(3aS,4S,6R,6aR)-tert-butyl 4-(4-amino-5-(ethoxycarbonyl)-1H-pyrrol-3-yl)-6-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyldihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-5(4H)-carboxylate | 284490-15-9

分子结构分类

有机化合物 - 有机杂环化合物 - 吡咯烷类

中文名称

——

中文别名

——

英文名称

(3aS,4S,6R,6aR)-tert-butyl 4-(4-amino-5-(ethoxycarbonyl)-1H-pyrrol-3-yl)-6-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyldihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-5(4H)-carboxylate

英文别名

tert-butyl (3aS,4S,6R,6aR)-4-(4-amino-5-ethoxycarbonyl-1H-pyrrol-3-yl)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate

(3aS,4S,6R,6aR)-tert-butyl 4-(4-amino-5-(ethoxycarbonyl)-1H-pyrrol-3-yl)-6-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyldihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-5(4H)-carboxylate化学式

CAS

284490-15-9

化学式

C₂₆H₄₅N₃O₇Si

mdl

——

分子量

539.745

InChiKey

PXVFGOAJKXUJHV-RCOXNQKVSA-N

BEILSTEIN

——

EINECS

——

物化性质

沸点：

602.1±55.0 °C(Predicted)
密度：

1.117±0.06 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

4.98
重原子数：

37
可旋转键数：

10
环数：

3.0
sp3杂化的碳原子比例：

0.77
拓扑面积：

125
氢给体数：

2
氢受体数：

8

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
b-D-半乳吡喃糖,1,6-脱水-,3-乙酸酯2-[二(苯基甲基)磷酸酯](9CI)	(1S)-1-(3-amino-N-benzyloxycarbonyl-2-ethoxycarbonylpyrrol-4-yl)-N-tert-butoxycarbonyl-5-O-tert-butyldimethylsilyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol	222631-12-1	C₃₄H₅₁N₃O₉Si	673.879
噻吩并[2,3-b]吡啶,2,3-二氢-6-甲基-4-苯基-	N-tert-butoxycarbonyl-7-O-tert-butyldimethylsilyl-2-cyano-1,2,3,6-tetradeoxy-1-N-(ethoxycarbonylmethylamino)-3,6-imino-4,5-O-isopropylidene-D-allo-hept-1-enitol	222631-11-0	C₂₆H₄₅N₃O₇Si	539.745
——	(1S)-N-tert-butoxycarbonyl-5-O-tert-butyldimethylsilyl-1-C-(1-cyano-2-hydroxyethenyl)-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol	284490-14-8	C₂₂H₃₈N₂O₆Si	454.639
4-氨基-3,6-二[[4-[(2,4-二氨基苯基)偶氮]苯基]偶氮]-5-羟基萘-2,7-二磺基酸,盐锂钠	(3aR,4R,6S,6aS)-tert-butyl 4-(((tert-butyldimethylsilyl)oxy)methyl)-6-((E/Z)-1-cyano-2-hydroxyvinyl)-2,2-dimethyldihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-5(4H)-carboxylate	222631-10-9	C₂₂H₃₈N₂O₆Si	454.639
2-[2-[[5-亚氨基-3-甲基-1-(8-磺酸根-2-萘基)-4H-吡唑-4-基]偶氮]-5-[4-[[5-亚氨基-3-甲基-1-(8-磺酸根-2-萘基)-4H-吡唑-4-基]偶氮]-3-(2-羟基-2-羰基-乙氧基)苯基]苯氧基]乙酸四钠	N-tert-butoxycarbonyl-7-O-tert-butyldimethylsilyl-2,3,6-trideoxy-3,6-imino-4,5-O-isopropylidene-D-allo-heptononitrile	222631-09-6	C₂₁H₃₈N₂O₅Si	426.629
(3AR,4R,6AS)-5-苄基-4-(((叔丁基二甲基硅烷基)氧基)甲基)-2,2-二甲基四	5-O-tert-butyldimethylsilyl-1,4-N-benzylimino-2,3-O-isopropylidene-D-ribitol	153172-30-6	C₂₁H₃₅NO₃Si	377.599

下游产品

中文名称	英文名称	CAS号	化学式	分子量
噁丙环,甲基-,聚合噁丙环,单辛基醚,磷酸酯	(1S)-1-[3-(N-benzoyl-S-methylisothiocarbamoyl)imino-2-ethoxycarbonylpyrrol-4-yl]-N-tert-butoxycarbonyl-5-O-tert-butyldimethylsilyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol	222631-14-3	C₃₅H₅₂N₄O₈SSi	716.971
2(3H)-噻唑亚胺,3-乙基-4-甲基-	(1S)-N-tert-butoxycarbonyl-5-O-tert-butyldimethylsilyl-1-(9-deazahypoxanthin-9-yl)-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol	222631-13-2	C₂₅H₄₀N₄O₆Si	520.701
——	(3aS,4S,6R,6aR)-tert-butyl 4-(2-amino-4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-7-yl)-6-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyldihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-5(4H)-carboxylate	1610426-20-4	C₂₅H₄₁N₅O₆Si	535.716
——	(1S)-1-(9-deazaguanidin-9-yl)-N-tert-butoxycarbonyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol	284490-16-0	C₁₉H₂₇N₅O₆	421.453
7-[(2S,3S,4R,5R)-3,4-二羟基-5-(羟甲基)-2-吡咯烷基]-3,5-二氢-4H-吡咯并[3,2-D]嘧啶-4-酮	forodesine	209799-67-7	C₁₁H₁₄N₄O₄	266.257

反应信息

作为反应物：

描述：

(3aS,4S,6R,6aR)-tert-butyl 4-(4-amino-5-(ethoxycarbonyl)-1H-pyrrol-3-yl)-6-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyldihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-5(4H)-carboxylate 在三氟乙酸作用下，以乙醇为溶剂，反应 16.0h，生成 7-[(2S,3S,4R,5R)-3,4-二羟基-5-(羟甲基)-2-吡咯烷基]-3,5-二氢-4H-吡咯并[3,2-D]嘧啶-4-酮

参考文献：

名称：

Synthesis of Transition State Analogue Inhibitors for Purine Nucleoside Phosphorylase and N-Riboside Hydrolases

摘要：

Syntheses of the 'Immucillins', potent aza-C-nncleoside inhibitors of purine nucleoside phosphorylase are reported as well as those of 5-deoxy-, 5-deoxyfluoro- and 2-deoxy- analogues and others having modified bases. (C) 2000 Elsevier Science Ltd. All rights reserved.

DOI：

10.1016/s0040-4020(00)00194-0
作为产物：

描述：

2,3-O-异亚丙基-D-核糖酸 gamma-内酯在吡啶、咪唑、甲醇、 4-二甲氨基吡啶、 selenium(IV) oxide 、 sodium tetrahydroborate 、正丁基锂、 palladium 10% on activated carbon 、 palladium on activated charcoal 、水、氢气、双氧水、 sodium acetate 、溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯、 potassium hydroxide 、锌作用下，以四氢呋喃、甲醇、乙醇、二氯甲烷、氯仿、 N,N-二甲基甲酰胺、丙酮为溶剂， -78.0~70.0 ℃ 、551.59 kPa 条件下，反应 148.5h，生成 (3aS,4S,6R,6aR)-tert-butyl 4-(4-amino-5-(ethoxycarbonyl)-1H-pyrrol-3-yl)-6-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyldihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-5(4H)-carboxylate

参考文献：

名称：

[EN] ANTIVIRAL AZASUGAR-CONTAINING NUCLEOSIDES
[FR] NUCLÉOSIDES ANTIVIRAUX CONTENANT DE L'AZASUCRE

摘要：

公开号：

WO2014078778A3

点击查看最新优质反应信息

文献信息

ANTIVIRAL AZASUGAR-CONTAINING NUCLEOSIDES

申请人：BIOCRYST PHARMACEUTICALS, INC.

公开号：US20150291596A1

公开（公告）日：2015-10-15

Disclosed are compounds comprising an azasugar attached to a heterocyclic base, including pharmaceutically acceptable salts thereof, suitable for use in inhibiting viral RNA polymerase activity or viral replication, and treating viral infections. The compounds are characterized, in part, by favorable pharmacokinetics for the active pharmaceutical ingredient, particularly in conjunction with enteral administration, including, in particular, oral administration. Also disclosed are pharmaceutical compositions comprising one or more compounds mentioned above, or pharmaceutically acceptable salts thereof, as well as methods for preparing same. Also provided are methods for inhibiting viral RNA polymerase activity, viral replication, and treating viral infections.

本发明涉及一种含有偶氮糖与杂环碱基结合的化合物，包括其药学上可接受的盐，适用于抑制病毒RNA聚合酶活性或病毒复制，并用于治疗病毒感染。该化合物的特点之一是具有良好的药代动力学，特别是在肠道给药的情况下，包括口服给药。本发明还涉及含有上述一种或多种化合物或其药学上可接受的盐的制药组合物，以及制备它们的方法。本发明还提供了抑制病毒RNA聚合酶活性、病毒复制和治疗病毒感染的方法。
[EN] ANTIVIRAL AZASUGAR-CONTAINING NUCLEOSIDES<br/>[FR] NUCLÉOSIDES ANTIVIRAUX CONTENANT DE L'AZASUCRE

申请人：BIOCRYST PHARM INC

公开号：WO2014078778A3

公开（公告）日：2014-10-09
Synthesis of Transition State Analogue Inhibitors for Purine Nucleoside Phosphorylase and N-Riboside Hydrolases

作者：Gary B. Evans、Richard H. Furneaux、Graeme J. Gainsford、Vern L. Schramm、Peter C. Tyler

DOI：10.1016/s0040-4020(00)00194-0

日期：2000.5

Syntheses of the 'Immucillins', potent aza-C-nncleoside inhibitors of purine nucleoside phosphorylase are reported as well as those of 5-deoxy-, 5-deoxyfluoro- and 2-deoxy- analogues and others having modified bases. (C) 2000 Elsevier Science Ltd. All rights reserved.