(3R,4S)-4-[(tert-butyloxycarbonyl)-amino]-6-methyl-1-hepten-3-ol | 107599-95-1

• 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: (3R,4S)-4-[(tert-butyloxycarbonyl)-amino]-6-methyl-1-hepten-3-ol
• 英文别名: tert-butyl N-[(3R,4S)-3-hydroxy-6-methylhept-1-en-4-yl]carbamate
• CAS: 107599-95-1
• 化学式: C₁₃H₂₅NO₃
• 分子量: 243.346
• InChiKey: HFORXYBQJVPDTQ-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,4S)-4-[(tert-butyloxycarbonyl)-amino]-6-methyl-1-hepten-3-ol 以100%的产率得到
  参考文献：
  名称：

  THAISRIVONGS, SUVIT

  摘要：

  DOI：
• 作为产物：
  描述：

  N-叔丁氧羰基-L-亮氨醇 在 sodium hypochlorite 、 2,2,6,6-四甲基哌啶氧化物 、 碳酸氢钠 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.75h， 生成 (3R,4S)-4-[(tert-butyloxycarbonyl)-amino]-6-methyl-1-hepten-3-ol
  参考文献：
  名称：

  An Efficient Synthesis of the Taxane-Derived Anticancer Agent ABT-271

  摘要：

  ABT-271, 1, has been identified as a promising anticancer agent. ABT-271 is a novel taxane possessing a CS-(R)-hydroxyl group as opposed to a CS-ketone which is present in Taxol and Taxotere. To further evaluate ABT-271 as a potential anticancer agent, an efficient synthesis was developed which allows the large scale synthesis of ABT-271. Ketalization of the 7,9-diol of 9-DHAB-III, 2, allows selective removal of th:e CI-acetate with phenyllithium. The resulting C13-hydroxyl group is then acylated using LiHMDS and beta -lactam 22 to give ABT-271 in protected form. The protecting groups were removed first by acidic hydrolysis followed by basic hydrolysis to provide ABT-271. Application of this synthetic sequence provided over 600 g of ABT-271, 1.

  DOI：

  10.1021/jo0057203

文献信息

• An efficient synthetic method for Z-fluoroalkene dipeptide isosteres: Application to the synthesis of the dipeptide isostere of Sta-Ala
  作者：Yuko Nakamura、Midori Okada、Minoru Koura、Manabu Tojo、Akio Saito、Azusa Sato、Takeo Taguchi

  DOI：10.1016/j.jfluchem.2005.11.016

  日期：2006.5

  followed by reaction with alkyl halides provided the corresponding (Z)-α-alkylated products in high yields. The latter reaction was applied to the preparation of the dipeptide (Z)-fluoroalkene isostere of Sta-Ala, which is the central dipeptide unit in Pepstatin, a natural inhibitor of aspartate proteases.

  发现具有δ-羟基的γ，γ-二氟-α，β-烯酸酯与三烷基铝（R 3 Al）的反应被CuI·2LiCl促进，并以SN2'方式进行，从而产生了α-烷基化的（Z）-γ-氟-β，γ-烯酸酯，同时用Me 2 CuLi还原γ，γ-二氟-α，β-烯酸酯，然后与卤代烷反应，得到相应的（Z）-α-烷基化产物高产。后一反应用于制备Sta-Ala的二肽（Z）-氟烯烃等排物，它是天冬氨酸蛋白酶的天然抑制剂Pepstatin中的中心二肽单元。
• Stereoselective vinylation of amino aldehydes using 2-trimethylsilylethylidentriphenylphosphorane
  作者：Maurizio Franciotti、André Mann、Maurizio Taddei

  DOI：10.1016/s0040-4039(00)93602-5

  日期：1991.11

  2-Trimethylsilylethylidentriphenylphosphorane reacts stereoselectively with α-amino aldehydes giving the Cram chelation controlled product of vinylation of the carbonyl group. The olefinic 1,2-amino alcohols obtained with this reaction are important intermediates for the preparation of peptides analogues and they were employed for the preparation of N-Boc-statine.

  2-三甲基甲硅烷基乙基三苯苯基膦烷与α-氨基醛立体选择性地反应，得到羰基乙烯基化的Cram螯合控制产物。通过该反应获得的烯属1,2-氨基醇是制备肽类似物的重要中间体，并且被用于制备N-Boc-他汀。
• Lipase-catalyzed Transesterification of Methyl 2-Substituted 3-Hydroxy-4-pentenoates and its Synthetic Application to the Taxol Side Chain
  作者：Tadakatsu Mandai、Tetsuta Oshitari、Masafumi Susowake

  DOI：10.1055/s-2002-34247

  日期：——

  Syn-and anti-methyl 2-substituted 3-hydroxy-4-pentenoates were efficiently resolved in lipase-catalyzed transesterification. This protocol was successfully applied to the synthesis of the taxol side chain.

  辛基和反式甲基2取代的3-羟基-4-戊烯酸酯在脂酶催化的转酯化反应中高效分离。该方法成功应用于紫杉醇侧链的合成。
• Process for the preparation of a dipeptide isostere
  申请人：Abbott Laboratories

  公开号：US05130468A1

  公开（公告）日：1992-07-14

  A process and intermediates useful for the preparation of (E)-alkene dipeptide isosteres are disclosed.

  本发明揭示了一种用于制备(E)-烯烃二肽同分异构体的过程和中间体。
• A Modular Synthetic Approach toward Exhaustively Stereodiversified Ligand Libraries
  作者：Tiffany Malinky Gierasch、Milan Chytil、Mary T. Didiuk、Julie Y. Park、Jeffrey J. Urban、Steven P. Nolan、Gregory L. Verdine

  DOI：10.1021/ol006560k

  日期：2000.12.1

  This report describes a modular approach to the synthesis of stereodiversified natural product like libraries. Monomers 2 and 3 were coupled in parallel by silyl tethered olefin metathesis to generate all 16 stereoisomers of cis-enediols 1. All 16 stereoisomers were incorporated into chimerae having flanking peptidic segments. These chimerae exhibited a broad range of hydrophobicities, raising the possibility that stereochemical variation might be used to tune the pharmacologic properties of small molecules.