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de-A,B-8β,22-di-[(tert-butyldimethyl)silyloxy]-23,24-dinorcholane | 189102-76-9

分子结构分类

有机化合物 - 有机金属化合物 - 有机类金属化合物

中文名称

——

中文别名

——

英文名称

de-A,B-8β,22-di-[(tert-butyldimethyl)silyloxy]-23,24-dinorcholane

英文别名

——

de-A,B-8β,22-di-[(tert-butyldimethyl)silyloxy]-23,24-dinorcholane化学式

CAS

189102-76-9

化学式

C₂₅H₅₂O₂Si₂

mdl

——

分子量

440.858

InChiKey

GSXSZWXWEBVUKE-SHNSKLSNSA-N

BEILSTEIN

——

EINECS

——

物化性质

沸点：

425.0±18.0 °C(Predicted)
密度：

0.90±0.1 g/cm3(Predicted)
溶解度：

溶于氯仿

计算性质

辛醇/水分配系数(LogP)：

8.25
重原子数：

29.0
可旋转键数：

6.0
环数：

2.0
sp3杂化的碳原子比例：

1.0
拓扑面积：

18.46
氢给体数：

0.0
氢受体数：

2.0

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
(1R,3AR,4S,7AR)-1-[(2S)-1-羟基丙-2-基]-7A-甲基-1,2,3,3A,4,5,6,7-八氢茚-4-醇	(8S,20S)-de-A,B-20-(hydroxymethyl)pregnan-8-ol	64190-52-9	C₁₃H₂₄O₂	212.332

下游产品

中文名称	英文名称	CAS号	化学式	分子量
骨化醇杂质DCP	(20R)-de-A,B-8β-[(tert-butyldimethylsilyl)oxy]-20-(hydroxymethyl)pregnane	171011-48-6	C₁₉H₃₈O₂Si	326.595
(BETAS,1R,3AR,4S,7AR)-4-[[(叔丁基)二甲基硅烷基]氧基]八氢-BETA,7A-二甲基-1H-茚-1-乙醇	(S)-2-((1R,3aR,4S,7aR)-4-(tert-butyldimethylsilyloxy)-7a-methyloctahydro-1H-inden-1-yl)propan-1-ol	100928-03-8	C₁₉H₃₈O₂Si	326.595
——	(2S)-2-((1R,3aR,4S,7aR)-4-((tert-butyldimethylsilyl)oxy)-7a-methyloctahydro-1H-inden-1-yl)hex-5-yn-3-ol	1361587-87-2	C₂₂H₄₀O₂Si	364.644
——	(S)-2-[(1R,3aR,4S,7aR)-octahydro-4-[(1,1-dimethylethyl)dimethylsilyloxy]-7a-methyl-1H-inden-1-yl]propanal	104651-47-0	C₁₉H₃₆O₂Si	324.579
艾地骨化醇起始原料杂质1	de-A,B-8β-<(tert-butyldimethylsilyl)oxy>-23,24-dinor-23-iodocholane	100928-05-0	C₁₉H₃₇IOSi	436.492
——	(S)-5-((1R,3aR,4S,7aR)-4-(tert-butyldimethylsilyloxy)-7a-methyloctahydro-1H-inden-1-yl)-1-ethoxyhex-1-ene	1235544-62-3	C₂₄H₄₆O₂Si	394.714
——	(S)-5-((1R,3aR,4S,7aR)-4-(tert-butyldimethylsilyloxy)-7a-methyloctahydro-1H-inden-1-yl)-1-ethoxyhex-1-ene	957214-08-3	C₂₄H₄₆O₂Si	394.714
——	[(1R,3aR,4S,7aR)-7a-methyl-1-[(2R)-1-(4-methyl-4-trimethylsilyloxypentoxy)propan-2-yl]-1,2,3,3a,4,5,6,7-octahydroinden-4-yl]oxy-tert-butyl-dimethylsilane	1026545-21-0	C₂₈H₅₈O₃Si₂	498.938
艾地骨化醇起始物料杂质2	[1R-(1β,3aα,7aβ)]-[1S-(4β)]-(1,1-dimethylethyl)dimethyl{[octahydro-7a-methyl-1-(1-methylethenyl)-1H-inden-4-yl]oxy}silane	215257-72-0	C₁₉H₃₆OSi	308.58
——	(4E,6E,8R)-8-[(1R,3aR,4S,7aR)-4-[tert-butyl(dimethyl)silyl]oxy-7a-methyl-1,2,3,3a,4,5,6,7-octahydroinden-1-yl]-3-ethylnona-4,6-dien-3-ol	189102-32-7	C₂₇H₅₀O₂Si	434.778
——	ethyl (2E,4E,6R)-6-[(1R,3aR,4S,7aR)-4-[tert-butyl(dimethyl)silyl]oxy-7a-methyl-1,2,3,3a,4,5,6,7-octahydroinden-1-yl]hepta-2,4-dienoate	189102-31-6	C₂₅H₄₄O₃Si	420.708
——	8β-[(tert-butyldimethylsilyl)oxy]de-A,B-androstan-17β-one	140659-26-3	C₁₆H₃₀O₂Si	282.498
——	(S)-2-((1R,3aR,4S,7aR)-4-((tert-butyldimethylsilyl)oxy)-7a-methyloctahydro-1H-inden-1-yl)propyl isonicotinate	1454816-56-8	C₂₅H₄₁NO₃Si	431.691
——	(S)-2-((1R,3aR,4S,7aR)-4-((tert-butyldimethylsilyl)oxy)-7a-methyloctahydro-1H-inden-1-yl)propyl 4-chlorobenzoate	1454816-54-6	C₂₆H₄₁ClO₃Si	465.148
——	(S)-2-((1R,3aR,4S,7aR)-4-((tert-butyldimethylsilyl)oxy)-7a-methyloctahydro-1H-inden-1-yl)propyl 2-naphthoate	1454816-59-1	C₃₀H₄₄O₃Si	480.763
——	(S)-2-((1R,3aR,4S,7aR)-4-((tert-butyldimethylsilyl)oxy)-7a-methyloctahydro-1H-inden-1-yl)propyl furan-2-carboxylate	1454816-57-9	C₂₄H₄₀O₄Si	420.665
——	(S)-2-((1R,3aR,4S,7aR)-4-((tert-butyldimethylsilyl)oxy)-7a-methyloctahydro-1H-inden-1-yl)propyl 4-methoxybenzoate	1454816-53-5	C₂₇H₄₄O₄Si	460.729
——	(S)-2-((1R,3aR,4S,7aR)-4-((tert-butyldimethylsilyl)oxy)-7a-methyloctahydro-1H-inden-1-yl)propyl nicotinate	1454816-55-7	C₂₅H₄₁NO₃Si	431.691
——	(20R)-de-A,B-8β-[(tert-butyldimethylsilyl)oxy]-20-[(p-tolylsulfonyl)oxymethyl]pregnane	183506-75-4	C₂₆H₄₄O₄SSi	480.784
——	(S)-2-((1R,3aR,4S,7aR)-4-((tert-butyldimethylsilyl)oxy)-7a-methyloctahydro-1H-inden-1-yl)propyl 1-naphthoate	1454816-58-0	C₃₀H₄₄O₃Si	480.763
——	(S)-2-((1R,3aR,4S,7aR)-4-((tert-butyldimethylsilyl)oxy)-7a-methyloctahydro-1H-inden-1-yl)propyl 3-methoxybenzoate	1454816-52-4	C₂₇H₄₄O₄Si	460.729
——	tert-butyl(((1R,3aR,4S,7aR)-1-((S)-1-(furan-2-yl)ethyl)-7a-methyloctahydro-1H-inden-4-yl)oxy)dimethylsilane	1361587-89-4	C₂₂H₃₈O₂Si	362.628
——	(S)-2-((1R,3aR,4S,7aR)-4-((tert-butyldimethylsilyl)oxy)-7a-methyloctahydro-1H-inden-1-yl)propyl 2-methoxybenzoate	1454816-51-3	C₂₇H₄₄O₄Si	460.729

反应信息

作为反应物：

描述：

de-A,B-8β,22-di-[(tert-butyldimethyl)silyloxy]-23,24-dinorcholane 在 4-二甲氨基吡啶、四丁基氟化铵、 N,N'-二环己基碳二亚胺作用下，以四氢呋喃、二氯甲烷为溶剂，生成 (S)-2-((1R,3aR,4S,7aR)-4-((tert-butyldimethylsilyl)oxy)-7a-methyloctahydro-1H-inden-1-yl)propyl 2-methoxybenzoate

参考文献：

名称：

Analogues of the Inhoffen–Lythgoe diol with anti-proliferative activity

摘要：

The anti-proliferative activity of a series of ester-and amide-linked Inhoffen-Lythgoe side chain analogues is reported. Whereas the Inhoffen-Lythgoe diol was inactive in these studies, a number of aromatic and aliphatic ester-linked side chains demonstrated modest in vitro growth inhibition in two human cancepar cell lines, U87MG (glioblastoma) and HT-29 (colorectal adenocarcinoma). Structureactivity relationship (SAR) studies demonstrated the most active aromatic (13) and aliphatic (25 and 29) substituted analogues were approximately equipotent in U87MG and HT-29 cells. Further evaluation of 13, 25, and 29 indicated these analogues do not activate canonical vitamin D signaling nor antagonize Hedgehog (Hh) signaling. Thus, the cellular mechanism(s) that govern the anti-proliferative activity for this class of truncated vitamin D-based structures appears to be different from classical mechanisms previously identified for these scaffolds. (C) 2013 Elsevier Ltd. All rights reserved.

DOI：

10.1016/j.bmcl.2013.07.054
作为产物：

描述：

维生素D2 在 2,6-二甲基吡啶、 sodium tetrahydroborate 、氧气、碳酸氢钠、臭氧作用下，以 N,N-二甲基甲酰胺为溶剂，反应 5.0h，生成 de-A,B-8β,22-di-[(tert-butyldimethyl)silyloxy]-23,24-dinorcholane

参考文献：

名称：

激素1alpha，25-Dihydroxyvitamin D（3）的抗增殖杂交类似物：设计，合成和初步生物学评估。

摘要：

10-12 kbar压力与Lewis酸性二氯化锌的结合促进了以新方法制备的3-溴-2-吡喃酮与未活化的末端烯烃4-（叔丁基二甲基甲硅烷氧基）-1之间的高度区域选择性和立体选择性Diels-Alder环加成反应-丁烯。A环烯丙基氧化膦20的共轭碱将化学特异性地添加到某些C-8，C-24-二酮的C-8酮基上，从而直接形成1alpha，25-dihydroxyvitamin D（3）的具有抗新陈代谢作用的24-oxo类似物。（骨化三醇）。这些新的杂合类似物中的几种在体外抑制钙质细胞生长的作用与钙三醇一样，即使在生理上相关的10-100纳摩尔浓度下也是如此。

DOI：

10.1021/jo970049w

点击查看最新优质反应信息

文献信息

Modified Julia olefination and α aminoxylation reactions mediated convergent synthesis of 1α, 24 (R)-dihydroxyvitamin D3 (tacalcitol)

作者：Andrea Martínez、Hugo Santalla、Fátima Garrido、Generosa Gómez、Yagamare Fall

DOI：10.1016/j.tetlet.2017.07.103

日期：2017.9

A convergent synthesis of tacalcitol has been achieved starting from inexpensive and commercially available isovaleraldehyde and easily available Inhoffen-Lythgoe diol. Key steps include a proline catalyzed α aminoxylation and a Julia-Kocienski olefination.

从廉价的和可商购的异戊醛和容易获得的Inhoffen-Lythgoe二醇开始，已经实现了塔骨化醇的收敛合成。关键步骤包括脯氨酸催化的α氨氧基化和Julia-Kocienski烯烃化。
1.alpha.,25-Dihydroxyvitamin D3 Analogs Featuring Aromatic and Heteroaromatic Rings: Design, Synthesis, and Preliminary Biological Testing

作者：Gary H. Posner、Zhengong Li、M. Christina White、Victoria Vinader、Kazuhiro Takeuchi、Sandra E. Guggino、Patrick Dolan、Thomas W. Kensler

DOI：10.1021/jm00022a019

日期：1995.10

activities in murine keratinocytes at micromolar concentration. No biological advantage was observed in this keratinocyte assay for the doubly modified hybrid analogs 20a-c over the singly modified parent (+)-2b. Analog (+)-2b, but surprisingly not the corresponding analog 20b differing from (+)-2b only in the side chain, showed considerable activity in nongenomic opening of calcium channels in rat osteosarcoma

设计了芳香族化合物2a-c，1 alpha 25-二羟基维生素（骨化三醇1）的类似物以及杂芳香族化合物4a-c和5a-c 19-nor-1 alpha 25-dihydroxyvitamin D3（3）的类似物。模拟其生物有效母体化合物的拓扑结构，同时避免维生素原D平衡。通过将对映体形成的有机锂亲核试剂羰基加成到对映体纯的C，D-上，可以实现类似物（+）-2b，（+）-2c，（-）-4b和（-）-5b的聚合合成。环酮（+）-17，天然骨化三醇（1）的特征。同样，制备杂合类似物20a-c，以确定掺入已知的增强侧链是否会导致生物活性增加。初步的体外生物学测试表明，芳香族类似物（+）-2b，（+）-2c，和20a-c以及杂芳族类似物（-）-4b和（-）-5b对小牛胸腺维生素D受体的亲和力很低，但在鼠角质形成细胞中以微摩尔浓度存在明显的抗增殖活性。在该角质形成细胞测定中，没有观察到与单修饰的亲本（
Design, Synthesis, Evaluation, and Structure of Vitamin D Analogues with Furan Side Chains

作者：Ramón Fraga、Flavia Zacconi、Fredy Sussman、Paloma Ordóñez-Morán、Alberto Muñoz、Tiphaine Huet、Ferdinand Molnár、Dino Moras、Natacha Rochel、Miguel Maestro、Antonio Mouriño

DOI：10.1002/chem.201102695

日期：2012.1.9

tetrahydrofuran ring at the side chain that optimize the aliphatic side‐chain conformation through an entropy benefit. Following a similar strategy, four novel vitamin D analogues with aromatic furan side chains (3 a, 3 b, 4 a, 4 b) have now been developed. The triene system has been constructed by an efficient stereoselective intramolecular cyclization of an enol triflate (A‐ring precursor) followed

基于与1α，25-二羟基维生素D 3（1,25 D ）结合的人类维生素D受体（hVDR）的晶体结构和超激动剂配体，我们先前设计了在侧链具有四氢呋喃环的新型超激动剂配体，从而优化了通过熵的好处实现脂肪族侧链构象。遵循类似的策略，四个具有芳香族呋喃侧链的新型维生素D类似物（3a，3b，4a，4b）现已开发。三烯体系的构建是通过对三氟甲磺酸酯（A环前体）进行高效的立体选择性分子内环化，然后将所得中间体与烯基硼酸酯（CD侧链，上部片段）进行铃木-宫浦偶联。呋喃侧链已通过金化学方法构建。这些类似物表现出显着的前分化作用和反式激活潜能。3 a的晶体结构与hVDR的配体结合结构域形成复合物，表明侧链呋喃环具有两个构象。
Synthesis of a<i>trans</i>-Hydrindanone, Precursor for the Preparation of Vitamin D Analogues

作者：Zoila Gándara、Marcos L. Rivadulla、Manuel Pérez、Generosa Gómez、Yagamare Fall

DOI：10.1002/ejoc.201300528

日期：2013.9

developed a very efficient and practical method for the large-scale synthesis of a trans-hydrindan derivative related to vitamin D, based on the Criegee rearrangement. This ketone is a valuable synthon for the preparation of Gemini-type vitamin D analogues or other calcitriol analogues modified at C-20, C-21 or the D-ring. Our methodology is superior to those previously reported when considering efficiency

基于 Criegee 重排，我们开发了一种非常有效且实用的方法，用于大规模合成与维生素 D 相关的反式三氢呋喃衍生物。这种酮是用于制备双子型维生素 D 类似物或其他在 C-20、C-21 或 D 环上修饰的骨化三醇类似物的有价值的合成子。在考虑效率和便利时，我们的方法优于先前报告的方法。
[EN] HYBRID MOLECULES HAVING MIXED VITAMIN D RECEPTOR AGONISM AND HISTONE DEACETYLASE INHIBITORY PROPERTIES<br/>[FR] MOLÉCULES HYBRIDES ASSOCIANT AUX PROPRIÉTÉS D'AGONISME DU RÉCEPTEUR DE LA VITAMINE D, DES PROPRIÉTÉS D'INHIBITION DE L'HISTONE DÉSACÉTYLASE

申请人：UNIV MCGILL

公开号：WO2009117831A9

公开（公告）日：2009-12-30