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2'-O-(tert-butyldimethylsilyl)docetaxel | 342613-14-3

分子结构分类

有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质

中文名称

——

中文别名

——

英文名称

2'-O-(tert-butyldimethylsilyl)docetaxel

英文别名

2'-(tert-butyldimethylsilyl)docetaxel；2'-O-tert-butyldimethylsilyldocetaxel；2'-TBDMS-docetaxel；2'-TBS-docetaxel；[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-15-[(2R,3S)-2-[tert-butyl(dimethyl)silyl]oxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]oxy-1,9,12-trihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate

2'-O-(tert-butyldimethylsilyl)docetaxel化学式

CAS

342613-14-3

化学式

C₄₉H₆₇NO₁₄Si

mdl

——

分子量

922.155

InChiKey

PXFKJUCGMIZCQC-BZYSWSIMSA-N

BEILSTEIN

——

EINECS

——

物化性质

沸点：

898.5±65.0 °C(Predicted)
密度：

1.27±0.1 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

6.29
重原子数：

65
可旋转键数：

16
环数：

6.0
sp3杂化的碳原子比例：

0.61
拓扑面积：

213
氢给体数：

4
氢受体数：

14

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
——	2'-TBS-7,10-TROC-docetaxel	152089-15-1	C₅₅H₆₉Cl₆NO₁₈Si	1272.95
多西他赛	Docetaxel	114977-28-5	C₄₃H₅₃NO₁₄	807.892

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	2’-TBS-cabazitaxel	1352816-81-9	C₅₁H₇₁NO₁₄Si	950.209
——	10-acetyl-2'-TBDMS-docetaxel	1144034-14-9	C₅₁H₆₉NO₁₅Si	964.192
——	2'-(tert-butyldimethylsilyl)-7,10-di(triethylsilyl)docetaxel	195141-96-9	C₆₁H₉₅NO₁₄Si₃	1150.68
多西他赛	Docetaxel	114977-28-5	C₄₃H₅₃NO₁₄	807.892
——	10-acetyldocetaxel	125354-16-7	C₄₅H₅₅NO₁₅	849.929
卡巴他赛	carbazitaxel	183133-96-2	C₄₅H₅₇NO₁₄	835.946
——	2'-O-(tert-butyldimethylsilyl)-3'-(de-tert-butoxycarbonyl)docetaxel	521087-17-2	C₄₄H₅₉NO₁₂Si	822.037
——	2'-O-tert-butyldimethylsilyl-7-O-triethylsilyldocetaxel	220985-01-3	C₅₁H₆₉NO₁₅Si	964.192
——	2'-(tert-butyldimethylsilyl)-2-debenzoyl-7,10-di(triethylsilyl)docetaxel	845639-07-8	C₅₄H₉₁NO₁₃Si₃	1046.57
——	2'-O-(tert-butyldimethylsilyl)-3'-(de-tert-butoxycarbonyl)-7,10-bis(triethylsilyl)docetaxel	521087-18-3	C₅₆H₈₇NO₁₂Si₃	1050.56
——	[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-15-[(2R,3S)-3-(4-bromobutanoylamino)-2-[tert-butyl(dimethyl)silyl]oxy-3-phenylpropanoyl]oxy-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9,12-bis(triethylsilyloxy)-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] 4-bromobutanoate	521087-15-0	C₅₇H₉₃Br₂NO₁₃Si₃	1244.43
——	[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-15-[(2R,3S)-3-(8-bromooctanoylamino)-2-[tert-butyl(dimethyl)silyl]oxy-3-phenylpropanoyl]oxy-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9,12-bis(triethylsilyloxy)-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] 6-bromohexanoate	521087-29-6	C₆₃H₁₀₅Br₂NO₁₃Si₃	1328.59
——	[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-15-[(2R,3S)-3-(8-bromooctanoylamino)-2-[tert-butyl(dimethyl)silyl]oxy-3-phenylpropanoyl]oxy-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9,12-bis(triethylsilyloxy)-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] 8-bromooctanoate	521087-30-9	C₆₅H₁₀₉Br₂NO₁₃Si₃	1356.64
——	[(2R,4S,5S,7R,10S,11R,12S,32S,33R,36S,38S)-33-[tert-butyl(dimethyl)silyl]oxy-38-hydroxy-4,39,39,40-tetramethyl-3,14,30,34-tetraoxo-32-phenyl-2,5-bis(triethylsilyloxy)-8,13,35-trioxa-22-thia-31-azapentacyclo[34.3.1.04,11.07,10.012,38]tetracont-1(40)-en-10-yl] acetate	521087-37-6	C₆₅H₁₀₉NO₁₃SSi₃	1228.9
——	[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-15-[(2R,3S)-3-(5-bromopentanoylamino)-2-[tert-butyl(dimethyl)silyl]oxy-3-phenylpropanoyl]oxy-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9,12-bis(triethylsilyloxy)-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] 5-bromopentanoate	521087-25-2	C₅₉H₉₇Br₂NO₁₃Si₃	1272.48
——	[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-15-[(2R,3S)-3-(6-bromohexanoylamino)-2-[tert-butyl(dimethyl)silyl]oxy-3-phenylpropanoyl]oxy-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9,12-bis(triethylsilyloxy)-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] 6-bromohexanoate	521087-27-4	C₆₁H₁₀₁Br₂NO₁₃Si₃	1300.54
——	[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-15-[(2R,3S)-3-(5-bromopentanoylamino)-2-[tert-butyl(dimethyl)silyl]oxy-3-phenylpropanoyl]oxy-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9,12-bis(triethylsilyloxy)-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] 4-bromobutanoate	521087-24-1	C₅₈H₉₅Br₂NO₁₃Si₃	1258.46
——	[(2R,4S,5S,7R,10S,11R,12S,28S,29R,32S,34S)-29-[tert-butyl(dimethyl)silyl]oxy-34-hydroxy-4,35,35,36-tetramethyl-3,14,26,30-tetraoxo-28-phenyl-2,5-bis(triethylsilyloxy)-8,13,31-trioxa-20-thia-27-azapentacyclo[30.3.1.04,11.07,10.012,34]hexatriacont-1(36)-en-10-yl] acetate	521087-34-3	C₆₁H₁₀₁NO₁₃SSi₃	1172.79
——	[(2R,4S,5S,7R,10S,11R,12S,30S,31R,34S,36S)-31-[tert-butyl(dimethyl)silyl]oxy-36-hydroxy-4,37,37,38-tetramethyl-3,14,28,32-tetraoxo-30-phenyl-2,5-bis(triethylsilyloxy)-8,13,33-trioxa-20-thia-29-azapentacyclo[32.3.1.04,11.07,10.012,36]octatriacont-1(38)-en-10-yl] acetate	521087-36-5	C₆₃H₁₀₅NO₁₃SSi₃	1200.85
——	[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-15-[(2R,3S)-3-(8-bromooctanoylamino)-2-[tert-butyl(dimethyl)silyl]oxy-3-phenylpropanoyl]oxy-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9,12-bis(triethylsilyloxy)-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] 5-bromopentanoate	521087-28-5	C₆₂H₁₀₃Br₂NO₁₃Si₃	1314.56
——	[(2R,4S,5S,7R,10S,11R,12S,24S,25R,28S,30S)-25-[tert-butyl(dimethyl)silyl]oxy-30-hydroxy-4,31,31,32-tetramethyl-3,14,22,26-tetraoxo-24-phenyl-2,5-bis(triethylsilyloxy)-8,13,27-trioxa-18-thia-23-azapentacyclo[26.3.1.04,11.07,10.012,30]dotriacont-1(32)-en-10-yl] acetate	521087-19-4	C₅₇H₉₃NO₁₃SSi₃	1116.69
——	[(2R,4S,5S,7R,10S,11R,12S,26S,27R,30S,32S)-27-[tert-butyl(dimethyl)silyl]oxy-32-hydroxy-4,33,33,34-tetramethyl-3,14,24,28-tetraoxo-26-phenyl-2,5-bis(triethylsilyloxy)-8,13,29-trioxa-19-thia-25-azapentacyclo[28.3.1.04,11.07,10.012,32]tetratriacont-1(34)-en-10-yl] acetate	521087-32-1	C₅₉H₉₇NO₁₃SSi₃	1144.74
——	[(2R,4S,5S,7R,10S,11R,12S,25S,26R,29S,31S)-26-[tert-butyl(dimethyl)silyl]oxy-31-hydroxy-4,32,32,33-tetramethyl-3,14,23,27-tetraoxo-25-phenyl-2,5-bis(triethylsilyloxy)-8,13,28-trioxa-18-thia-24-azapentacyclo[27.3.1.04,11.07,10.012,31]tritriacont-1(33)-en-10-yl] acetate	521087-31-0	C₅₈H₉₅NO₁₃SSi₃	1130.71
——	[(2R,4S,5S,7R,10S,11R,12S,29S,30R,33S,35S)-30-[tert-butyl(dimethyl)silyl]oxy-35-hydroxy-4,36,36,37-tetramethyl-3,14,27,31-tetraoxo-29-phenyl-2,5-bis(triethylsilyloxy)-8,13,32-trioxa-19-thia-28-azapentacyclo[31.3.1.04,11.07,10.012,35]heptatriacont-1(37)-en-10-yl] acetate	521087-35-4	C₆₂H₁₀₃NO₁₃SSi₃	1186.82
10-去乙酰基-N-去苯甲酰基紫杉醇	3'-aminodocetaxel	133524-69-3	C₃₈H₄₅NO₁₂	707.775
——	2-debenzoyl-2'-O-(tert-butyldimethylsilyl)-3'-(de-tert-butoxycarbonyl)-7,10-bis(triethylsilyl)docetaxel	521087-16-1	C₄₉H₈₃NO₁₁Si₃	946.455

反应信息

作为反应物：

描述：

2'-O-(tert-butyldimethylsilyl)docetaxel 在吡啶、咪唑、氢氟酸作用下，以四氢呋喃、 N,N-二甲基甲酰胺为溶剂，反应 2.5h，生成多西他赛

参考文献：

名称：

Radiosynthesis of[11C]docetaxel

摘要：

多西他赛（泰索帝®）是一种公认的用于治疗乳腺癌和非小细胞肺癌的化疗药物。一种潜在的预测反应的方法是利用正电子发射断层扫描（PET）测量肿瘤对[11C]多西他赛的摄取。遗憾的是，将11C同位素引入多西他赛的2-苯甲酰基部分的合成方法未能成功。然而，通过第二种合成方法，将11C同位素引入BOC部分，成功实现了[11C]多西他赛（6b，方案1）的放射合成。该方法始于[11C]叔丁醇与1,2,2,2-四氯乙基氯甲酸酯反应，生成[11C]叔丁基-1,2,2,2-四氯乙基碳酸酯，总体产率良好（62±9%）。在最后一步中，多西他赛的游离胺的[11C]叔丁氧羰酰化反应得到了[11C]多西他赛6b，经衰减校正的产率为令人满意的10±1%（来自[11C]CO2）。版权所有 © 2004 John Wiley & Sons, Ltd.

DOI：

10.1002/jlcr.861
作为产物：

描述：

2'-TBS-7,10-TROC-docetaxel 在溶剂黄146 、锌作用下，反应 5.0h，以81%的产率得到2'-O-(tert-butyldimethylsilyl)docetaxel

参考文献：

名称：

CABAZITAXEL, RELATED COMPOUNDS AND METHODS OF SYNTHESIS

摘要：

这项发明提供了新的卡巴吡嗪异丝氨酸酯中间体和新的合成方法，以及利用这些新的卡巴吡嗪异丝氨酸中间体制备抗肿瘤药物卡巴吡嗪、多西紫杉醇和紫杉醇的制备方法。

公开号：

US20140371474A1

点击查看最新优质反应信息

文献信息

Synthesis of Novel 2-O,3′-N-Linked Macrocyclic Taxoids with Variable Ring Size

作者：Olivier Querolle、Joëlle Dubois、Sylviane Thoret、Christophe Dupont、Françoise Guéritte、Daniel Guénard

DOI：10.1002/ejoc.200390092

日期：2003.2

A series of macrocyclic taxoids was prepared by connecting the 2-OH and 3′-NH moieties with aliphatic chains to mimic the docetaxel solid-state conformation. The synthesis was achieved by acylation of both positions with various bromoalkanoic acids, and ring closure was carried out with sodium sulfide. Nine 19- to 27-membered macrocyclic taxoids were obtained and evaluated as inhibitors of microtubule

通过将 2-OH 和 3'-NH 部分与脂肪链连接以模拟多西紫杉醇的固态构象，制备了一系列大环紫杉醇。合成是通过用各种溴链烷酸酰化两个位置来实现的，并用硫化钠进行闭环。获得了九个 19 至 27 元大环紫杉醇，并评估了它们作为微管分解抑制剂及其细胞毒性。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
Ferrocenyl Paclitaxel and Docetaxel Derivatives: Impact of an Organometallic Moiety on the Mode of Action of Taxanes

作者：Anna Wieczorek、Andrzej Błauż、Aleksandra Żal、Homayon John Arabshahi、Jóhannes Reynisson、Christian G. Hartinger、Błażej Rychlik、Damian Plażuk

DOI：10.1002/chem.201601809

日期：2016.8.1

A series of ferrocenyl analogues and derivatives of paclitaxel and docetaxel were synthesised and assayed for their antiproliferative/cytotoxic effects, impact on the cell cycle distribution and ability to induce tubulin polymerisation. The replacement of the 3′‐N‐benzoyl group of paclitaxel with a ferrocenoyl moiety, in particular, led to formation of an analogue that was at least one order of magnitude

合成了一系列紫杉醇和紫杉醇的二茂铁基类似物和衍生物，并对其抗增殖/细胞毒性作用，对细胞周期分布的影响以及诱导微管蛋白聚合的能力进行了测定。紫杉醇的3'- N-苯甲酰基被二茂铁酰基取代，特别是导致其抗增殖活性比母体化合物高至少一个数量级的类似物形成（IC 50值的0.11与1.11μ米），但仍保留了经典的紫杉烷的作用方式，即微管稳定导致有丝分裂停滞。分子对接研究表明，紫杉醇骨架中引入的二茂铁酰基的微管蛋白结构中有一个意外的结合口袋。
[EN] CABAZITAXEL, RELATED COMPOUNDS AND METHODS OF SYNTHESIS<br/>[FR] CABAZITAXEL, COMPOSÉS APPARENTÉS ET PROCÉDÉS DE SYNTHÈSE

申请人：BARTON MATTHEW THOMAS

公开号：WO2013057260A1

公开（公告）日：2013-04-25

The invention provides new cabazitaxel isoserine ester intermediates and new synthetic methods, and a preparation method for the anti-tumour drugs cabazitaxel, docetaxel and paclitaxel from the new cabazitaxel isoserine intermediates.

这项发明提供了新的卡巴嗪异丝氨酸酯中间体和新的合成方法，以及从新的卡巴嗪异丝氨酸中间体制备抗肿瘤药物卡巴嗪、多西紫杉醇和紫杉醇的方法。
Nevarez, Danielle M.; Mengistu, Yemane A.; Nawarathne, Irosha N., Journal of the American Chemical Society, 2009, vol. 131, p. 5994 - 6002

作者：Nevarez, Danielle M.、Mengistu, Yemane A.、Nawarathne, Irosha N.、Walker, Kevin D.

DOI：——

日期：——
Synthesis of Docetaxel and Butitaxel Analogues through Kinetic Resolution of Racemic β-Lactams with 7-<i>O</i>-Triethylsilylbaccatin III

作者：Haibo Ge、Jared T. Spletstoser、Yan Yang、Margaret Kayser、Gunda I. Georg

DOI：10.1021/jo061339s

日期：2007.2.1

The kinetic resolution of racemic cis-4-phenyl- and cis-4-tert-butyl-3-hydroxy-beta-lactam derivatives with 7-O-triethylsilylbaccatin III yielded paclitaxel and butitaxel analogues with high diastereoselectivity. The results demonstrated that the tert-butyldimethylsilyl protecting group at the C3-hydroxy group of the beta-lactams provided optimum kinetic resolution in comparison with the sterically less demanding triethylsilyl group and the larger triisopropylsilyl group. In addition, it was found that the C4 beta-lactam substituents also influenced diastereoselectivity. The C4 tert-butyl-beta-lactams provided better diastereoselectivity than the corresponding C4 phenyl beta-lactams.