prop-2-enyl (3S,4R)-3-hydroxy-5-methyl-4-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate | 878630-46-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: prop-2-enyl (3S,4R)-3-hydroxy-5-methyl-4-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate
• CAS: 878630-46-7
• 化学式: C₁₅H₂₇NO₅
• 分子量: 301.383
• InChiKey: IHOGZENDMHTZOL-WCQYABFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  prop-2-enyl (3S,4R)-3-hydroxy-5-methyl-4-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate 在 四(三苯基膦)钯 吗啉 、 盐酸 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 二乙胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 生成 (3S,4R)-3-hydroxy-4-[[(2S)-2-[[(2R)-2-[[(E,3S)-3-hydroxy-7-tritylsulfanylhept-4-enoyl]amino]propanoyl]amino]-3-tritylsulfanylpropanoyl]amino]-5-methylhexanoic acid
  参考文献：
  名称：

  A total synthesis of spiruchostatin A

  摘要：

  We achieved the total synthesis of the histone deacetylase inhibitor spiruchostatin A, as the prelude to the preparation of a combinatorial library of its analogues. Two key reactions were an asymmetric acetate aldol reaction using a Zr-enolate and macrolactonization Using the Shiina method. (c) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2005.12.031
• 作为产物：
  描述：

  Boc-D-缬氨酸 在 potassium carbonate 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 为溶剂， 生成 prop-2-enyl (3S,4R)-3-hydroxy-5-methyl-4-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate
  参考文献：
  名称：

  A total synthesis of spiruchostatin A

  摘要：

  We achieved the total synthesis of the histone deacetylase inhibitor spiruchostatin A, as the prelude to the preparation of a combinatorial library of its analogues. Two key reactions were an asymmetric acetate aldol reaction using a Zr-enolate and macrolactonization Using the Shiina method. (c) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2005.12.031

文献信息

• Depsipeptides and Their Therapeutic Use
  申请人：Ganesan Arasu

  公开号：US20100056435A1

  公开（公告）日：2010-03-04

  A compound of the general Structure (VII) or (VIII) including isoteres and pharmaceutically acceptable salts thereof, wherein R 1 , R 2 (where X=—CONR 6 —), R 3 and R 7 are the same or different and each represents an amino-acid side chain moiety; R 2 (where X=—CHZ—), R 4 and R 6 are the same or different and each represents hydrogen, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, or C 2 -C 6 alkynyl; K represents a linear or branched chain of carbon atoms and containing 1-10 atoms; L represents a moiety capable of chelating zinc in the active site of a histone deacetylase (HDAC) or of conversion to such a moiety in vivo (by hydrolysis or reduction, for example); M is a linear or branched chain of carbon or other atoms and containing 1-10 atoms, and capable of undergoing in vivo cleavage to give Structure (VII); and Z is a heteroatom bonded to the macrocycle by a single or double bond, and any other group bonded to Z is H or a protecting group.

  化合物的一般结构（VII）或（VIII）的化合物，包括同位素体和药学上可接受的盐，其中R1、R2（其中X = -CONR6-）、R3和R7相同或不同，每个代表一种氨基酸侧链基团；R2（其中X = -CHZ-）、R4和R6相同或不同，每个代表氢、C1-C6烷基、C2-C6烯基或C2-C6炔基；K代表一条含有1-10个碳原子的线性或支链；L代表一种能够在组蛋白去乙酰化酶（HDAC）的活性位点中螯合锌或在体内转化为这种基团的基团（例如通过水解或还原）；M是一条含有1-10个碳或其他原子的线性或支链，能够在体内发生裂解以得到结构（VII）；Z是通过单个或双键与大环结合的杂原子，与Z结合的任何其他基团是H或保护基团。
• Total synthesis of cyclodepsipeptide spiruchostatin A on silyl-linked polymer-support
  作者：Masahito Yoshida、Ken-ichi Sasahara、Takayuki Doi

  DOI：10.1016/j.tet.2015.07.064

  日期：2015.10

  Solid-phase total synthesis of cyclodepsipeptide spiruchostatin A (1) has been achieved. Initially, immobilization of the Boc-d-Val-statine derivative 3 via the hindered β-hydroxy group was efficiently achieved using polymer-supported silyl triflate. Subsequently, the peptide chain was successfully extended on the polymer-support to yield the tetrapeptide cyclization precursor 2 with high purity.

  固相合成环二肽spiruchostatin A（1）。最初，通过受阻的β-羟基有效地实现了Boc - d -Val-他汀衍生物3的固定化，这是通过使用聚合物负载的三氟甲磺酸甲硅烷基酯来实现的。随后，肽链成功地在聚合物载体上延伸，以产生具有高纯度的四肽环化前体2。2-甲基-6-硝基苯甲酸酐（MNBA）介导的2的大内酯化在聚合物载体上顺利进行，以提供大内酯12。最后，从聚合物载体上释放大内酯，然后原位形成二硫键，从而提供了螺旋藻抑素A（1），总收益率为17％。
• US8865655B2
  申请人：——

  公开号：US8865655B2

  公开（公告）日：2014-10-21
• A total synthesis of spiruchostatin A
  作者：Takayuki Doi、Yusuke Iijima、Kazuo Shin-ya、A. Ganesan、Takashi Takahashi

  DOI：10.1016/j.tetlet.2005.12.031

  日期：2006.2

  We achieved the total synthesis of the histone deacetylase inhibitor spiruchostatin A, as the prelude to the preparation of a combinatorial library of its analogues. Two key reactions were an asymmetric acetate aldol reaction using a Zr-enolate and macrolactonization Using the Shiina method. (c) 2005 Published by Elsevier Ltd.