(1'S,4R)-4-(3',3'-bisethylthio-1'-p-methoxybenzyloxypropyl)-2,2-dimethyl-1,3-dioxolane | 152453-71-9

• 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: (1'S,4R)-4-(3',3'-bisethylthio-1'-p-methoxybenzyloxypropyl)-2,2-dimethyl-1,3-dioxolane
• 英文别名: 4-[3,3-bis-ethylsulfanyl-1-(4-methoxy-benzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolane；(4R)-4-[(1S)-3,3-bis(ethylsulfanyl)-1-[(4-methoxyphenyl)methoxy]propyl]-2,2-dimethyl-1,3-dioxolane
• CAS: 152453-71-9
• 化学式: C₂₀H₃₂O₄S₂
• 分子量: 400.604
• InChiKey: HCYZABKCQIDRFA-ZWKOTPCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  87.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1'S,4R)-4-(3',3'-bisethylthio-1'-p-methoxybenzyloxypropyl)-2,2-dimethyl-1,3-dioxolane 在 mercury dichloride 、 mercury(II) oxide 作用下， 以 水 、 乙腈 为溶剂， 以85%的产率得到2-deoxy-3-O-<(4-methoxyphenyl)methyl>-4,5-O-(1-methylethylidene)-D-erythro-pentose
  参考文献：
  名称：

  First total synthesis of mueggelone

  摘要：

  All the four possible stereoisomers of mueggelone, an inhibitor of fish development, were efficiently synthesized in a stereoselective manner starting from D-arabinose, and the absolute configuration was determined to be 9R,12S,13S. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01285-5
• 作为产物：
  描述：

  1-(2,2-dimethyl-[1,3]dioxolan-4-yl)-3,3-bis-ethylsulfanyl-propan-1-ol 、 4-甲氧基氯苄 在 sodium hydride 、 二甲基亚砜 作用下， 反应 4.0h， 以100%的产率得到(1'S,4R)-4-(3',3'-bisethylthio-1'-p-methoxybenzyloxypropyl)-2,2-dimethyl-1,3-dioxolane
  参考文献：
  名称：

  由碳水化合物前体合成两种新的美登木素生物碱类化合物

  摘要：

  摘要美登素（1）是一种具有显着抗癌活性的大环天然产物。通过使用烯丙基硫醚阴离子在C-6处烷基化，将D-葡萄糖的衍生物（4）转化为美登木素生物碱环下周边的模型化合物（10），然后氧化为亚砜和[2,3] -亚磺酸酯的-σ重排。另外，公开了一种方法，用于将美登木素生物碱类的上周边的一部分从D-阿拉伯糖转化为Chiron（18）。

  DOI：

  10.1080/07328309808002895

文献信息

• Synthesis of Two New Maytansinoid Model Compounds from Carbohydrate Precursors
  作者：Thomas E. Goodwin、Kimberley R. Cousins、Heidi M. Crane、Phyllis O. Eason、Timothy E. Freyaldenhoven、Charles C. Harmon、Brock K. King、Christine D. LaRocca、Robert L. Lile、Shari G. Orlicek、Ronald W. Pelton、Omer L. Shedd、John S. Swanson、Joseph W. Thompson

  DOI：10.1080/07328309808002895

  日期：1998.4

  product with significant anti-cancer activity. A derivative (4) of D-glucal is converted to a model compound (10) for the lower periphery of the maytansinoid ring via alkylation at C-6 using an allylic sulfide anion, followed by oxidation to the sulfoxide and [2,3]-sigmatropic rearrangement to the sulfenate ester. In addition, a method is disclosed for conversion of D-arabinose to a chiron (18) for a portion

  摘要美登素（1）是一种具有显着抗癌活性的大环天然产物。通过使用烯丙基硫醚阴离子在C-6处烷基化，将D-葡萄糖的衍生物（4）转化为美登木素生物碱环下周边的模型化合物（10），然后氧化为亚砜和[2,3] -亚磺酸酯的-σ重排。另外，公开了一种方法，用于将美登木素生物碱类的上周边的一部分从D-阿拉伯糖转化为Chiron（18）。
• Laulimalide Analogs and Uses Thereof
  申请人：Gallagher Jr M. Brian

  公开号：US20070287745A1

  公开（公告）日：2007-12-13

  The present invention provides compounds having formula I: and pharmaceutically acceptable derivatives thereof, wherein R 1 -R 10 , q, t, X 0 , X 1 , A, B, D, E, G, J, K, L, M and Z are as described generally and in classes and subclasses herein, and additionally provides pharmaceutical compositions thereof, and methods for the use thereof for the treatment of disorders associated with cellular hyperproliferation.

  本发明提供具有公式I的化合物及其药学上可接受的衍生物，其中R1-R10、q、t、X0、X1、A、B、D、E、G、J、K、L、M和Z如本文中一般和在类别和子类别中所述，并且此外还提供其药物组合物以及使用它们治疗与细胞过度增殖相关的疾病的方法。
• Total Synthesis of the Macrolide Antitumor Antibiotic Lankacidin C
  作者：Andrew S. Kende、Kun Liu、Istvan Kaldor、Gilbert Dorey、Kevin Koch

  DOI：10.1021/ja00136a025

  日期：1995.8

  The first total synthesis of natural (-)-lankacidin C (I) has been achieved by a convergent, enantioselective sequence starting from D-arabinose and L-aspartic acid, proceeding through the tricyclic carbamate 15 as an advanced relay intermediate. Specifically, the beta-lactam diene intermediate 41 is acylated by the thiopyridyl ester 34c. The resulting beta-ketolactam 42 is stereospecifically reduced by KEt(3)BH to carbinol 43, which on desilylation undergoes acid-catalyzed N --> O acyl migration to yield the delta-lactone 44. The derived iodo aldehyde 46 undergoes Stille coupling to give tetraene 54a, which upon Stork-Takahashi cyclization to ketone 56 and CBS reduction gives the key relay 15. N-acylation of the latter, and then regioselective carbamate scission followed by Dess-Martin oxidation, produces the target antibiotic (-)-lankacidin C (1).
• First total synthesis of mueggelone
  作者：Ken Ishigami、Hajime Motoyoshi、Takeshi Kitahara

  DOI：10.1016/s0040-4039(00)01285-5

  日期：2000.11

  All the four possible stereoisomers of mueggelone, an inhibitor of fish development, were efficiently synthesized in a stereoselective manner starting from D-arabinose, and the absolute configuration was determined to be 9R,12S,13S. (C) 2000 Elsevier Science Ltd. All rights reserved.
• [EN] LAULIMALIDE ANALOGS WITH ANTI-CANCER ACTIVITITY<br/>[FR] ANALOGUES DE LAULIMALIDE ET UTILISATIONS DE CEUX-CI
  申请人：EISAI CO LTD

  公开号：WO2005030779A3

  公开（公告）日：2008-01-24