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O-tert-Butyl-N-(9-fluorenylmethoxycarbonyl)-L-threonin-benzylester | 73724-49-9

分子结构分类

有机化合物 - 苯类化合物 - 芴

中文名称

——

中文别名

——

英文名称

O-tert-Butyl-N-(9-fluorenylmethoxycarbonyl)-L-threonin-benzylester

英文别名

benzyl N-(((9H-fluoren-9-yl)methoxy)carbonyl)-O-(tert-butyl)-L-threoninate；O-(1,1-Dimethylethyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-threonine phenylmethyl ester；benzyl (2S,3R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[(2-methylpropan-2-yl)oxy]butanoate

O-tert-Butyl-N-(9-fluorenylmethoxycarbonyl)-L-threonin-benzylester化学式

CAS

73724-49-9

化学式

C₃₀H₃₃NO₅

mdl

——

分子量

487.596

InChiKey

KGRDAMFCJAHXEG-HRFSGMKKSA-N

BEILSTEIN

——

EINECS

——

物化性质

沸点：

652.0±55.0 °C(Predicted)
密度：

1.166±0.06 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

5.84
重原子数：

36.0
可旋转键数：

8.0
环数：

4.0
sp3杂化的碳原子比例：

0.33
拓扑面积：

73.86
氢给体数：

1.0
氢受体数：

5.0

上下游信息

上游原料

中文名称	英文名称	CAS号	化学式	分子量
Fmoc-O-叔丁基-L-苏氨酸	Fmoc-Thr(tBu)-OH	71989-35-0	C₂₃H₂₇NO₅	397.471

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	Nε-(tert-Butoxycarbonyl)-Nα-(9-fluorenylmethoxycarbonyl)-L-lysyl-O-tert-butyl-L-threonin-benzylester	120792-05-4	C₄₁H₅₃N₃O₈	715.887
——	Nε-(tert-Butoxycarbonyl)-Nα-(9-fluorenylmethoxycarbonyl)-L-lysyl-Nε-(tert-butoxycarbonyl)-L-lysyl-O-tert-butyl-L-threonin-benzylester	120792-07-6	C₅₂H₇₃N₅O₁₁	944.179
——	O-tert-Butyl-N-(9-fluorenylmethoxycarbonyl)-L-threonyl-Nε-(tert-butoxycarbonyl)-L-lysyl-Nε-(tert-butoxycarbonyl)-L-lysyl-O-tert-butyl-L-threonin-benzylester	120792-09-8	C₆₀H₈₈N₆O₁₃	1101.39
——	O-tert-Butyl-N-(9-fluorenylmethoxycarbonyl)-L-seryl-O-tert-butyl-L-threonyl-Nε-(tert-butoxycarbonyl)-L-lysyl-Nε-(tert-butoxycarbonyl)-L-lysyl-O-tert-butyl-L-threonin-benzylester	120792-11-2	C₆₇H₁₀₁N₇O₁₅	1244.58
——	benzyl O-(tert-butyl)-N-((4-nitrophenoxy)carbonyl)-L-threoninate	1454708-62-3	C₂₂H₂₆N₂O₇	430.458
——	(2S,3R)-2-((S)-2-Amino-6-tert-butoxycarbonylamino-hexanoylamino)-3-tert-butoxy-butyric acid benzyl ester	120792-06-5	C₂₆H₄₃N₃O₆	493.644
——	(2S,3R)-2-[(S)-2-((S)-2-Amino-6-tert-butoxycarbonylamino-hexanoylamino)-6-tert-butoxycarbonylamino-hexanoylamino]-3-tert-butoxy-butyric acid benzyl ester	120792-08-7	C₃₇H₆₃N₅O₉	721.935
——	(2S,3R)-2-{(S)-2-[(S)-2-((2S,3R)-2-Amino-3-tert-butoxy-butyrylamino)-6-tert-butoxycarbonylamino-hexanoylamino]-6-tert-butoxycarbonylamino-hexanoylamino}-3-tert-butoxy-butyric acid benzyl ester	120792-10-1	C₄₅H₇₈N₆O₁₁	879.148
——	(2S,3R)-2-((S)-2-{(S)-2-[(2S,3R)-2-((S)-2-Amino-3-tert-butoxy-propionylamino)-3-tert-butoxy-butyrylamino]-6-tert-butoxycarbonylamino-hexanoylamino}-6-tert-butoxycarbonylamino-hexanoylamino)-3-tert-butoxy-butyric acid benzyl ester	120829-07-4	C₅₂H₉₁N₇O₁₃	1022.33
——	benzyl N-(((S)-1-(2-(N-(tert-butoxycarbonyl)-O-(tert-butyl)-L-seryl)hydrazineyl)-1,4-dioxo-4-(tritylamino)butan-2-yl)carbamoyl)-O-(tert-butyl)-L-threoninate	1454708-63-4	C₅₁H₆₆N₆O₁₀	923.119
——	benzyl N-(((S)-4-amino-1-(2-(N-(tert-butoxycarbonyl)-O-(tert-butyl)-L-seryl)hydrazineyl)-1,4-dioxobutan-2-yl)carbamoyl)-O-(tert-butyl)-L-threoninate	1454708-67-8	C₃₂H₅₂N₆O₁₀	680.799

反应信息

作为反应物：

描述：

O-tert-Butyl-N-(9-fluorenylmethoxycarbonyl)-L-threonin-benzylester 在 palladium on activated charcoal 哌啶、四丁基氟化铵、氢气、 potassium carbonate 、 1-羟基苯并三唑、 N,N-二异丙基乙胺、 N,N'-二环己基碳二亚胺作用下，以四氢呋喃、甲醇、二氯甲烷、 N,N-二甲基甲酰胺为溶剂， 23.0 ℃ 、101.33 kPa 条件下，反应 14.33h，生成 (2S,3S)-2-[(2S,3S)-2-(Acetyl-methyl-amino)-3-methyl-pentanoylamino]-3-methyl-pentanoic acid {(1S,2R)-2-tert-butoxy-1-[(S)-3-methyl-1-((R)-2-methyl-oxiranecarbonyl)-butylcarbamoyl]-propyl}-amide

参考文献：

名称：

全合成中的螺二环氧化物：Epoxomicin

摘要：

描述了螺二环氧化物官能团在全合成中的首次使用，该研究最终以有效合成有效的蛋白酶体抑制剂环氧霉素为高潮。通过氧化从丙二烯衍生的螺二环氧化物显示出顺式双取代酮及其衍生物，包括原酸酯、恶唑啉、叠氮环氧化物以及含磺酰胺、酰胺和叠氮化物的羟基酮。

DOI：

10.1021/ja044563c
作为产物：

描述：

溴甲苯、 Fmoc-O-叔丁基-L-苏氨酸在甲基三辛基氯化铵、碳酸氢钠作用下，以二氯甲烷、水为溶剂，反应 11.0h，生成 O-tert-Butyl-N-(9-fluorenylmethoxycarbonyl)-L-threonin-benzylester

参考文献：

名称：

使用氨基酸的 Bn 或 BcM 酯合成原子经济的逆固相肽

摘要：

据报道，一种原子经济的 N 到 C 定向的固相肽合成，使用氨基酸的苄基 (Bn) 或 (二苯甲基-氨基甲酰基)-甲基 (BcM) 酯作为构建单元，促进高效肼解，方便转化为酰基叠氮化物，并与下一个氨基酸酯进行稳健的酰胺化。该方法无需偶联试剂，对侧链OH、CO 2 H、CONH2等无保护，因此与基于BOC或Fmoc的C-to-N-相比，原子经济性显着提高定向方法。

DOI：

10.1021/acs.orglett.1c02769

点击查看最新优质反应信息

文献信息

PEPTIDOMIMETIC COMPOUNDS AS IMMUNOMODULATORS

申请人：AURIGENE DISCOVERY TECHNOLOGIES LIMITED

公开号：US20130237580A1

公开（公告）日：2013-09-12

The present invention relates to novel peptidomimetic compounds as therapeutic agents capable of inhibiting the programmed cell death 1 (PD1) signalling pathway. The invention also relates to derivatives of the therapeutic agents. The invention also encompasses the use of the said therapeutic agents and derivatives for treatment of disorders via immunopotentiation comprising inhibition of immunosuppressive signal induced due to PD-1, PD-L1, or PD-L2 and therapies using them.

本发明涉及作为治疗剂的新型肽类似物化合物，能够抑制程序性细胞死亡1（PD1）信号通路。该发明还涉及这些治疗剂的衍生物。该发明还包括利用所述治疗剂和衍生物治疗通过免疫增强来抑制由于PD-1、PD-L1或PD-L2引起的免疫抑制信号的障碍，并使用它们进行治疗的疗法。
Influence of steric parameters on the synthesis of tetramates from α-amino-β-alkoxy-esters and Ph3PCCO

作者：Inga Loke、Natja Park、Karl Kempf、Carsten Jagusch、Rainer Schobert、Sabine Laschat

DOI：10.1016/j.tet.2011.10.099

日期：2012.1

alpha-Aminoesters react with Ph3PCCO in a domino addition-Wittig cyclization sequence affording enantiomerically pure tetramates. In the case of beta-oxo functionalized alpha-aminoesters, e.g., esters of serine, threonine or beta-hydroxyornithine the yields of this reaction depend heavily on the bulkiness of the beta-OR group and on the configuration of beta-carbon atom C-3. Smaller residues and 2R/3R-configured aminoesters give better yields. The alkoxycarbonyl group of the ester moiety and the residue on the N-atom are less important. These findings can be accounted for by assuming an early puckered transition state for the intramolecular ring-closing Wittig reaction. The addition of sub-stoichiometric amounts of benzoic acid or N-hydroxysuccinimide (for acid-sensitive compounds) is advantageous in some cases as it accelerates the formation of the intermediate amide ylides. (C) 2011 Elsevier Ltd. All rights reserved.
Paulsen, Hans; Adermann, Knut, Liebigs Annalen der Chemie, 1989, p. 751 - 770

作者：Paulsen, Hans、Adermann, Knut

DOI：——

日期：——
<i>In Vitro</i> Assessment of Putative PD-1/PD-L1 Inhibitors: Suggestions of an Alternative Mode of Action

作者：Derek J. Blevins、Ronan Hanley、Trevor Bolduc、David A. Powell、Michael Gignac、Kayleigh Walker、Mark D. Carr、Fraser Hof、Jeremy E. Wulff

DOI：10.1021/acsmedchemlett.9b00221

日期：2019.8.8

The programmed cell death protein 1 (PD-1) signaling axis is among the most important therapeutic targets in modern oncology. Aurigene Discovery Technologies Ltd. (Aurigene) has patented a series of peptidomimetic small molecules derived from the PD-1 protein sequence for use in targeting the interaction between PD-1 and its ligand, PD-L1. We evaluated three of Aurigenes most potent compounds in SPR binding assays. Our results showed that these compounds-each of which is known to be potently effective in a splenocyte recovery assay-do not directly inhibit the PD-1/PD-L1 interaction nor do they appear to bind to either of the constituent proteins, indicating that another mechanism is at play. As a result of these studies and upon consideration of structural features within the PD-1/PD-L1 complex, we hypothesize that the Aurigene molecules may interact with a currently unknown protein capable of regulating the PD-1 axis.