(2R,3S,4S,5R,6S)-2-(乙酰氧基甲基)-6-(4-(羟甲基)-2-硝基苯氧基)四氢-2H-吡喃-3,4,5-三基三乙酸酯 | 290298-12-3

分子结构分类

有机化合物 - 有机氧化合物

中文名称

(2R,3S,4S,5R,6S)-2-(乙酰氧基甲基)-6-(4-(羟甲基)-2-硝基苯氧基)四氢-2H-吡喃-3,4,5-三基三乙酸酯

中文别名

——

英文名称

(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(4-(hydroxymethyl)-2-nitrophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

英文别名

[(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[4-(hydroxymethyl)-2-nitrophenoxy]oxan-2-yl]methyl acetate

(2R,3S,4S,5R,6S)-2-(乙酰氧基甲基)-6-(4-(羟甲基)-2-硝基苯氧基)四氢-2H-吡喃-3,4,5-三基三乙酸酯化学式

CAS

290298-12-3

化学式

C₂₁H₂₅NO₁₃

mdl

——

分子量

499.428

InChiKey

SUGKFMFBWQNBMQ-XDWAVFMPSA-N

BEILSTEIN

——

EINECS

——

物化性质

沸点：

612.9±55.0 °C(Predicted)
密度：

1.42±0.1 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

0.5
重原子数：

35
可旋转键数：

12
环数：

2.0
sp3杂化的碳原子比例：

0.52
拓扑面积：

190
氢给体数：

1
氢受体数：

13

上下游信息

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	2-nitro-4-(((((nitrophenoxy)carbonyl)oxy)methyl)phenoxy)peracyl-β-D-galactopyranoside	1188307-60-9	C₂₈H₂₈N₂O₁₇	664.534
——	(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(4-(6-hydroxy-11,11-dimethyl-3,9-dioxo-2,10-dioxa-4,8-diazadodecyl)-2-nitrophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate	1127247-19-1	C₃₀H₄₁N₃O₁₇	715.665
——	(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(4-((((4-mercaptophenyl)carbamoyl)oxy)methyl)-2-nitrophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate	1127247-15-7	C₂₈H₃₀N₂O₁₄S	650.617
——	(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(2-nitro-4-((trityloxy)methyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate	1127247-09-9	C₄₀H₃₉NO₁₃	741.749
——	(2S,3R,4S,5S,6R)-2-(4-(((1H-imidazole-1-carbonyl)oxy)methyl)-2-nitrophenoxy)-6-(acetoxymethyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate	959773-45-6	C₂₅H₂₇N₃O₁₄	593.501
——	(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(4-(6-(aminomethyl)-11-mercapto-3,8-dioxo-2,7-dioxa-4,9-diazaundecyl)-2-nitrophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate	1127247-22-6	C₂₈H₃₈N₄O₁₆S	718.693
——	(3-nitro-4-(((2S,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)methanol	1127246-99-4	C₄₁H₄₁NO₉	691.778
——	(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(4-(6-(((2-mercaptoethyl)carbamoyl)oxy)-11,11-dimethyl-3,9-dioxo-2,10-dioxa-4,8-diazadodecyl)-2-nitrophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate	1127247-21-5	C₃₃H₄₆N₄O₁₈S	818.81
——	3-nitro-4-(((2S,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)benzyl (4-nitrophenyl) carbonate	1127247-00-0	C₄₈H₄₄N₂O₁₃	856.883
——	(2S,3R,4S,5S,6R)-2-(4-(6-((1H-imidazole-1-carbonyl)oxy)-11,11-dimethyl-3,9-dioxo-2,10-dioxa-4,8-diazadodecyl)-2-nitrophenoxy)-6-(acetoxymethyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate	1127247-20-4	C₃₄H₄₃N₅O₁₈	809.738
——	(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(2-amino-4-((((4-mercaptophenyl)carbamoyl)oxy)methyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate	1127247-16-8	C₂₈H₃₂N₂O₁₂S	620.634
——	(2R,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(2-nitro-4-((trityloxy)methyl)phenoxy)tetrahydro-2H-pyran	1127247-10-2	C₆₀H₅₅NO₉	934.098
——	(2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-(2-nitro-4-((trityloxy)methyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triol	1127246-98-3	C₃₂H₃₁NO₉	573.599
——	3-nitro-4-(((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)benzyl (3-amino-2-(((2-mercaptoethyl)carbamoyl)oxy)propyl)carbamate	1127247-23-7	C₂₀H₃₀N₄O₁₂S	550.544
——	(3-nitro-4-(((2S,3R,4S,5S,6R)-3,4,5-tris((tert-butyldimethylsilyl)oxy)-6-(((tert-butyldimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)methanol	1127247-03-3	C₃₇H₇₃NO₉Si₄	788.33
——	3-nitro-4-(((2S,3R,4S,5S,6R)-3,4,5-tris((tert-butyldimethylsilyl)oxy)-6-(((tert-butyldimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)benzyl (4-nitrophenyl) carbonate	1127247-04-4	C₄₄H₇₆N₂O₁₃Si₄	953.435
——	(((2R,3S,4S,5R,6S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-6-(2-nitro-4-((trityloxy)methyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triyl)tris(oxy))tris(tert-butyldimethylsilane)	1127247-11-3	C₅₆H₈₇NO₉Si₄	1030.65
——	3-amino-4-(((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)benzyl (4-mercaptophenyl)carbamate	1127247-17-9	C₂₀H₂₄N₂O₈S	452.485
——	[2-amino-N-(4-β-D-2,3,4,6-tetra-O-acetylgalactopyranosyloxy-3-nitrophenyl)methoxycarbonyl-4-benzyloxy-5-methoxy-1,4-phenylene]carbonyl (2S)-pyrrolidine-2-carboxaldehyde diethyldithioacetal	1041181-51-4	C₄₆H₅₅N₃O₁₇S₂	986.085
——	3-nitro-4-(((2S,3R,4S,5S,6R)-3,4,5-tris((tert-butyldimethylsilyl)oxy)-6-(((tert-butyldimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)benzyl (3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-hydroxypropyl)(methyl)carbamate	1127247-05-5	C₅₇H₉₃N₃O₁₃Si₄	1140.72
——	(11S)-10-(4-beta-D-2,3,4,6-tetra-O-acetyl-galactopyranosyloxy-3-nitro-phenyl)methoxycarbonyl-11-hydroxy-7-methoxy-1,2,3,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one	1041181-54-7	C₄₂H₄₅N₃O₁₈	879.829
——	[(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[4-[[(2S,3S,4S,6R)-6-[[(1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-2,4-dihydro-1H-tetracen-1-yl]oxy]-3-hydroxy-2-methyloxan-4-yl]carbamoyloxymethyl]-2-nitrophenoxy]oxan-2-yl]methyl acetate	290304-25-5	C₄₉H₅₂N₂O₂₄	1052.95
——	(11S)-10-(4-β-D-galactopyranosyloxy-3-nitro-phenyl)methoxycarbonyl-11-hydroxy-7-methoxy-1,2,3,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one	1041181-56-9	C₃₄H₃₇N₃O₁₄	711.679
(8S,10S)-8-乙酰基-7,8,9,10-四氢-6,8,11-三羟基-1-甲氧基-10-[[2,3,6-三脱氧-3-[[[[4-(beta-D-吡喃半乳糖基氧基)-3-硝基苯基]甲氧基]羰基]氨基]-alpha-L-来苏-己糖吡喃糖苷]氧基]-5,12-并四苯醌	[3-Nitro-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methyl N-[(2S,3S,4S,6R)-6-[[(1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-2,4-dihydro-1H-tetracen-1-yl]oxy]-3-hydroxy-2-methyloxan-4-yl]carbamate	290304-24-4	C₄₁H₄₄N₂O₂₀	884.802

反应信息

作为反应物：

描述：

(2R,3S,4S,5R,6S)-2-(乙酰氧基甲基)-6-(4-(羟甲基)-2-硝基苯氧基)四氢-2H-吡喃-3,4,5-三基三乙酸酯在 4-二甲氨基吡啶作用下，以二氯甲烷、 N,N-二甲基甲酰胺为溶剂，反应 26.17h，生成 (2S,3R,4S,5S,6R)-2-(4-(6-((1H-imidazole-1-carbonyl)oxy)-11,11-dimethyl-3,9-dioxo-2,10-dioxa-4,8-diazadodecyl)-2-nitrophenoxy)-6-(acetoxymethyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

参考文献：

名称：

Saccharidic fluorescent substrates, their process of preparation and their use

摘要：

本发明涉及一种具有自裂解间隔臂的荧光酶底物，其为糖类性质，通过荧光团F和至少一种抑制F荧光的抑制剂进行功能化，以及将其用于制备体内功能成像的诊断试剂的用途，以及包含至少一种这种酶底物的功能成像诊断试剂。

公开号：

US08076466B2
作为产物：

描述：

2,3,4,6-四乙酰氧基-alpha-D-吡喃糖溴化物在苄基三乙基氯化铵、 silica gel 、 sodium hydroxide 作用下，以二氯甲烷、氯仿、异丙醇为溶剂，反应 3.5h，生成 (2R,3S,4S,5R,6S)-2-(乙酰氧基甲基)-6-(4-(羟甲基)-2-硝基苯氧基)四氢-2H-吡喃-3,4,5-三基三乙酸酯

参考文献：

名称：

特定酶触发释放时糖基化治疗诊断前药的实时多光子跟踪和生物成像

摘要：

已经开发了糖基化治疗诊断前药，其中治疗成分通过特定糖苷酶的作用在糖苷键的酶激活时经历触发释放，从而导致治疗性货物的选择性递送，这是通过实时生物成像观察到的过程。

DOI：

10.1002/chem.202103858

点击查看最新优质反应信息

文献信息

ANTI-EGFR ANTIBODY DRUG CONJUGATES

申请人：AbbVie Inc.

公开号：US20190153107A1

公开（公告）日：2019-05-23

The invention relates to anti-Epidermal Growth Factor Receptor (EGFR) antibody drug conjugates (ADCs) which inhibit Bcl-xL, including compositions and methods of using said ADCs.

这项发明涉及抑制Bcl-xL的抗表皮生长因子受体（EGFR）抗体药物结合物（ADCs），包括使用所述ADCs的组合物和方法。
ANTI-B7-H3 ANTIBODIES AND ANTIBODY DRUG CONJUGATES

申请人：AbbVie Inc.

公开号：US20170355769A1

公开（公告）日：2017-12-14

The invention relates to B7 homology 3 protein (B7-H3) antibodies and antibody drug conjugates (ADCs), including compositions and methods of using said antibodies and ADCs.

这项发明涉及B7同源物3蛋白（B7-H3）抗体和抗体药物结合物（ADCs），包括使用所述抗体和ADCs的组合物和方法。
BCL-XL Inhibitory Compounds and Antibody Drug Conjugates Including the Same

申请人：Ackler Scott L.

公开号：US20160158377A1

公开（公告）日：2016-06-09

Small molecule Bcl-xL inhibitors and Antibody Drug Conjugates (ADCs) comprising small molecule Bcl-xL inhibitors are disclosed herein. The Bcl-xL inhibitors and ADCs of the disclosure are useful for, among other things, inhibiting anti-apoptotic Bcl-xL proteins as a therapeutic approach towards the treatment of diseases that involve a dysregulated apoptosis pathway.

小分子Bcl-xL抑制剂和包括小分子Bcl-xL抑制剂的抗体药物结合物（ADCs）在此披露。披露的Bcl-xL抑制剂和ADCs可用于抑制抗凋亡Bcl-xL蛋白，作为治疗涉及失调凋亡途径的疾病的治疗方法之一。
[EN] ANTI-EGFR ANTIBODY DRUG CONJUGATES<br/>[FR] CONJUGUÉ ANTICORPS-MÉDICAMENT ANTI-EGFR

申请人：ABBVIE INC

公开号：WO2017214282A1

公开（公告）日：2017-12-14

The invention relates to anti-Epidermal Growth Factor Receptor (EGFR) antibody drug conjugates (ADCs) which inhibit Bcl-xL, including compositions and methods of using said ADCs. Formula (IIa), (IIb), (IIc)

本发明涉及抑制Bcl-xL的抗表皮生长因子受体（EGFR）抗体药物偶联物（ADCs），包括所述ADCs的组成和方法。公式（IIa），（IIb），（IIc）
[EN] ANTIBODY DRUG CONJUGATES WITH CELL PERMEABLE BCL-XL INHIBITORS<br/>[FR] CONJUGUÉS ANTICORPS MÉDICAMENTS AVEC DES INHIBITEURS BCL-XL À PERMÉABILITÉ CELLULAIRE

申请人：ABBVIE INC

公开号：WO2016094505A1

公开（公告）日：2016-06-16

Small molecule Bcl-xL inhibitors and Antibody Drug Conjugates (ADCs) comprising small molecule Bcl-xL inhibitors are disclosed herein. The Bcl-xL inhibitors and ADCs of the disclosure are useful for, among other things, inhibiting anti-apoptotic Bcl xL proteins as a therapeutic approach towards the treatment of diseases that involve a dysregulated apoptosis pathway.

本文披露了小分子Bcl-xL抑制剂和包含小分子Bcl-xL抑制剂的抗体药物结合物（ADCs）。本公开的Bcl-xL抑制剂和ADCs可用于抑制抗凋亡Bcl-xL蛋白，作为治疗涉及失调凋亡途径的疾病的治疗方法之一。