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(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 | 153172-30-6

分子结构分类

有机化合物 - 苯类化合物 - 苯和取代衍生物

中文名称

(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

中文别名

——

英文名称

5-O-tert-butyldimethylsilyl-1,4-N-benzylimino-2,3-O-isopropylidene-D-ribitol

英文别名

4H-1,3-Dioxolo[4,5-c]pyrrole, 4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]tetrahydro-2,2-dimethyl-5-(phenylmethyl)-, (3aR,4R,6aS)-；[(3aR,4R,6aS)-5-benzyl-2,2-dimethyl-3a,4,6,6a-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl]methoxy-tert-butyl-dimethylsilane

(3AR,4R,6AS)-5-苄基-4-(((叔丁基二甲基硅烷基)氧基)甲基)-2,2-二甲基四化学式

CAS

153172-30-6

化学式

C₂₁H₃₅NO₃Si

mdl

——

分子量

377.599

InChiKey

QQIXCHPHMBTTIZ-CEXWTWQISA-N

BEILSTEIN

——

EINECS

——

物化性质

沸点：

425.2±35.0 °C(Predicted)
密度：

1.006±0.06 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

4.41
重原子数：

26
可旋转键数：

6
环数：

3.0
sp3杂化的碳原子比例：

0.71
拓扑面积：

30.9
氢给体数：

0
氢受体数：

4

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
——	N-benzyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol	117858-84-1	C₁₅H₂₁NO₃	263.337

下游产品

中文名称	英文名称	CAS号	化学式	分子量
(3AR,4R,6AS)-4-[[[(叔丁酯)二甲基硅烷基]氧基]甲基]四氢-2,2-二甲基-4H-1,3-二氧杂环戊烯并[4,5-C]吡咯	5-O-tert-butyldimethylsilyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol	153172-31-7	C₁₄H₂₉NO₃Si	287.475
——	1-amino-1,4-anhydro-N-tert-butoxycarbonyl-5-O-tertbutyldimethylsilyl-1-deoxy-2,3-O-isopropylidene-D-ribitol	178456-81-0	C₁₉H₃₇NO₅Si	387.592
1H-咪唑并[1,2-b]吡唑-2-醇,7-氨基-6-甲基-	7-O-tert-butyldimethylsilyl-2,3,6-trideoxy-3,6-imino-4,5-O-isopropylidene-D-allo-heptononitrile	222631-08-5	C₁₆H₃₀N₂O₃Si	326.511
——	4H-1,3-Dioxolo[4,5-c]pyrrole, 5-chloro-4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]tetrahydro-2,2-dimethyl-, (3aR,4R,6aS)-	153172-32-8	C₁₄H₂₈ClNO₃Si	321.92
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
——	(3aS,4S,6R,6aR)-tert-butyl 4-(2-(tert-butoxy)-2-oxoethyl)-6-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyldihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-5(4H)-carboxylate	——	C₂₅H₄₇NO₇Si	501.736
——	2-((3aS,6R,6aR)-6-(((tert-butyldimethylsilyl)oxy)methyl)-5-hydroxy-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrol-4-yl)acetonitrile	1610426-21-5	C₁₆H₃₀N₂O₄Si	342.511
——	tert-butyl (3aR,4R,6aR)-4-({[(tert-butyl)dimethylsilyl]oxy}methyl)-2,2-dimethyl-6-oxotetrahydro-5H-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate	178456-80-9	C₁₉H₃₅NO₆Si	401.576
——	(2S,3R,4S)-N-tert-butoxycarbonyl-2-hydroxymethyl-3,4-isopropylidenedioxypyrrolidine	154905-24-5	C₁₃H₂₃NO₅	273.329
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
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
——	(3aR,4R,6S,6aS)-4-(((tert-butyldimethylsilyl)oxy)methyl)-6-(2,6-dimethoxypyridin-3-yl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]	1610426-31-7	C₂₁H₃₆N₂O₅Si	424.613
——	(1S)-5-O-benzyl-N-tert-butoxycarbonyl-1-tert-butoxycarbonylmethyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol	577978-53-1	C₂₆H₃₉NO₇	477.598
——	tert-butyl (3aR,4R,6aS)-2,2-dimethyl-4-{[(methylsulfonyl)oxy]methyl}tetrahydro-5H-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate	1338787-17-9	C₁₄H₂₅NO₇S	351.421
——	5-O-tert-butyldimethylsilyl-1,N-dehydro-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol	153172-33-9	C₁₄H₂₇NO₃Si	285.459
——	(3aS,4S,6R,6aR)-tert-butyl 4-(2-amino-6-oxo-1,6-dihydropyrimidin-5-yl)-6-(hydroxymethyl)-2,2-dimethyldihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-5(4H)-carboxylate	1610426-14-6	C₁₇H₂₆N₄O₆	382.417
——	(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	C₂₆H₄₅N₃O₇Si	539.745
——	(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
——	(3aS,4S,6R,6aR)-tert-butyl 4-(2-amino-6-oxo-1,6-dihydropyrimidin-5-yl)-6-((benzyloxy)methyl)-2,2-dimethyldihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-5(4H)-carboxylate	1610426-19-1	C₂₄H₃₂N₄O₆	472.541
——	5-O-tert-butyldimethylsilyl-1,N-dehydro-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol N-oxide	607389-17-3	C₁₄H₂₇NO₄Si	301.458

反应信息

作为反应物：

描述：

(3AR,4R,6AS)-5-苄基-4-(((叔丁基二甲基硅烷基)氧基)甲基)-2,2-二甲基四在 selenium(IV) oxide 、正丁基锂、 palladium 10% on activated carbon 、 palladium on activated charcoal 、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、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 47.5h，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
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、 4-二甲氨基吡啶、 sodium tetrahydroborate 、 potassium hydroxide 作用下，以四氢呋喃、甲醇、水、 N,N-二甲基甲酰胺为溶剂，反应 98.0h，生成 (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

参考文献：

名称：

[EN] COMPOSITIONS AND METHODS FOR INHIBITING VIRAL POLYMERASE
[FR] COMPOSITIONS ET PROCÉDÉS D'INHIBITION D'UNE POLYMÉRASE VIRALE

摘要：

本文描述的是Formula (I)的化合物。Formula (I)的化合物在抑制病毒RNA聚合酶活性和病毒复制的方法中很有用。还提供了包含Formula (I)化合物的药物组合物，以及使用Formula (I)化合物治疗病毒感染的方法。

公开号：

WO2013158746A1

点击查看最新优质反应信息

文献信息

[EN] COMPOSITIONS AND METHODS FOR INHIBITING VIRAL POLYMERASE<br/>[FR] COMPOSITIONS ET PROCÉDÉS D'INHIBITION D'UNE POLYMÉRASE VIRALE

申请人：BIOCRYST PHARM INC

公开号：WO2013158746A1

公开（公告）日：2013-10-24

Provided are compounds of Formula (I) as described herein. Compounds of Formula (I) are useful in methods of inhibiting viral RNA polymerase activity and viral replication. Also provided are pharmaceutical compositions comprising compounds of Formula (I), as well as methods of treating viral infections using compounds of Formula (I).

本文描述的是Formula (I)的化合物。Formula (I)的化合物在抑制病毒RNA聚合酶活性和病毒复制的方法中很有用。还提供了包含Formula (I)化合物的药物组合物，以及使用Formula (I)化合物治疗病毒感染的方法。
A new class of C-nucleoside analogues. 1-(S)-aryl-1,4-dideoxy-1,4-imino-D-ribitols, transition state analogue inhibitors of nucleoside hydrolase

作者：Benjamin A. Horenstein、Roger F. Zabinski、Vern L. Schramm

DOI：10.1016/s0040-4039(00)79290-2

日期：1993.11

The first members of a new class of N-glycohydrolase transition state analogue inhibitors, 1,4-dideoxy-1,4-imino-1-(S)-phenyl-D-ribitol, 1, and 1,4-dideoxy-1,4-imino-1-(S)-(4-imidazolyl)-D-ribitol, 2, have been synthesized. These compounds represent a new type of C-nucleoside analogue in which the endocyclic ribosyl ring oxygen has been replaced with nitrogen. The key synthetic step involves reaction

新型N-糖水解酶过渡态类似物抑制剂的第一批成员1,4-dideoxy-1,4-imino-1-（S）-phenyl-D-ribitol，1和1,4-dideoxy-1 ，4-亚氨基-1-（S） - （4-咪唑基）-D-核糖醇，2，已被合成。这些化合物代表了一种新型的C-核苷类似物，其中的环内核糖基环氧已被氮取代。关键的合成步骤涉及受保护的核糖嘧啶与金属化的芳基物质的反应。该化合物是催化核苷的CN糖苷键水解的酶的过渡态类似物，并具有具有氧碳鎓离子特征的过渡态。化合物1和2是锥虫Crisidia fasciculata中核苷水解酶解离常数为0.03和2.5μM的有效竞争性抑制剂。观察到的高效抑制作用证明了在糖基化酶过渡态类似物中同时包含电荷和糖苷配基模拟物的重要性，并将其与简单的类似物区分开。
Inhibition of LuxS by S-ribosylhomocysteine analogues containing a [4-aza]ribose ring

作者：Venkata L.A. Malladi、Adam J. Sobczak、Tiffany M. Meyer、Dehua Pei、Stanislaw F. Wnuk

DOI：10.1016/j.bmc.2011.07.043

日期：2011.9

LuxS (S-ribosylhomocysteinase) catalyzes the cleavage of the thioether linkage of S-ribosylhomocysteine (SRH) to produce homocysteine and 4,5-dihydroxy-2,3-pentanedione (DPD), the precursor to a small signaling molecule that mediates interspecies bacterial communication called autoinducer 2 (AI-2). Inhibitors of LuxS should interfere with bacterial interspecies communication and potentially provide a novel class of antibacterial agents. In this work, SRH analogues containing substitution of a nitrogen atom for the endocyclic oxygen as well as various deoxyriboses were synthesized and evaluated for LuxS inhibition. Two of the [4-aza] SRH analogues showed modest competitive inhibition (K-I similar to 40 mu M), while most of the others were inactive. One compound that contains a hemiaminal moiety exhibited time-dependent inhibition, consistent with enzyme-catalyzed ring opening and conversion into a more potent species (K-I* = 3.5 mu M). The structure-activity relationship of the designed inhibitors highlights the importance of both the homocysteine and ribose moieties for high-affinity binding to LuxS active site. (C) 2011 Elsevier Ltd. All rights reserved.
[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