tert-butyl N-[(1R)-3-[tert-butyl(diphenyl)silyl]oxy-1-formylpropyl]carbamate | 905716-08-7

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: tert-butyl N-[(1R)-3-[tert-butyl(diphenyl)silyl]oxy-1-formylpropyl]carbamate
• 英文别名: tert-butyl [(2R)-4-{[tert-butyl(diphenyl)silyl]oxy}-1-oxobutan-2-yl]carbamate；tert-butyl N-[(2R)-4-[tert-butyl(diphenyl)silyl]oxy-1-oxobutan-2-yl]carbamate
• CAS: 905716-08-7
• 化学式: C₂₅H₃₅NO₄Si
• 分子量: 441.643
• InChiKey: FUSZBSLRVUQSLG-HXUWFJFHSA-N

物化性质

• 沸点：
  518.0±50.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.05
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(1R)-3-[tert-butyl(diphenyl)silyl]oxy-1-formylpropyl]carbamate 在 正丁基锂 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (R)-2-Amino-1-benzothiazol-2-yl-4-(tert-butyl-diphenyl-silanyloxy)-butan-1-ol
  参考文献：
  名称：

  Engineering d-amino acid containing novel protease inhibitors using catalytic site architecture

  摘要：

  The mechanism of proteolysis by serine proteases is a reasonably well-understood process. Typically, a histidine residue acting as a general base deprotonates the catalytic serine residue and the hydrolytic water molecule. We disclose here, the use of an unnatural D-amino acid as a strategic residue in P1 position, designed de novo based on the architecture of the protease catalytic site to impede the catalytic histidine residue at the stage of acyl-enzyme intermediate. Several probe molecules containing D-homoserine or its derivatives at P1 position are evaluated. Compounds 1, 6, and 8-10 produced up to 57% loss of activity against chymotrypsin. More potent and specific inhibitors could be designed with structure optimization as this strategy is completely general and can be used to design inhibitors against any serine or cysteine protease. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.08.019
• 作为产物：
  描述：

  叔丁基二苯基氯硅烷 在 咪唑 、 lithium aluminium tetrahydride 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 tert-butyl N-[(1R)-3-[tert-butyl(diphenyl)silyl]oxy-1-formylpropyl]carbamate
  参考文献：
  名称：

  Engineering d-amino acid containing novel protease inhibitors using catalytic site architecture

  摘要：

  The mechanism of proteolysis by serine proteases is a reasonably well-understood process. Typically, a histidine residue acting as a general base deprotonates the catalytic serine residue and the hydrolytic water molecule. We disclose here, the use of an unnatural D-amino acid as a strategic residue in P1 position, designed de novo based on the architecture of the protease catalytic site to impede the catalytic histidine residue at the stage of acyl-enzyme intermediate. Several probe molecules containing D-homoserine or its derivatives at P1 position are evaluated. Compounds 1, 6, and 8-10 produced up to 57% loss of activity against chymotrypsin. More potent and specific inhibitors could be designed with structure optimization as this strategy is completely general and can be used to design inhibitors against any serine or cysteine protease. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.08.019

文献信息

• A stereoselective total synthesis of (−)-andrachcinidine via an olefin cross-metathesis protocol
  作者：Palakodety Radha Krishna、G. Dayaker

  DOI：10.1016/j.tetlet.2007.08.053

  日期：2007.10

  A stereoselective total synthesis of 1-(2S,6R)-6-[(2S)-2-hydroxypentyl]-hexahydro-2-pyridinylacetone, (−)-andrachcinidine is reported. The strategy utilizes olefin cross-metathesis and intramolecular SN2 cyclization as the key steps.

  将1-立体选择性全合成（2小号，6 - [R）-6 - [（2-小号）-2-羟基戊基] -六氢-2- pyridinylacetone，（ - ） -报道andrachcinidine。该策略利用烯烃交叉复分解和分子内S N 2环化作为关键步骤。
• [EN] COMPOUNDS AND METHODS FOR THE TREATMENT OF PARASITIC DISEASES<br/>[FR] COMPOSÉS ET PROCÉDÉS POUR LE TRAITEMENT DE MALADIES PARASITAIRES
  申请人：BROAD INST INC

  公开号：WO2018175385A1

  公开（公告）日：2018-09-27

  Provided herein are compounds useful for the treatment of various parasitic diseases. These compounds, as well as pharmaceutically acceptable salts thereof may be formulated in pharmaceutical compostions, veterinary compositions and may be used in methods of treatment and/or prophylaxis of diseases spread by parasites, including malaria and cryptosporidiosis.

  本文提供了用于治疗各种寄生虫病的化合物。这些化合物以及其药用盐可以制成药物组合物、兽医组合物，并可用于治疗和/或预防由寄生虫传播的疾病，包括疟疾和隐孢子虫病。
• EP4245763
  申请人：——

  公开号：——

  公开（公告）日：——