(4S)-3-((3S,2R)-3-hydroxy-2,4-dimethylpent-4-enoyl)-4-benzyl-1,3-oxazolidin-2-one | 400007-14-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4S)-3-((3S,2R)-3-hydroxy-2,4-dimethylpent-4-enoyl)-4-benzyl-1,3-oxazolidin-2-one
• 英文别名: (4S)-3-[(2R,3S)-3-hydroxy-2,4-dimethylpent-4-enoyl]-4-benzyl-1,3-oxazolidin-2-one；(4S)-4-benzyl-3-[(2R,3S)-3-hydroxy-2,4-dimethylpent-4-enoyl]oxazolidin-2-one；(4S, 3S, 2R)-4-BENZYL-3-(3-HYDROXY-2,4-dimethylpent-4-enoyl) oxazolidin-2-one；(4S)-4-benzyl-3-[(2R,3S)-3-hydroxy-2,4-dimethylpent-4-enoyl]-1,3-oxazolidin-2-one
• CAS: 400007-14-9
• 化学式: C₁₇H₂₁NO₄
• 分子量: 303.358
• InChiKey: NZNQVFXLNMUYFI-VHDGCEQUSA-N

物化性质

• 沸点：
  485.7±38.0 °C(Predicted)
• 密度：
  1.201±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S)-3-((3S,2R)-3-hydroxy-2,4-dimethylpent-4-enoyl)-4-benzyl-1,3-oxazolidin-2-one 在 2,6-二甲基吡啶 、 甲醇 、 锂硼氢 、 草酰氯 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 生成
  参考文献：
  名称：

  迈向环吖啶胺 A 和 B 的全合成

  摘要：

  已经考虑了两种不同的策略来实现间吖啶胺 A 和 B 的全合成。基于霍纳-维蒂希烯化反应的第一种方法是不成功的。第二种方法涉及去对称化、高度非对映选择性醛醇缩合、Wittig 烯化、酰胺形成和最终束缚形成，提供了一种先进的中间体39，其中所有立体中心都存在于间吖啶胺 A 和 B 中。

  DOI：

  10.1016/j.tetlet.2022.153640
• 作为产物：
  描述：

  (S)-4-苄基-3-丙酰基-2-噁唑烷酮 在 sodium hexafluoroantimonate 、 三乙胺 、 三氟乙酸 、 magnesium chloride 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 24.5h， 生成 (4S)-3-((3S,2R)-3-hydroxy-2,4-dimethylpent-4-enoyl)-4-benzyl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  非对映选择性卤化镁催化的手性N-酰基恶唑烷酮的反羟醛反应

  摘要：

  报道了一种基于手性助剂的直接醛醇反应。该反应在镁盐中具有催化作用，并通过与三甲基氯硅烷的硅烷化作用促进。分离出的加合物具有高非对映选择性（高达 32:1 dr）并且有利于抗醛醇非对映异构体 B。反应操作简单，可以在环境气氛下进行，无需严格排除水。许多加合物是高度结晶的，无需色谱法即可分离单个非对映异构体。

  DOI：

  10.1021/ja0119548

文献信息

• [EN] ANALOGS OF DISCODERMOLIDE AND DICTYOSTATIN-1, INTERMEDIATES THEREFOR AND METHODS OF SYNTHESIS THEREOF<br/>[FR] ANALOGUES DE DISCODERMOLIDE ET DE DICTYOSTATINE-1, INTERMEDIAIRES CORRESPONDANTS, ET PROCEDES DE SYNTHESE CORRESPONDANTS
  申请人：UNIV PITTSBURGH

  公开号：WO2004022552A1

  公开（公告）日：2004-03-18

  A compound of the following structure: wherein R1 is H, an alkyl group, an aryl group, an alkenyl group, an alkynyl group, or a halogen atom; R2 is H, an alkyl group, an aryl group, a benzyl group, a trityl group, -SiRaRbRc, CH2ORd, or CORe; Ra, Rb and Rc are independently an alkyl group or an aryl group; Rd is an alkyl group, an aryl group, an alkoxylalkyl group, -RiSiRaRbRc or a benzyl group, wherein Ri is an alkylene group; Re is an alkyl group, an allyl group, a benzyl group, an aryl group, an alkoxy group, or -NRgRh, wherein Rg and Rh are independently H, an alkyl group or an aryl group; R3 is (CH2)n where n is and integer in the range of 0 to 5, -CH2CH(CH3)-, -CH=CH-, -CH=C(CH3)-, or -C=-C-; R4 is (CH2)p where p is an integer in the range of 4 to 12, -(CHRkl)yl (CHRk2)y2(CHRk3)y3(CHRk4)y4(CHRk5)y5C(Rsl )=C(Rs2)C(Rs3)=C(Rs4)-, -(CHRk1 )yl (CHRk2)y2(CHRk3)y3(CHRk4)y4(CHRk5)y5CH(Rs I)CH(Rs2)C(Rs3)=C(Rs4)-, -(CHRk1)yl (CHRk2)y2(CHRk3)y3(CHRk4)y4(CHRks)y5C(Rsl)=C(Rs2)CH(Rs3)CH(Rs4)-, -(CHRkI )yl (CHRk2)y2(CHRk3)y3(CHRk4)y4(CHRk5)y5CH(Rsl)CH(Rs2)CH(Rs3)CH(R s4)-, wherein y1 and y2 are 1 and y3, y4 and y5 are independently 0 or 1, Rk1, Rk2, Rk3, Rk4 and Rk5 are independently H, CH3, or OR2a, and Rs1, Rs2, Rs3, and Rs4 are independently H or CH3, wherein R2a is H, an alkyl group, an aryl group, a benzyl group, a trityl group, -SiRaRbRc, CH2ORd, or CORe; and R5 is H or OR2b, wherein R2b is H, an alkyl group, an aryl group, an aryl group, a benzyl group, a trityl group, -SiRaRbRc, CH2ORd, or CORe; provided that the compound is not dictyostatin 1.

  以下是该结构的化合物：其中R1为H、烷基基团、芳基、烯基基团、炔基基团或卤素原子；R2为H、烷基基团、芳基、苄基、三苄基、-SiRaRbRc、 ORd或CORe；Ra、Rb和Rc独立地为烷基基团或芳基；Rd为烷基基团、芳基、烷氧基烷基团、-RiSiRaRbRc或苄基，其中Ri为烷基烷基团；Re为烷基基团、烯丙基基团、苄基、芳基、烷氧基或-NRgRh，其中Rg和Rh独立地为H、烷基基团或芳基；R3为(CH2)n，其中n为0到5范围内的整数，- CH(CH3)-、-CH=CH-、-CH=C( )-或-C=-C-；R4为( )p，其中p为4到12范围内的整数，-(CHRkl)yl (CHRk2)y2(CHRk3)y3(CHRk4)y4(CHRk5)y5C(Rsl )=C(Rs2)C(Rs3)=C(Rs4)-、-(CHRk1 )yl (CHRk2)y2(CHRk3)y3(CHRk4)y4(CHRk5)y5CH(Rs I)CH(Rs2)C(Rs3)=C(Rs4)-、-(CHRk1)yl (CHRk2)y2(CHRk3)y3(CHRk4)y4(CHRks)y5C(Rsl)=C(Rs2)CH(Rs3)CH(Rs4)-、-(CHRkI )yl (CHRk2)y2(CHRk3)y3(CHRk4)y4(CHRk5)y5CH(Rsl)CH(Rs2)CH(Rs3)CH(R s4)-，其中y1和y2为1，y3、y4和y5独立地为0或1，Rk1、Rk2、Rk3、Rk4和Rk5独立地为H、 或OR2a，Rs1、Rs2、Rs3和Rs4独立地为H或 ，其中R2a为H、烷基基团、芳基、苄基、三苄基、-SiRaRbRc、 ORd或CORe；R5为H或OR2b，其中R2b为H、烷基基团、芳基、芳基、苄基、三苄基、-SiRaRbRc、 ORd或CORe；前提是该化合物不是dictyostatin 1。
• Synthesis and biological evaluation of (−)-dictyostatin and stereoisomers
  作者：Youseung Shin、Jean-Hugues Fournier、Arndt Brückner、Charitha Madiraju、Raghavan Balachandran、Brianne S. Raccor、Michael C. Edler、Ernest Hamel、Rachel P. Sikorski、Andreas Vogt、Billy W. Day、Dennis P. Curran

  DOI：10.1016/j.tet.2007.05.033

  日期：2007.8

  Total syntheses of (-)-dictyostatin, 6,16-bis-epi-dictyostatin, 6,14,19-tris-epi-dictyostatin and a number of other isomers and analogs are reported. Three main fragments-top, middle and bottom-were first assembled and then joined by olefination or anionic addition reactions. After appending the two dienes at either end of the molecule, macrolactonization and deprotection completed the syntheses. The

  报告了 (-)-dictyostatin、6,16-bis-epi-dictyostatin、6,14,19-tris-epi-dictyostatin 和许多其他异构体和类似物的总合成。三个主要片段——顶部、中间和底部——首先组装，然后通过烯化或阴离子加成反应连接。在分子的任一端附加两个二烯后，大环内酯化和脱保护完成合成。这项工作证明了 (-)-dictyostatin 的相对和绝对构型。这些化合物通过基于细胞的微管质量增加和抗增殖活性的测量、体外微管蛋白聚合试验以及与紫杉醇在微管上的结合位点的竞争试验进行评估。
• Synthetic Studies on the Nhatrangins: Stereoselective Access to an Advanced Aldehyde Intermediate
  作者：Ludovic Raffier、Olivier Piva

  DOI：10.1002/ejoc.201201338

  日期：2013.2

  strategies have been considered to achieve the first total synthesis of nhatrangins A and B. The first approach based on a cross metathesis (CM) reaction was unsuccessful. The second, which combined a highly stereoselective alkylation, a diastereoselective aldolization, and finally an esterification, furnished an advanced aldehyde intermediate bearing the three contiguous stereogenic centres and the expected

  已经考虑了两种不同的策略来实现首次全合成 nhatrangins A 和 B。基于交叉复分解 (CM) 反应的第一种方法是不成功的。第二个结合了高度立体选择性烷基化、非对映选择性醛醇化和最后的酯化，提供了带有三个连续立体中心和预期侧链的高级醛中间体。
• Analogs of discodermolide and dictyostatin-1, intermediates therefor and methods of synthesis thereof
  申请人：——

  公开号：US20040186165A1

  公开（公告）日：2004-09-23

  A compound of the following structure: 1 wherein R 1 is H, an alkyl group, an aryl group, an alkenyl group, an alkynyl group, or a halogen atom; R 2 is H, an alkyl group, an aryl group, a benzyl group, a trityl group, —SiR a R b R c , CH 2 OR d , or COR e ; R a , R b and R c are independently an alkyl group or an aryl group; R d is an alkyl group, an aryl group, an alkoxylalkyl group, —R i SiR a R b R c or a benzyl group, wherein R i is an alkylene group; R e is an alkyl group, an allyl group, a benzyl group, an aryl group, an alkoxy group, or —NR g R h , wherein R g and R h are independently H, an alkyl group or an aryl group; R 3 is (CH 2 ) n where n is and integer in the range of 0 to 5, —CH 2 CH(CH 3 )—, —CH═CH—, —CH═C(CH 3 )—, or —C≡C—; R 4 is (CH 2 ) p where p is an integer in the range of 4 to 12, —(CHR k1 ) y1 (CHR k2 ) y2 (CHR k3 ) y3 (CHR k4 ) y4 (CHR k5 ) y5 C(R s1 )═C(R s2 )C(R s3 )═C(R s4 )—, —(CHR k1 ) y1 (CHR k2 ) y2 (CHR k3 ) y3 (CHR k4 ) y4 (CHR k5 ) y5 CH(R s1 )CH(R s2 )C(R s3 )═C(R s4 )—, —(CHR k1 ) y1 (CHR k2 ) y2 (CHR k3 ) y3 (CHR k4 ) y4 (CHR k5 ) y5 C(R s1 )═C(R s2 )CH(R s3 )CH(R s4 )—, —(CHR k1 ) y1 (CHR k2 ) y2 (CHR k3 ) y3 (CHR k4 ) y4 (CHR k5 ) y5 CH(R s1 )CH(R s2 )CH(R s3 )CH(R s4 )—, wherein y1 and y2 are 1 and y3, y4 and y5 are independently 0 or 1, R k1 , R k2 , R k3 , R k4 and R k5 are independently H, CH 3 , or OR 2a , and R s1 , R s2 , R s3 , and R s4 are independently H or CH 3 , wherein R 2a is H, an alkyl group, an aryl group, a benzyl group, a trityl group, —SiR a R b R c , CH 2 OR d , or COR e ; and R 5 is H or OR 2b , wherein R 2b is H, an alkyl group, an aryl group, an aryl group, a benzyl group, a trityl group, —SiR a R b R c , CH 2 OR d , or COR e ; provided that the compound is not dictyostatin 1.

  以下结构的化合物：其中R1为H、烷基、芳基、烯基、炔基或卤素原子；R2为H、烷基、芳基、苄基、三苯甲基、—SiRaRbRc、 ORd或CORe；Ra、Rb和Rc独立地为烷基或芳基；Rd为烷基、芳基、烷氧基烷基、—RiSiRaRbRc或苄基，其中Ri为烷基；Re为烷基、烯丙基、苄基、芳基、烷氧基或—NRgRh，其中Rg和Rh独立地为H、烷基或芳基；R3为(CH2)n，其中n为0至5范围内的整数，— CH(CH3)—、—CH═CH—、—CH═C( )—或—C≡C—；R4为( )p，其中p为4至12范围内的整数，—(CHRk1)y1(CHRk2)y2(CHRk3)y3(CHRk4)y4(CHRk5)y5C(Rs1)═C(Rs2)C(Rs3)═C(Rs4)—、—(CHRk1)y1(CHRk2)y2(CHRk3)y3(CHRk4)y4(CHRk5)y5CH(Rs1)CH(Rs2)C(Rs3)═C(Rs4)—、—(CHRk1)y1(CHRk2)y2(CHRk3)y3(CHRk4)y4(CHRk5)y5C(Rs1)═C(Rs2)CH(Rs3)CH(Rs4)—、—(CHRk1)y1(CHRk2)y2(CHRk3)y3(CHRk4)y4(CHRk5)y5CH(Rs1)CH(Rs2)CH(Rs3)CH(Rs4)—，其中y1和y2为1，y3、y4和y5独立地为0或1，Rk1、Rk2、Rk3、Rk4和Rk5独立地为H、 或OR2a，而Rs1、Rs2、Rs3和Rs4独立地为H或 ，其中R2a为H、烷基、芳基、苄基、三苯甲基、—SiRaRbRc、 ORd或CORe；而R5为H或OR2b，其中R2b为H、烷基、芳基、苄基、三苯甲基、—SiRaRbRc、 ORd或CORe；但该化合物不是二叉鞘菌素1。
• ANALOGS OF DICODERMOLIDE AND DICTYOSTATIN-1, INTERMEDIATES THEREFOR AND METHODS OF SYNTHESIS THEREOF
  申请人：CURRAN DENNIS P.

  公开号：US20090036691A1

  公开（公告）日：2009-02-05

  A compound of the following structure: wherein R 1 is H, an alkyl group, an aryl group, an alkenyl group, an alkynyl group, or a halogen atom; R 2 is H, an alkyl group, an aryl group, a benzyl group, a trityl group, —SiR a R b R c , CH 2 OR d , or COR e ; R a , R b and R c are independently an alkyl group or an aryl group; R d is an alkyl group, an aryl group, an alkoxylalkyl group, —R i SiR a R b R c or a benzyl group, wherein R i is an alkylene group; R e is an alkyl group, an allyl group, a benzyl group, an aryl group, an alkoxy group, or —NR g R h , wherein R g and R h are independently H, an alkyl group or an aryl group; R 3 is (CH 2 ) n where n is and integer in the range of 0 to 5, —CH 2 CH(CH 3 )—, —CH═CH—, —CH═C(CH 3 )—, or —C≡C—; R 4 , wherein y1 and y2 are 1 and y3, y4 and y5 are independently 0 or 1, R k1 , R k2 , R k3 , R k4 and R k5 are independently H, CH 3 , or OR 2a , and R s1 , R s2 , R s3 , and R s4 are independently H or CH 3 , wherein R 2a is H, an alkyl group, an aryl group, a benzyl group, a trityl group, —SiR a R b R c , CH 2 OR d , or COR e ; and R 5 is H or OR 2b , wherein R 2b is H, an alkyl group, an aryl group, an aryl group, a benzyl group, a trityl group, —SiR a R b R c , CH 2 OR d , or COR e .

  以下为结构式的化合物： 其中R1为H、烷基、芳基、烯基、炔基或卤素原子； R2为H、烷基、芳基、苯甲基、三苯甲基、—SiRaRbRc、 ORd或CORe； Ra、Rb和Rc独立地为烷基或芳基； Rd为烷基、芳基、烷氧基烷基、—RiSiRaRbRc或苯甲基，其中Ri为烷基； Re为烷基、烯丙基、苯甲基、芳基、烷氧基或—NRgRh，其中Rg和Rh独立地为H、烷基或芳基； R3为(CH2)n，其中n为0至5的整数，— CH(CH3)—、—CH═CH—、—CH═C( )—或—C≡C—； R4为H或OR2b，其中y1和y2为1，y3、y4和y5独立地为0或1，Rk1、Rk2、Rk3、Rk4和Rk5独立地为H、 或OR2a，而Rs1、Rs2、Rs3和Rs4独立地为H或 ，其中R2a为H、烷基、芳基、苯甲基、三苯甲基、—SiRaRbRc、 ORd或CORe；而R2b为H、烷基、芳基、苯甲基、三苯甲基、—SiRaRbRc、 ORd或CORe。