methyl 2,4-dideoxy-4-(ethylamino)-3-O-methyl-α-L-threo-pentopyranoside | 129834-76-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: methyl 2,4-dideoxy-4-(ethylamino)-3-O-methyl-α-L-threo-pentopyranoside
• 英文别名: (3S,4S,6R)-N-ethyl-4,6-dimethoxyoxan-3-amine
• CAS: 129834-76-0
• 化学式: C₉H₁₉NO₃
• 分子量: 189.255
• InChiKey: WHILQIMYAXDVDK-XHNCKOQMSA-N

物化性质

• 沸点：
  253.7±40.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  39.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  氯甲酸-9-芴基甲酯 、 methyl 2,4-dideoxy-4-(ethylamino)-3-O-methyl-α-L-threo-pentopyranoside 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以95%的产率得到methyl 2,4-dideoxy-4-amino>-3-O-methyl-α-L-threo-pentopyranoside
  参考文献：
  名称：

  Studies Related to the Carbohydrate Sectors of Esperamicin and Calicheamicin: Definition of the Stability Limits of the Esperamicin Domain and Fashioning of a Glycosyl Donor from the Calicheamicin Domain

  摘要：

  The core trisaccharide regions of esperamicin and the aryltetrasaccharide region of calicheamicin have been synthesized. The minimum protection modalities necessary to stabilize structures against rearrangement to an isomeric azafuranose series were ascertained (see compounds 12 and 65). Deprotection of the 2-(trimethylsilyl)ethoxycarbonyl carbamate from 65 led to azafuranose 14 characterized as methyl glycoside 15. Using this insight, it was possible to fashion, for the first time, a pre-glycosyl donor (see compound 128) corresponding to the complete arylsaccharide sector of calicheamicin gamma(1)(I) at the oxidation level of the domain. Among the key assembly strategies were the conversion of alpha-thiophenylpseudoglycals to allal derivatives (see 44 --> 45); the interfacing of epoxide-mediated glycosylation with iodoglycosylation (see 30 --> 47 --> 48); the synthesis of hydroxylamine glycosides via triflate displacement (see 61 + 91 --> 101); and a new route to p-hydroxybenzonitriles (see formation of 86).

  DOI：

  10.1021/ja00126a013
• 作为产物：
  描述：

  1-[(1R,4R,6R)-4-甲氧基-3-氧杂-7-氮杂双环[4.1.0]庚-7-基]乙酮 在 lithium aluminium tetrahydride 、 硫酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.33h， 生成 methyl 2,4-dideoxy-4-(ethylamino)-3-O-methyl-α-L-threo-pentopyranoside
  参考文献：
  名称：

  加利车霉素的氨基糖成分（E环）的一个有效的立体选择性合成γ 1我

  摘要：

  一种简单，高效，立体选择性的甲基2,4-二脱氧-4-（乙基氨基）-3 - O-甲基-β-L-苏-戊吡喃糖苷2的合成，对应于E的单糖单元（E环）描述了加利车霉素1。合成程序利用甲基2-脱氧-β-D-核糖吡喃糖苷3作为对映体纯原料，并通过中间体活化的氮丙啶12的酸甲醇分解，分6步得到所需的氨基糖2，令人满意的高总收率（60％ ）。在合成过程的任何时候都不需要分离阶段。

  DOI：

  10.1016/0957-4166(96)00074-2

文献信息

• [EN] CALICHEAMICIN DERIVATIVES AND ANTIBODY DRUG CONJUGATES THEREOF<br/>[FR] DÉRIVÉS DE CALICHÉAMICINE ET CONJUGUÉS ANTICORPS-MÉDICAMENTS DE CEUX-CI
  申请人：PFIZER

  公开号：WO2018138591A1

  公开（公告）日：2018-08-02

  The present invention is directed to novel calicheamicin derivatives useful as payloads in antibody-drug-conjugates (ADC's), and to payload-linker compounds and ADC compounds comprising the same; to pharmaceutical compositions comprising the same and to methods for using the same to treat pathological conditions such as cancer.

  本发明涉及新型calicheamicin衍生物，用作抗体-药物偶联物（ADC）的有效载荷，以及包含相同有效载荷-连接剂化合物和ADC化合物；涉及包含它们的药物组合物以及使用它们治疗诸如癌症等病理状态的方法。
• Improved stereoselective synthesis of both methyl α- and β-glycosides corresponding to the amino sugar component of the E Ring of calicheamicin γ1I and esperamicin A1
  作者：Fabrizio Badalassi、Paolo Crotti、Lucilla Favero、Franco Macchia、Mauro Pineschi

  DOI：10.1016/s0040-4020(97)00921-6

  日期：1997.10

  monosaccharide component (α and β-anomer) of the E Ring of calicheamicin γ1I and esperamicin A1 has been synthetized by an efficient and improved stereoselective procedure starting from methyl 2-deoxy-α- and β-D-ribopyranoside. The synthetic procedure makes use, in each case, of a cyclic sulphate and of the regioselective ring opening of an intermediate activated aziridine.

  的E环的单糖组分（α和β端基异构体）刺孢霉素γ 1我和埃斯波霉素阿1已经通过从甲基2-脱氧- α-和β-d-ribopyranoside开始的有效和改进的立体选择性方法合成。在每种情况下，合成方法都使用环状硫酸盐和中间体活化的氮丙啶的区域选择性开环。
• An efficient stereoconvergent synthesis of the 4-ethylamino-2,4-dideoxy-l-threo-pentopyranose component of the calicheamicins and esperamicins
  作者：Eugene A. Mash、Sandeep K. Nimkar

  DOI：10.1016/0040-4039(93)85082-8

  日期：1993.1

  A stereconvergent synthesis of the 4-ethylamino-2,4-dideoxy-L-threo-pentopyranose coonponent of calicheamicins γ1, γ1I, α2I, and esperamicin A1b from methyl 2-deoxy-β-D-ribopyranoside is described. The synthesis requires eight steps in each branch. The overall yield is 54%. This synthesis should be adaptable for syntheses of the corresponding 4-methylamino)-2,4-dideoxy- L-threo- and 4-isopropylamino-2

  的stereconvergent合成4-乙基氨基-2,4-二脱氧L-苏-pentopyranose coonponent刺孢霉素γ的1，γ 1我，α 2予，和埃斯波甲1b中由2-脱氧- β-d-ribopyranoside是描述。该综合在每个分支中需要八个步骤。总产率为54％。该合成应适合于合成其他加利车霉素和艾司帕米霉素抗生素的相应的4-甲基氨基）-2,4-二脱氧-L-苏-和4-异丙基氨基-2.4-双脱氧-L-苏-戊糖成分。
• Synthesis of the CD and E ring systems of the calicheamicin γ₁^Ioligosaccharide
  作者：K. C. Nicolaou、R. D. Groneberg、N. A. Stylianides、T. Miyazaki

  DOI：10.1039/c39900001275

  日期：——

  Syntheses of the CD and E ring systems of calicheamicin γ1I as compounds (2) and (3)(for CD) and (4) and (5)(for E) in their naturally occurring forms are reported.

  报告了卡利卡明 δ³1I 的 CD 和 E 环系统化合物 (2) 和 (3)（针对 CD）以及 (4) 和 (5)（针对 E）的天然存在形式的合成。
• Groneberg; Miyazaki; Stylianides, Journal of the American Chemical Society, 1993, vol. 115, # 17, p. 7593 - 7611
  作者：Groneberg、Miyazaki、Stylianides、Schulze、Stahl、Schreiner、Suzuki、Iwabuchi、Smith、Nicolaou

  DOI：——

  日期：——