1-amino-1,4-anhydro-N-tert-butoxycarbonyl-5-O-tertbutyldimethylsilyl-1-deoxy-2,3-O-isopropylidene-D-ribitol | 178456-81-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 1-amino-1,4-anhydro-N-tert-butoxycarbonyl-5-O-tertbutyldimethylsilyl-1-deoxy-2,3-O-isopropylidene-D-ribitol
• 英文别名: tert-butyl (3aR,4R,6aS)-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate
• CAS: 178456-81-0
• 化学式: C₁₉H₃₇NO₅Si
• 分子量: 387.592
• InChiKey: YFLIDPCROXTRDO-QLFBSQMISA-N

物化性质

• 沸点：
  425.0±40.0 °C(Predicted)
• 密度：
  1.009±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.15
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-amino-1,4-anhydro-N-tert-butoxycarbonyl-5-O-tertbutyldimethylsilyl-1-deoxy-2,3-O-isopropylidene-D-ribitol 在 四氢呋喃 、 盐酸 、 ruthenium(IV) oxide 、 sodium periodate 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 四氯化碳 、 丙酮 、 乙腈 为溶剂， 反应 4.75h， 生成 (2S,3R,4S)-3,4-二羟基吡咯烷-2-羧酸
  参考文献：
  名称：

  Total synthesis of both enantiomers of trans-2,3-cis-3,4-dihydroxyproline

  摘要：

  Both enantiomers of trans-2,3-cis-3,4-dihydroxyproline, 4 and 5, have been stereoselectively synthesized from 2,3-O-isopropylidene-D-glyceraldehyde 1, by taking advantage of a divergent and parallel synthetic strategy, utilizing N-(tert-butoxycarbonyl)-2-(tert-butyldimethylsiloxy)pyrrole (TBSOP) as the common four-carbon synthon. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00123-1
• 作为产物：
  描述：

  N-(tert-butoxycarbonyl)-2-[(tert-butyldimethylsilyl)oxy]pyrrole 在 咪唑 、 2,6-二甲基吡啶 、 三乙基硅烷 、 二环己烷并-18-冠醚-6 、 potassium permanganate 、 sodium periodate 、 三氟化硼乙醚 、 silica gel 、 三乙基硼氢化锂 、 对甲苯磺酸 、 柠檬酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 39.16h， 生成 1-amino-1,4-anhydro-N-tert-butoxycarbonyl-5-O-tertbutyldimethylsilyl-1-deoxy-2,3-O-isopropylidene-D-ribitol
  参考文献：
  名称：

  Total synthesis of both enantiomers of trans-2,3-cis-3,4-dihydroxyproline

  摘要：

  Both enantiomers of trans-2,3-cis-3,4-dihydroxyproline, 4 and 5, have been stereoselectively synthesized from 2,3-O-isopropylidene-D-glyceraldehyde 1, by taking advantage of a divergent and parallel synthetic strategy, utilizing N-(tert-butoxycarbonyl)-2-(tert-butyldimethylsiloxy)pyrrole (TBSOP) as the common four-carbon synthon. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00123-1

文献信息

• Inhibition of LuxS by S-ribosylhomocysteine analogues containing a [4-aza]ribose ring
  作者：Venkata L.A. Malladi、Adam J. Sobczak、Tiffany M. Meyer、Dehua Pei、Stanislaw F. Wnuk

  DOI：10.1016/j.bmc.2011.07.043

  日期：2011.9

  LuxS (S-ribosylhomocysteinase) catalyzes the cleavage of the thioether linkage of S-ribosylhomocysteine (SRH) to produce homocysteine and 4,5-dihydroxy-2,3-pentanedione (DPD), the precursor to a small signaling molecule that mediates interspecies bacterial communication called autoinducer 2 (AI-2). Inhibitors of LuxS should interfere with bacterial interspecies communication and potentially provide a novel class of antibacterial agents. In this work, SRH analogues containing substitution of a nitrogen atom for the endocyclic oxygen as well as various deoxyriboses were synthesized and evaluated for LuxS inhibition. Two of the [4-aza] SRH analogues showed modest competitive inhibition (K-I similar to 40 mu M), while most of the others were inactive. One compound that contains a hemiaminal moiety exhibited time-dependent inhibition, consistent with enzyme-catalyzed ring opening and conversion into a more potent species (K-I* = 3.5 mu M). The structure-activity relationship of the designed inhibitors highlights the importance of both the homocysteine and ribose moieties for high-affinity binding to LuxS active site. (C) 2011 Elsevier Ltd. All rights reserved.
• Total synthesis of both enantiomers of trans-2,3-cis-3,4-dihydroxyproline
  作者：Franca Zanardi、Lucia Battistini、Marika Nespi、Gloria Rassu、Pietro Spanu、Mara Cornia、Giovanni Casiraghi

  DOI：10.1016/0957-4166(96)00123-1

  日期：1996.4

  Both enantiomers of trans-2,3-cis-3,4-dihydroxyproline, 4 and 5, have been stereoselectively synthesized from 2,3-O-isopropylidene-D-glyceraldehyde 1, by taking advantage of a divergent and parallel synthetic strategy, utilizing N-(tert-butoxycarbonyl)-2-(tert-butyldimethylsiloxy)pyrrole (TBSOP) as the common four-carbon synthon. Copyright (C) 1996 Elsevier Science Ltd