methyl 3-tert-butoxycarbonylamino-5-hydroxybenzoate | 141311-38-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 3-tert-butoxycarbonylamino-5-hydroxybenzoate
• 英文别名: 3-tert-butoxycarbonylamino-5-hydroxy-benzoic acid methyl ester；Methyl 3-((tert-butoxycarbonyl)amino)-5-hydroxybenzoate；methyl 3-hydroxy-5-[(2-methylpropan-2-yl)oxycarbonylamino]benzoate
• CAS: 141311-38-8
• 化学式: C₁₃H₁₇NO₅
• 分子量: 267.282
• InChiKey: BTCBPJXBHNJYAM-UHFFFAOYSA-N

物化性质

• 熔点：
  146 °C(Solv: chloroform (67-66-3))
• 沸点：
  378.1±32.0 °C(Predicted)
• 密度：
  1.244±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3-tert-butoxycarbonylamino-5-hydroxybenzoate 在 盐酸 、 水 、 potassium carbonate 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 8.0h， 生成 3-[3-[2-[2-[2-[2-[2-[[4-(2-Azatricyclo[10.4.0.04,9]hexadeca-1(16),4,6,8,12,14-hexaen-10-yn-2-yl)-4-oxobutanoyl]amino]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]propanoylamino]-5-prop-2-ynoxybenzoic acid
  参考文献：
  名称：

  [EN] SKELETAL MUSCLE DELIVERY PLATFORMS AND METHODS OF USE
  [FR] PLATEFORMES D'ADMINISTRATION À DES MUSCLES SQUELETTIQUES ET MÉTHODES D'UTILISATION

  摘要：

  本公开涉及将有效载荷有针对性地且高效地引导至体内骨骼肌细胞的传递平台。所述传递平台包括靶向配体（例如具有亲和力的化合物，包括α-v-β-6整合素）和药代动力学/药效学（PK/PD）调节剂，以促进有效载荷传递到细胞，包括骨骼肌细胞。适用于本公开的传递平台的有效载荷包括RNAi剂，可以链接或结合到传递平台上，在体内传递时，可以抑制骨骼肌细胞的基因表达。还描述了包括骨骼肌细胞传递平台的药物组合物，以及用于治疗各种疾病和疾病的方法，其中传递治疗有效载荷至骨骼肌细胞是可取的。

  公开号：

  WO2022056269A1
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 3-氨基-5-羟基苯甲酸甲酯 在 碳酸氢钠 作用下， 以 四氢呋喃 为溶剂， 反应 36.0h， 以83%的产率得到methyl 3-tert-butoxycarbonylamino-5-hydroxybenzoate
  参考文献：
  名称：

  Synthesis of the N-Acetylcysteamine Thioester of seco-Proansamitocin

  摘要：

  The enantioselective total synthesis of the N-acetylcysteamine thioester of seco-proansamitocin, a key biosynthetic intermediate of the highly potent antitumor agent ansamitocin, is described, which twice utilizes the Nagao acetate aldol reaction, as well as an indium-mediated alkynylation of a benzyl bromide followed by carboalumination. The key step is a Heck reaction between two terminal alkenes for merging the two major fragments.

  DOI：

  10.1021/ol052588q

文献信息

• Aromatic Borylation/Amidation/Oxidation:  A Rapid Route to 5-Substituted 3-Amidophenols
  作者：Feng Shi、Milton R. Smith、Robert E. Maleczka

  DOI：10.1021/ol060207i

  日期：2006.3.1

  5-Substituted 3-amidophenols are prepared by subjecting 3-substituted halobenzenes to an Ir-catalyzed aromatic borylation, followed by a Pd-catalyzed amidation, and finally an oxidation of the boronic ester intermediate. The entire C-H activation borylation/amidation/oxidation sequence can be accomplished without isolation of any intermediate arenes. Usefully, amide partners can include lactams, carbamates, and ureas.
• [EN] SKELETAL MUSCLE DELIVERY PLATFORMS AND METHODS OF USE<br/>[FR] PLATEFORMES D'ADMINISTRATION À DES MUSCLES SQUELETTIQUES ET MÉTHODES D'UTILISATION
  申请人：ARROWHEAD PHARMACEUTICALS INC

  公开号：WO2022056269A1

  公开（公告）日：2022-03-17

  The present disclosure relates to delivery platforms that specifically and efficiently direct payloads to skeletal muscle cells in a subject, in vivo. The delivery platforms diclosed herein include targeting ligands (such as compounds that have affinity for integrins, including alpha- v-beta-6) and pharmacokinetic/pharmacodynamic (PK/PD) modulators, to facilitate the delivery of payloads to cells, including to skeletal muscle cells. Suitable payloads for use in the delivery platforms disclosed herein include RNAi agents, which can be linked or conjugated to the delivery platofrms, and when delivered in vivo, provide for the inhibition of gene expression in skeletal muscle cells. Pharmaceutical compositions that include the skeletal muscle cell delivery platform are also described, as well as methods of use for the treatment of various diseases and disorders where delivery of a therapeutic payload to a skeletal muscle cell is desirable.

  本公开涉及将有效载荷有针对性地且高效地引导至体内骨骼肌细胞的传递平台。所述传递平台包括靶向配体（例如具有亲和力的化合物，包括α-v-β-6整合素）和药代动力学/药效学（PK/PD）调节剂，以促进有效载荷传递到细胞，包括骨骼肌细胞。适用于本公开的传递平台的有效载荷包括RNAi剂，可以链接或结合到传递平台上，在体内传递时，可以抑制骨骼肌细胞的基因表达。还描述了包括骨骼肌细胞传递平台的药物组合物，以及用于治疗各种疾病和疾病的方法，其中传递治疗有效载荷至骨骼肌细胞是可取的。
• Synthesis of the <i>N</i>-Acetylcysteamine Thioester of <i>s</i><i>eco</i>-Proansamitocin
  作者：Thomas Frenzel、Marco Brünjes、Monika Quitschalle、Andreas Kirschning

  DOI：10.1021/ol052588q

  日期：2006.1.1

  The enantioselective total synthesis of the N-acetylcysteamine thioester of seco-proansamitocin, a key biosynthetic intermediate of the highly potent antitumor agent ansamitocin, is described, which twice utilizes the Nagao acetate aldol reaction, as well as an indium-mediated alkynylation of a benzyl bromide followed by carboalumination. The key step is a Heck reaction between two terminal alkenes for merging the two major fragments.