methyl (Z)-6-[(1S,2R)-1-amino-2-[(2R)-1-[tert-butyl(diphenyl)silyl]oxypropan-2-yl]cyclopentyl]hex-2-enoate | 1026515-31-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: methyl (Z)-6-[(1S,2R)-1-amino-2-[(2R)-1-[tert-butyl(diphenyl)silyl]oxypropan-2-yl]cyclopentyl]hex-2-enoate
• CAS: 1026515-31-0
• 化学式: C₃₁H₄₅NO₃Si
• 分子量: 507.789
• InChiKey: AXSBYWUOGZIDLA-ZDFXEFIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (Z)-6-[(1S,2R)-1-amino-2-[(2R)-1-[tert-butyl(diphenyl)silyl]oxypropan-2-yl]cyclopentyl]hex-2-enoate 在 水 、 potassium carbonate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 tert-butyl (2'R,6S,9aR)-2'-[(2R)-1-[tert-butyl(diphenyl)silyl]oxypropan-2-yl]-2-oxospiro[3,4,7,8,9,9a-hexahydro-1H-quinolizine-6,1'-cyclopentane]-3-carboxylate
  参考文献：
  名称：

  Studies towards the total synthesis of halichlorine: asymmetric synthesis of the spiroquinolizidine subunit

  摘要：

  The C1-C15 spiroquinolizidine subunit (cf. 2) of the marine natural product halichlorine (1) was prepared in 12 steps starting from the known 'Meyers-lactam' 5. The synthesis involves a B-alkyl-Suzuki coupling followed by a highly stereoselective intramolecular Michael addition and an intramolecular Mannich ring closure. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01170-3
• 作为产物：
  描述：

  (R)-2-((1R,2S)-2-Allyl-2-tert-butoxycarbonylamino-cyclopentyl)-propionic acid 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 9-borabicyclo[3.3.1]nonane dimer 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 methyl (Z)-6-[(1S,2R)-1-amino-2-[(2R)-1-[tert-butyl(diphenyl)silyl]oxypropan-2-yl]cyclopentyl]hex-2-enoate
  参考文献：
  名称：

  Total Synthesis of (+)-Halichlorine: An Inhibitor of VCAM-1 Expression

  摘要：

  The diastereoselective addition of the highly functionalized organozinc compound 1 to the aldehyde 2 in the presence of the chiral amino alcohol 3 (-->4) is a key step in the first total synthesis of (+)-halichlorine. A series of protections/deprotections and a macrolaconization complete the synthesis. Halichlorine selectively inhibits the expression of the cell adhesion molecule VCAM-1. TBS=tert-butyldimethylsilyl.

  DOI：

  10.1002/(sici)1521-3773(19991203)38:23<3542::aid-anie3542>3.0.co;2-i

文献信息

• Studies towards the total synthesis of halichlorine: asymmetric synthesis of the spiroquinolizidine subunit
  作者：Dirk Trauner、Samuel J Danishefsky

  DOI：10.1016/s0040-4039(99)01170-3

  日期：1999.9

  The C1-C15 spiroquinolizidine subunit (cf. 2) of the marine natural product halichlorine (1) was prepared in 12 steps starting from the known 'Meyers-lactam' 5. The synthesis involves a B-alkyl-Suzuki coupling followed by a highly stereoselective intramolecular Michael addition and an intramolecular Mannich ring closure. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Total Synthesis of (+)-Halichlorine: An Inhibitor of VCAM-1 Expression
  作者：Dirk Trauner、Jacob B. Schwarz、Samuel J. Danishefsky

  DOI：10.1002/(sici)1521-3773(19991203)38:23<3542::aid-anie3542>3.0.co;2-i

  日期：——

  The diastereoselective addition of the highly functionalized organozinc compound 1 to the aldehyde 2 in the presence of the chiral amino alcohol 3 (-->4) is a key step in the first total synthesis of (+)-halichlorine. A series of protections/deprotections and a macrolaconization complete the synthesis. Halichlorine selectively inhibits the expression of the cell adhesion molecule VCAM-1. TBS=tert-butyldimethylsilyl.