benzyl N-[9-(fluorenylmethoxycarbonyl)]-D-threoninate | 337903-38-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: benzyl N-[9-(fluorenylmethoxycarbonyl)]-D-threoninate
• 英文别名: N-fluorenylmethoxycarbonyl-D-threonine benzyl ester；N-((9H-fluoren-9yl)methoxycarbonyl)-D-threonine benzyl ester；N-Fmoc-D-threonine benzyl ester；benzyl (2R,3S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hydroxybutanoate
• CAS: 337903-38-5
• 化学式: C₂₆H₂₅NO₅
• 分子量: 431.488
• InChiKey: WQYIETDVEJEHCP-BXKMTCNYSA-N

物化性质

• 沸点：
  656.9±55.0 °C(Predicted)
• 密度：
  1.257±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 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：

  benzyl N-[9-(fluorenylmethoxycarbonyl)]-D-threoninate 在 哌啶 、 吡啶 、 甲酸 、 palladium 10% on activated carbon 、 silver perchlorate 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.25h， 生成 Fmoc-D-Thr(Ac₃GalNAcα)-Pro-Gly-Hex-OH
  参考文献：
  名称：

  Divergent Behavior of Glycosylated Threonine and Serine Derivatives in Solid Phase Peptide Synthesis

  摘要：

  Solid phase peptide coupling of glycosylated threonlne derivatives was systematically evaluated. In contrast to glycosylated serine derivatives which are highly prone to epimerization, glycosylated threonine derivatives produce only negligible amounts of epimerization. Under forcing conditions, glycosylated threonine analogs undergo beta-elimination, rather than epimerization. Mechanistic studies and molecular modeling were used to understand the origin of the differences in reactivity.

  DOI：

  10.1021/ol301723e
• 作为产物：
  描述：

  D-threonine-O-tert-butyl-N-FMOC benzyl ester 在 三氟乙酸 作用下， 反应 2.0h， 以92%的产率得到benzyl N-[9-(fluorenylmethoxycarbonyl)]-D-threoninate
  参考文献：
  名称：

  Solid-Phase Synthesis of O-Linked Glycopeptide Analogues of Enkephalin

  摘要：

  The synthesis of 18 N-alpha -FMOC-amino acid glycosides for solid-phase glycopeptide assembly is reported. The glycosides were synthesized either from the corresponding O'Donnell Schiff bases or from N-alpha -FMOC-amino protected serine or threonine and the appropriate glycosyl bromide using Hanessian's modification of the Koenigs-Knorr reaction. Reaction rates of D-glycosyl bromides (e.g., acetobromoglucose) with the L- and D-forms of serine and threonine are distinctly different and can be rationalized in terms of the steric interactions within the two types of diastereomeric transition states for the D/L and D/D reactant pairs. The N-alpha -FMOC-protected glycosides [monosaccharides Xyl, Glc, Gal, Man, GlcNAc, and GalNAc; disaccharides Gal-beta (1-4)-Gle (lactose), Glc-beta-(1-4)-Glc (cellobiose), and Gal-alpha (1-6)-Glc (melibiose)] were incorporated into 22 enkephalin glycopeptide analogues. These peptide opiates bearing the pharmacophore H-Tyr-c[DCys-Gly-PheDCys]- were designed to probe the significance of the glycoside moiety and the carbohydrate-peptide linkage region in blood-brain barrier (BBB) transport, opiate receptor binding, and analgesia.

  DOI：

  10.1021/jo005712m

文献信息

• [EN] 2-ARYLSULFONAMIDO-N-ARYLACETAMIDE DERIVATIZED STAT3 INHIBITORS<br/>[FR] INHIBITEURS DE STAT3 DÉRIVÉS DE 2-ARYLSULFONAMIDO-N-ARYLACÉTAMIDE
  申请人：UNIV HAWAII

  公开号：WO2018136935A1

  公开（公告）日：2018-07-26

  The present disclosure provides pharmaceutical compositions comprising 2-arylsulfonamido-N-arylacetamide derivatized Stat3 inhibitors and certain pharmaceutically acceptable salts thereof, and methods of their use.

  本公开提供了含有2-芳基磺酰胺基-N-芳基乙酰胺衍生的Stat3抑制剂及其某些药用盐的制药组合物，以及它们的使用方法。
• 一种N-芴甲氧羰基-O-辛酰基-丝/苏氨酸的制备方法
  申请人：吉尔生化（上海）有限公司

  公开号：CN109627185A

  公开（公告）日：2019-04-16

  本发明涉及一种N‑芴甲氧羰基‑O‑辛酰基‑丝/苏氨酸的制备方法，主要解决现有合成方法的操作难度大，且难以提纯以及放大生产中不环保的技术问题。本发明的技术方案为：一种N‑芴甲氧羰基‑O‑辛酰基‑丝/苏氨酸的制备方法，包括以下步骤：由N‑芴甲氧羰基‑丝/苏氨酸‑苄酯为起始原料，与正辛酸通过加入缩合剂进行缩合反应，得到N‑芴甲氧羰基–O‑辛酰基‑丝/苏氨酸‑苄酯，经过纯化，将N‑芴甲氧羰基–O‑辛酰基‑丝/苏氨酸‑苄酯加入脱苄基试剂通过钯炭氢化去苄基，得到N‑芴甲氧羰基–O‑辛酰基‑丝/苏氨酸‑苄酯。本发明的产物在多肽药物领域有重要应用。
• Solid-Phase Synthesis of O-Linked Glycopeptide Analogues of Enkephalin
  作者：Scott A. Mitchell、Matt R. Pratt、Victor J. Hruby、Robin Polt

  DOI：10.1021/jo005712m

  日期：2001.4.1

  The synthesis of 18 N-alpha -FMOC-amino acid glycosides for solid-phase glycopeptide assembly is reported. The glycosides were synthesized either from the corresponding O'Donnell Schiff bases or from N-alpha -FMOC-amino protected serine or threonine and the appropriate glycosyl bromide using Hanessian's modification of the Koenigs-Knorr reaction. Reaction rates of D-glycosyl bromides (e.g., acetobromoglucose) with the L- and D-forms of serine and threonine are distinctly different and can be rationalized in terms of the steric interactions within the two types of diastereomeric transition states for the D/L and D/D reactant pairs. The N-alpha -FMOC-protected glycosides [monosaccharides Xyl, Glc, Gal, Man, GlcNAc, and GalNAc; disaccharides Gal-beta (1-4)-Gle (lactose), Glc-beta-(1-4)-Glc (cellobiose), and Gal-alpha (1-6)-Glc (melibiose)] were incorporated into 22 enkephalin glycopeptide analogues. These peptide opiates bearing the pharmacophore H-Tyr-c[DCys-Gly-PheDCys]- were designed to probe the significance of the glycoside moiety and the carbohydrate-peptide linkage region in blood-brain barrier (BBB) transport, opiate receptor binding, and analgesia.
• Divergent Behavior of Glycosylated Threonine and Serine Derivatives in Solid Phase Peptide Synthesis
  作者：Yalong Zhang、Saddam M. Muthana、Joseph J. Barchi、Jeffrey C. Gildersleeve

  DOI：10.1021/ol301723e

  日期：2012.8.3

  Solid phase peptide coupling of glycosylated threonlne derivatives was systematically evaluated. In contrast to glycosylated serine derivatives which are highly prone to epimerization, glycosylated threonine derivatives produce only negligible amounts of epimerization. Under forcing conditions, glycosylated threonine analogs undergo beta-elimination, rather than epimerization. Mechanistic studies and molecular modeling were used to understand the origin of the differences in reactivity.