N-Alloc-valine methylester | 110761-03-0

• 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: N-Alloc-valine methylester
• 英文别名: Alloc-Val-OMe；N-(allyloxycarbonyl)-L-valine methyl ester；N-allyloxycarbonylvaline methyl ester；methyl (2S)-3-methyl-2-(prop-2-enoxycarbonylamino)butanoate
• CAS: 110761-03-0
• 化学式: C₁₀H₁₇NO₄
• 分子量: 215.249
• InChiKey: WTWPYAIZADGYPB-QMMMGPOBSA-N

物化性质

• 沸点：
  298.0±33.0 °C(Predicted)
• 密度：
  1.048±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  N-Alloc-valine methylester 在 palladium diacetate 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 EtOCO-ValOMe
  参考文献：
  名称：

  Syntheses and reactions of silyl carbamates. 1. Chemoselective transformation of amino protecting groups via tert-butyldimethylsilyl carbamates

  摘要：

  DOI：

  10.1021/jo00290a015
• 作为产物：
  描述：

  L-缬氨酸甲酯盐酸盐 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 N-Alloc-valine methylester
  参考文献：
  名称：

  基于结构的环酰胺氨基甲酸酯衍生的人脑memapsin 2（β-分泌酶）抑制剂的设计。

  摘要：

  基于结合到美皮素2上的铅抑制剂（1，带有八个残基的OM99-2）的X射线晶体结构，设计和合成了一系列新颖的大环酰胺-氨基甲酸酯。研究了环的大小和取代基的作用。含有14至16元环的环酰胺氨基甲酸酯显示出对人脑memapsin 2（β-分泌酶）的低纳摩尔抑制力。

  DOI：

  10.1016/j.bmcl.2004.10.084

文献信息

• Isocyanates, Part 4. Convenient Phosgene-Free Method for the Synthesis and Derivatization of Enantiopure α-Isocyanato Carboxylic Acid Esters
  作者：Hans-Joachim Knölker、Tobias Braxmeier

  DOI：10.1055/s-1997-928

  日期：1997.8

  A novel phosgene-free procedure for the synthesis of α-isocyanato carboxylic acid esters starting from α-amino acid esters has been achieved. The isocyanates are obtained enantiomerically pure (>99% ee) by a DMAP-catalyzed isocyanation with di-tert-butyl dicarbonate, which proceeds in 10 min at room temperature. In situ derivatization of the isocyanates by reaction with amines and alcohols affords the corresponding enantiopure ureas and carbamates.

  以δ-氨基酸酯为起点合成δ-异氰酸羧酸酯的不含光气的新方法已经实现。通过 DMAP 催化与二碳酸二叔丁酯的异氰酸酯化反应，可在室温下 10 分钟内获得对映体纯度大于 99% 的异氰酸酯。异氰酸酯通过与胺和醇反应进行原位衍生，可得到相应的对映体脲和氨基甲酸酯。
• On the use of silylated nucleophiles in the palladium catalysed deprotection of allylic carboxylates and carbamates.
  作者：A. Merzouk、F. Guibé、A. Loffet

  DOI：10.1016/s0040-4039(00)93973-x

  日期：1992.1

  Palladium catalysts and silylamines, used together with a silylating electrophile (trimethylsilyl acetate), allow the deprotection of allyl carbamates under very mild and selective conditions.

  钯催化剂和甲硅烷基胺与甲硅烷基化的亲电子试剂（三甲基甲硅烷基乙酸酯）一起使用，可在非常温和和选择性的条件下使烯丙基氨基甲酸酯脱保护基。
• Tertiary-butyldimethylsilyl carbamate derivative and process for
  申请人：Suntory Limited

  公开号：US04837349A1

  公开（公告）日：1989-06-06

  A t-butyldimethylsilyl carbamate derivative and a process for producing the same are disclosed. Tertiary-butyldimethylsilyl carbamate derivatives having the following general formula (1) are intermediates for the production of a variety of carbamate esters that can be extensively used as drugs acting on the central nervous system or circulatory organs, as agrichemicals (e.g. insecticides and herbicides), or as antimicrobial agents; a process capable of economical and efficient production of such intermediates is also disclosed: ##STR1## where R.sup.1 is an alkyl group having 1-3 carbon atoms or a hydrogen atom; R.sup.2 is ##STR2## (where R.sup.3 is a hydrogen atom, an alkyl, alkenyl or aralkyl group having 1-10 carbon atoms, each of which groups may be substituted by a hydroxyl group, a t-butyldimethylsilyloxy group, a methylthio group, a lower alkoxycarbonyl group, a lower alkoxy group, an indolyl group or an imidazolyl group; R.sup.4 is a lower alkoxycarbonyl group, an N-alkylamido group having 2-6 carbon atoms, an O-tetrahydropyranylthr eonine methyl ester amido residue, an O-t-butyldimethylsilylthreonine methyl ester amido residue, a threonine methyl ester amido residue or --(CH.sub.2).sub.n --COOR.sup.5 (where n is an integer of 1-3 and R.sup.5 is a lower alkyl group), provided that R.sup.3 combines with R.sup.4 to form a cyclopentyl group, a cyclohexyl group, a tetrahydrofuranyl group or a dioxanyl group, these rings being optionally substituted by a lower alkyl group, a lower alkenyl group, a lower alkoxycarbonyl group or a lower alkoxycarbonylmethyl group); and R.sup.1 and R.sup.2, when taken together, form a 4- or 5-membered carbon ring, which may be substituted by a lower alkoxycarbonyl group or a t-butyldimethylsilyloxycarbonyl group.

  本发明公开了一种t-叔丁基二甲基硅烷基氨基甲酸酯衍生物及其制备方法。具有以下通用式（1）的三叔丁基二甲基硅烷基氨基甲酸酯衍生物是制备多种可广泛用作中枢神经系统或循环器官药物、农药（例如杀虫剂和除草剂）或抗微生物剂的氨甲酯的中间体；本发明还公开了一种能够经济高效地生产这种中间体的方法： 其中，R1是具有1-3个碳原子的烷基或氢原子；R2是##STR2##（其中R3是氢原子、具有1-10个碳原子的烷基、烯基或芳基烷基，这些基团中的每一个都可以被羟基、t-叔丁基二甲基硅氧基、甲硫基、低级烷氧羰基基团、低级烷氧基、吲哚基或咪唑基取代；R4是低级烷氧羰基基团、具有2-6个碳原子的N-烷基酰胺基团、O-四氢吡喃基缩酰亮氨酸甲酯酰基、O-t-叔丁基二甲基硅基缩酰亮氨酸甲酯酰基、亮氨酸甲酯酰基或--（CH2）n--COOR5（其中n是1-3的整数，R5是低级烷基基团），前提是R3与R4结合形成环戊基、环己基、四氢呋喃基或二氧杂环己基，这些环可选地被低级烷基、低级烯基、低级烷氧羰基基团或低级烷氧羰基甲基基团取代；当R1和R2一起取时，形成一个4-或5-成员碳环，该环可以被低级烷氧羰基基团或t-叔丁基二甲基硅氧羰基基团取代。
• Tertiary-butyldimethylsilyl carbamate derivative and process for producing the same
  申请人：SUNTORY LIMITED

  公开号：EP0217243A2

  公开（公告）日：1987-04-08

  At-butyldimethylsilyl carbamate derivative and a process for producing the same are disclosed. Tertiarybutyl- dimethylsilyl carbamate derivatives having the following general formula (1) are intermediates for the production of a variety of carbamate esters that can be extensively used as drugs acting on the central nervous system or circulatory organs, as agrichemicals (e.g. insecticides and herbicides), or as antimicrobial agents; a process capable of economical and efficient production of such intermediates is also disclosed: where R1 is an alkyl group having 1 - 3 carbon atoms or a hydrogen atom; R2 is (where R3 is a hydrogen atom, an alkyl, alkenyl or aralkyl group having 1 - 10 carbon atoms, each of which groups may be substituted by a hydroxyl group, a t-butyldimethylsilyloxy group, a methylthio group, a lower alkoxycarbonyl group, a lower alkoxy group, an indolyl group or an imidazolyl group; R4 is a lower alkoxycarbonyl group, an N-alkylamido group having 2 - 6 carbon atoms, an O-tetrahydropyranylthreonine methyl ester amido residue, an O-t-butyldimethyl- silylthreonine methyl ester amido residue, a threonine methyl ester amido residue or -(CH2)n-COOR5 (where n is an integer of 1 - 3 and R5 is a lower alkyl group), provided that R3 combines with R4 to form a cyclopentyl group, a cyclohexyl group, a tetrahydrofuranyl group or a dioxanyl group, these rings being optionally substituted by a lower alkyl group, a lower alkenyl group, a lower alkoxycarbonyl group or a lower alkoxycarbonylmethyl group); and R' and R2, when taken together, form a 4- or 5-membered carbon ring, which may be substituted by a lower alkoxycarbonyl group or a t-butyldimethylsilyloxycarbonyl group.

  本发明公开了叔丁基二甲基硅基氨基甲酸酯衍生物及其生产工艺。具有以下通式(1)的叔丁基二甲基硅基氨基甲酸酯衍生物是生产各种氨基甲酸酯的中间体，这些氨基甲酸酯可广泛用作作用于中枢神经系统或循环器官的药物、农用化学品（如杀虫剂和除草剂）或抗菌剂；还公开了一种能够经济、高效地生产这种中间体的工艺： 其中 R1 是具有 1 - 3 个碳原子的烷基或氢原子；R2 是 (其中 R3 是氢原子、具有 1-10 个碳原子的烷基、烯基或芳基，每个基团可被羟基、叔丁基二甲基硅氧基、甲硫基、低级烷氧基羰基、低级烷氧基、吲哚基或咪唑基取代；R4 是低级烷氧基羰基、具有 2-6 个碳原子的 N-烷基氨基、O-四氢吡喃苏氨酸甲酯氨基残基、O-叔丁基二甲基硅基苏氨酸甲酯氨基残基、苏氨酸甲酯氨基残基或-(CH2)n-COOR5（其中 n 为 1-3 的整数，R5 为低级烷基）、条件是 R3 与 R4 结合形成环戊基、环己基、四氢呋喃基或二噁烷基，这些环可选择被低级烷基、低级烯基、低级烷氧羰基或低级烷氧羰基甲基取代）；R'和 R2 合在一起形成一个 4 或 5 元碳环，可被一个低级烷氧羰基或一个 t-丁基二甲基硅氧基羰基取代。
• Pyrrolobenzodiazepine-anti-PSMA antibody conjugates
  申请人：MEDIMMUNE LIMITED

  公开号：US10736903B2

  公开（公告）日：2020-08-11

  Conjugates of an antibody that binds to PSMA with PBD dimers.

  与 PSMA 结合的抗体与 PBD 二聚体的共轭物。