N-[(3aR,4R,6S,6aR)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-2-methylpropan-1-imine oxide | 1173283-38-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[(3aR,4R,6S,6aR)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-2-methylpropan-1-imine oxide
• CAS: 1173283-38-9
• 化学式: C₁₆H₂₇NO₆
• 分子量: 329.393
• InChiKey: OUZIJLHQOIFWLP-XVIXHAIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  74.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-[(3aR,4R,6S,6aR)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-2-methylpropan-1-imine oxide 、 (2,2-dichloro-1-methoxy-vinyloxy)-trimethysilane 在 zinc(II) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 6.5h， 以382.7 mg的产率得到(S)-4,4-dichloro-2-((3aR,4R,6S,6aR)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-3-isopropylisoxazolidin-5-one
  参考文献：
  名称：

  α,α-Dichloroisoxazolidinones for the Synthesis and Chemoselective Peptide Ligation of α-Peptide α-Ketoacids

  摘要：

  In seeking to develop an iterative approach to the preparation of alpha-oligopeptides by the chemoselective amide-forming coupling of alpha-ketoacids and hydroxylamines, we have designed and synthesized novel enantiopure monomers. Key to our approach is the use of alpha,alpha-dichloroacids as masked alpha-ketoacids. The preparation of these monomers, their coupling with alpha-ketoacids, and the conversion of the alpha,alpha-dichloroacids to alpha-ketoacids is described. These studies provide a first step to a conceptually unique approach to peptide synthesis that does not require activating reagents or produce chemical byproducts.

  DOI：

  10.3987/com-10-s(e)106
• 作为产物：
  描述：

  N-羟基-2,3:5,6-二-O-(1-甲基亚乙基)-alpha-D-式闭式式呋喃葡萄糖基胺结构 、 异丁醛 在 magnesium sulfate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 N-[(3aR,4R,6S,6aR)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-2-methylpropan-1-imine oxide
  参考文献：
  名称：

  α,α-Dichloroisoxazolidinones for the Synthesis and Chemoselective Peptide Ligation of α-Peptide α-Ketoacids

  摘要：

  In seeking to develop an iterative approach to the preparation of alpha-oligopeptides by the chemoselective amide-forming coupling of alpha-ketoacids and hydroxylamines, we have designed and synthesized novel enantiopure monomers. Key to our approach is the use of alpha,alpha-dichloroacids as masked alpha-ketoacids. The preparation of these monomers, their coupling with alpha-ketoacids, and the conversion of the alpha,alpha-dichloroacids to alpha-ketoacids is described. These studies provide a first step to a conceptually unique approach to peptide synthesis that does not require activating reagents or produce chemical byproducts.

  DOI：

  10.3987/com-10-s(e)106

文献信息

• CONJUGATES OF CELL BINDING MOLECULES WITH CYTOTOXIC AGENTS
  申请人：ZHAO R. Yongxin

  公开号：US20170157262A1

  公开（公告）日：2017-06-08

  A conjugate of a potent cytotoxic agent with a cell-surface receptor binding molecule having a formula (I), wherein T, L, m, n, Y, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 12 , and R 13 are defined herein, can be used for targeted treatment of cancer, autoimmune disease, and infectious disease.

  一种具有公式（I）的细胞表面受体结合分子的强效细胞毒药物的共轭物，其中T、L、m、n、Y、R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R12和R13在此定义，可用于靶向治疗癌症、自身免疫疾病和传染病。
• Conjugates of Cell Binding Molecules with Cytotoxic Agents
  申请人：Zhao R. Yongxin

  公开号：US20170296663A1

  公开（公告）日：2017-10-19

  A conjugate of a potent cytotoxic agent with a cell-surface receptor binding molecule having a Formula (I), wherein T, L, m, n, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , and R 13 are defined herein, can be used for targeted treatment of cancer, autoimmune disease, and infectious disease.

  一种有效的细胞毒性药物的共轭物，带有具有化学式（I）的细胞表面受体结合分子，其中T、L、m、n、R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12和R13在此有定义，可用于靶向治疗癌症、自身免疫疾病和传染性疾病。
• Stereoselective synthesis of tubuvaline methyl ester and tubuphenylalanine, components of tubulysins, tubulin polymerization inhibitors
  作者：Taku Shibue、Toshihiro Hirai、Iwao Okamoto、Nobuyoshi Morita、Hyuma Masu、Isao Azumaya、Osamu Tamura

  DOI：10.1016/j.tetlet.2009.04.046

  日期：2009.7

  stereoselective synthesis of tubuvaline methyl ester (2) was accomplished by 1,3-dipolar cycloaddition of nitrone d-6 and acrylic acid derivatives 7 as a key step. The synthesis of tubuphenylalanine (3) was conducted by an aldol reaction of a boron enolate of (S)-4-isopropyl-3-propionyl-2-oxazolidinone (13) with aldehyde 14, readily prepared from phenylalanine, followed by Barton deoxygenation under radical

  描述了微管蛋白溶素的两种成分，微管蛋白聚合抑制剂的合成研究。作为关键步骤，通过硝酮d- 6和丙烯酸衍生物7的1，3-偶极环加成反应完成了tubuvaline甲酯（2）的高度立体选择性合成。tubuphenylalanine的（合成3）通过（的硼烯醇化物的醛醇缩合反应进行小号）-4-异丙基-3-丙酰基-2-恶唑烷酮（13）与醛14，容易从苯丙氨酸制备，下后跟Barton脱氧根本条件。
• Conjugates of cell binding molecules with cytotoxic agents
  申请人：Hangzhou DAC Biotech Co., Ltd.

  公开号：US10399941B2

  公开（公告）日：2019-09-03

  A conjugate of a potent cytotoxic agent with a cell-surface receptor binding molecule having a Formula (I), wherein T, L, m, n, R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, and R13 are defined herein, can be used for targeted treatment of cancer, autoimmune disease, and infectious disease.

  强效细胞毒剂与细胞表面受体结合分子的共轭物具有式（I），其中 T、L、m、n、R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12 和 R13 在本文中定义，可用于癌症、自身免疫性疾病和传染性疾病的靶向治疗。
• [EN] CONJUGATES OF CELL BINDING MOLECULES WITH CYTOTOXIC AGENTS<br/>[FR] CONJUGUÉS DE MOLÉCULE DE LIAISON CELLULAIRE ET D'AGENTS CYTOTOXIQUES
  申请人：HANGZHOU DAC BIOTECH CO LTD

  公开号：WO2014009774A1

  公开（公告）日：2014-01-16

  A conjugate of a potent cytotoxic agent with a cell-surface receptor binding molecule having a formula (I), wherein T, L, m, n, Y, R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R12, and R13 are defined herein, can be used for targeted treatment of cancer, autoimmune disease, and infectious disease.