was investigated by a novel methodology based on stable isotope labeling HPLC-ESI+-MS/MS. Meso DEB treatment of DNA duplexes containing 5'-[1,7,NH2-N-15(3),2-C-13-G]GC-3'/3'-CCG-5' and 5'-GGC-3/3'-CC[N-15(3),2-C-13-G]-5' trinucleotides gave rise to comparable numbers of 12-intrastrand and 1,3-interstrand bis-N7G-BD cross-links, while S,S DEB produced few intrastrand lesions. R,P-DEB treated DNA contained mostly 1,3-interstrand bis-N7G-BD, along with smaller amounts of 1,2-interstrand and 1,2-intrastrand adducts. The effects of DEB stereochemistry on its ability to form DNA-DNA cross-links may be rationalized by the spatial relationships between the epoxy alcohol side chains in stereoisomeric N7-(2'-hydroxy-3',4'-epoxybut-1'-yl)-guanine adclucts and their DNA environment. Different cross-linking specificities of DEB stereoisomers provide a likely structural basis for their distinct biological activities.
• Zr-promoted cyclization of diynes bearing C2-chirality: synthesis and properties of new chiral conjugated molecules
  作者：Ken-Tsung Wong、Ruei-Tang Chen

  DOI：10.1016/s0040-4039(02)00520-8

  日期：2002.4

  Conjugated oligomers bearing 4,5,6,7-tetrahydro-5S,6S-dioctyloxybenzothiophene as a central linkage were synthesized by Negishi's reagent (n-Bu2ZrCp2) promoted intramolecular cyclization of a diyne and subsequent Suzuki coupling reactions. The chirality in the central linkage originated from tartaric acid, which induced the conjugated backbone of oligomers to exhibit interesting optical activity. (C) Elsevier Science Ltd. All rights reserved.