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(3Z,5S,6S,7S,8R,9R,11Z,13S,14R,15S)-14-(t-butyldimethylsilyloxy)-6,16-bis(p-methoxybenzyloxy)-9-(hydroxymethyl)-5,7,11,13,15-pentamethylhexadeca-1,3,11-trien-8-ol | 373645-65-9

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

(3Z,5S,6S,7S,8R,9R,11Z,13S,14R,15S)-14-(t-butyldimethylsilyloxy)-6,16-bis(p-methoxybenzyloxy)-9-(hydroxymethyl)-5,7,11,13,15-pentamethylhexadeca-1,3,11-trien-8-ol

英文别名

(3Z,11Z)-14-(t-butyldimethylsilyloxy)-6,16-bis-(p-methoxybenzyloxy)-9-(hydroxymethyl)-5,7,11,13,15-pentamethyl-hexadeca-1,3,11-trien-8-ol；(2R,3R,4S,5S,6S,7Z)-2-[(Z,4S,5R,6S)-5-[tert-butyl(dimethyl)silyl]oxy-7-[(4-methoxyphenyl)methoxy]-2,4,6-trimethylhept-2-enyl]-5-[(4-methoxyphenyl)methoxy]-4,6-dimethyldeca-7,9-diene-1,3-diol

(3Z,5S,6S,7S,8R,9R,11Z,13S,14R,15S)-14-(t-butyldimethylsilyloxy)-6,16-bis(p-methoxybenzyloxy)-9-(hydroxymethyl)-5,7,11,13,15-pentamethylhexadeca-1,3,11-trien-8-ol化学式

CAS

373645-65-9

化学式

C₄₄H₇₀O₇Si

mdl

——

分子量

739.121

InChiKey

DHLCVWPLELYYRM-WCVPPTKSSA-N

BEILSTEIN

——

EINECS

——

物化性质

沸点：

748.5±60.0 °C(Predicted)
密度：

1.015±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

辛醇/水分配系数(LogP)：

9.79
重原子数：

52
可旋转键数：

24
环数：

2.0
sp3杂化的碳原子比例：

0.59
拓扑面积：

86.6
氢给体数：

2
氢受体数：

7

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
——	(Z)-(6S,7R,8S)-7-(tert-butyldimethylsilanyloxy)-9-(4-methoxybenzyloxy)-4,6,8-trimethylnon-4-enoic acid methyl ester	261968-16-5	C₂₇H₄₆O₅Si	478.745
——	(2,6-dimethylphenyl) (2S,3S,4S,5S,6S,7Z)-2-[(2Z,4S,5R,6S)-5-(t-butyldimethylsilyloxy)-7-(p-methoxybenzyloxy)-2,4,6-trimethyl-hept-2-enyl]-3-hydroxy-5-(p-methoxybenzyloxy)-4,6-dimethyldeca-7,9-dienoate	261968-21-2	C₅₂H₇₆O₈Si	857.256
——	(4-methoxy-2,6-dimethylphenyl) (2S,3S,4S,5S,6S,7Z)-2-[(2Z,4S,5R,6S)-5-(t-butyldimethylsilyloxy)-7-(p-methoxybenzyloxy)-2,4,6-trimethylhept-2-enyl]-3-hydroxy-5-(p-methoxybenzyloxy)-4,6-dimethyldeca-7,9-dienoate	827603-09-8	C₅₃H₇₈O₉Si	887.282
——	methyl (2Z,4S,5R,6S)-5-(t-butyldimethylsilyloxy)-7-(p-methoxybenzyloxy)-2,4,6-trimethylhept-2-enoate	496035-40-6	C₂₅H₄₂O₅Si	450.691
——	(+)-tert-butyl-[(Z)-(2S,3S,4S)-3-(4-methoxybenzyloxy)-2,4-dimethylocta-5,7-dienyloxy]dimethylsilane	184291-96-1	C₂₄H₄₀O₃Si	404.665
——	(Z)-(6S,7R,8S)-7-(tert-butyldimethylsilanyloxy)-9-(4-methoxybenzyloxy)-4,6,8-trimethylnon-4-enoic acid 2,6-dimethylphenyl ester	261968-07-4	C₃₄H₅₂O₅Si	568.869
——	[2S,4S,5R,6S]-7-(t-butyldimethylsilyloxy)-5-(p-methoxybenzyloxy)-4,6-dimethylheptan-2,3-diol	261968-19-8	C₂₃H₄₂O₅Si	426.669
——	4-methoxy-2,6-dimethylphenyl (4Z,6S,7R,8S)-7-(t-butyldimethylsilyloxy)-9-(p-methoxybenzyloxy)-4,6,8-trimethylnon-4-enoate	496035-34-8	C₃₅H₅₄O₆Si	598.896
——	(+)-(2S,3S,4S)-5-(tert-butyldimethylsilanyloxy)-3-(4-methoxybenzyloxy)-2,4-dimethylpentan-1-ol	496035-39-3	C₂₁H₃₈O₄Si	382.616
——	(+)-tert-butyl-{(S)-2-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]propoxy}dimethylsilane	496035-38-2	C₂₁H₃₆O₄Si	380.6
——	(+)-(Z)-(2S,3S,4S)-3-(4-methoxybenzyloxy)-2,4-dimethylocta-5,7-dien-1-ol	184291-36-9	C₁₈H₂₆O₃	290.403
——	(-)-(2R,3R,4S)-5-(tert-butyldimethylsilanyloxy)-3-(4-methoxybenzyloxy)-2,4-dimethylpentanal	261968-20-1	C₂₁H₃₆O₄Si	380.6
——	[(3R,4R,5S,6S)-5-hydroxy-7-[(4-methoxyphenyl)methoxy]-2,4,6-trimethylhept-1-en-3-yl] propanoate	261968-13-2	C₂₁H₃₂O₅	364.482
——	1-(p-methoxybenzyloxy)-3,5-dihydroxy-2,4,6-trimethyl-6-heptene	373645-63-7	C₁₈H₂₈O₄	308.418
——	6-[1-(p-methoxybenzyloxy)-2-propyl]-2-(phenylseleno)methyl-4-isopropenyl-[1,3]-dioxane	261968-14-3	C₂₆H₃₄O₄Se	489.514

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	(3Z,5S,6S,7S,8R,9S,11Z,13S,14R,15S)-14-(t-butyldimethylsilyloxy)-6,16-bis-(p-methoxybenzyloxy)-5,7,9,11,13,15-hexamethyl-hexadeca-1,3,11-trien-8-ol	261968-22-3	C₄₄H₇₀O₆Si	723.122
——	1-[(5Z,13Z)-(2S,3R,4S,8S,9R,10R,11S,12S)-11-(4-methoxybenzoxy)-3,9-bis(tert-butyldimethylsilanyloxy)-2,4,6,8,10,12-hexamethylhexadeca-5,13,15-trienyloxymethyl]-4-methoxybenzene	256920-81-7	C₅₀H₈₄O₆Si₂	837.384
——	tert-butyl-[(Z,2S,3R,4S)-1-[(4-methoxyphenyl)methoxy]-7-[(2R,3R)-2-[(2R,3S,4S,5Z)-3-[(4-methoxyphenyl)methoxy]-4-methylocta-5,7-dien-2-yl]oxetan-3-yl]-2,4,6-trimethylhept-5-en-3-yl]oxy-dimethylsilane	373645-83-1	C₄₄H₆₈O₆Si	721.106
——	(3Z,5S,6S,7R,8S,9R,11Z,13S,14R,15S)-14-(t-butyldimethylsilyloxy)-6,16-bis(p-methoxybenzyloxy)-9-[(2,4,6-trimethylphenyl)sulfoxymethyl]-5,7,11,13,15-pentamethyl-hexadeca-1,3,11-trien-8-ol	373645-66-0	C₅₃H₈₀O₉SSi	921.364
——	Carbamic acid (6Z,11Z)-(1S,2R,3R,4R,8S,9S,10S)-3,9-bis-(tert-butyl-dimethyl-silanyloxy)-4-(tert-butyl-dimethyl-silanyloxymethyl)-2,6,8,10-tetramethyl-1-((Z)-(S)-1-methyl-penta-2,4-dienyl)-13-oxo-trideca-6,11-dienyl ester	646031-63-2	C₄₃H₈₃NO₆Si₃	794.392
——	carbamic acid (6Z,11Z)-(1S,2R,3R,4S,8S,9S,10S)-3,9-bis(tert-butyldimethylsilanyloxy)-13-hydroxy-2,4,6,8,10-pentamethyl-1-((Z)-(S)-1-methylpenta-2,4-dienyl)-trideca-6,11-dienyl ester	373645-74-0	C₃₇H₇₁NO₅Si₂	666.145
——	carbamic acid (6Z,11Z)-(1S,2R,3R,4S,8S,9S,10S)-3,9-bis(tert-butyldimethylsilanyloxy)-2,4,6,8,10-pentamethyl-1-((Z)-(S)-1-methylpenta-2,4-dienyl)-13-oxo-trideca-6,11-dienyl ester	261968-08-5	C₃₇H₆₉NO₅Si₂	664.13
——	(3Z,5S,6S,7S,8Z,11S,12R,13S,14S,15S,16Z)-6,12-bis(tert-butyldimethylsilyloxy)-14-carbamoyloxy-5,7,9,11,13,15-bexamethyl-nonadeca-3,8,16,18-tetraen-2-one	496035-33-7	C₃₈H₇₁NO₅Si₂	678.156
——	(2Z,4S,5S,6S,7Z,10S,11R,12R,13S,14S,15Z)-13-[(aminocarbonyl)oxy]-5,11-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4,6,8,10,12,14-hexamethyl-2,7,15,17-octadecatetraenoic acid methyl ester	373645-73-9	C₃₈H₇₁NO₆Si₂	694.156
——	Carbamic acid (Z)-(1S,2S)-1-((S)-1-{(2R,3R)-3-[(2Z,7Z)-(4S,5S,6S)-5-(tert-butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-9-oxo-nona-2,7-dienyl]-oxetan-2-yl}-ethyl)-2-methyl-hexa-3,5-dienyl ester	646031-68-7	C₃₁H₅₃NO₅Si	547.851
——	(3Z,11Z)-(5S,6S,7S,8R,9S,13S,14R,15S)-8,14-bis-(tertbutyldimethylsilanyloxy)-5,7,9,11,13,15-hexamethyl-6,16-bis-triethylsilanyloxyhexadeca-1,3,11-triene	261968-23-4	C₃₄H₆₈O₄Si₂	597.083
——	methyl (2R,3S,4R,7S,8Z,10S,11S,12S,13Z,16R,17R,18R,19S,20S,21Z)-3,11,17-tris[[tert-butyl(dimethyl)silyl]oxy]-16-[[tert-butyl(dimethyl)silyl]oxymethyl]-19-carbamoyloxy-7-hydroxy-2,4,10,12,14,18,20-heptamethyl-5-oxotetracosa-8,13,21,23-tetraenoate	646031-64-3	C₅₈H₁₁₃NO₁₀Si₄	1096.88
——	(2Z,7Z,15Z)-(4S,5S,6S,10S,11R,12R,13S,14S)-5,11-bis(tert-butyldimethylsilanyloxy)-13-hydroxy-4,6,8,10,12,14-hexamethyloctadeca-2,7,15,17-tetraenoic acid methyl ester	261968-24-5	C₃₇H₇₀O₅Si₂	651.131
——	(2R,13Z)-3,9-bis-(t-butyldimethylsilyloxy)-11-hydroxy-2,4,6,8,10,12-hexamethyl-hexadeca-5,13,15-trienal	373645-86-4	C₃₄H₆₆O₄Si₂	595.067
——	methyl (2R,3S,4R,7S,8Z,10S,11S,12S,13Z)-11-[tert-butyl(dimethyl)silyl]oxy-15-[(2R,3R)-2-[(2S,3S,4S,5Z)-3-carbamoyloxy-4-methylocta-5,7-dien-2-yl]oxetan-3-yl]-7-hydroxy-2,4,10,12,14-pentamethyl-5-oxo-3-triethylsilyloxypentadeca-8,13-dienoate	646031-70-1	C₄₆H₈₃NO₉Si₂	850.337

反应信息

作为反应物：

描述：

(3Z,5S,6S,7S,8R,9R,11Z,13S,14R,15S)-14-(t-butyldimethylsilyloxy)-6,16-bis(p-methoxybenzyloxy)-9-(hydroxymethyl)-5,7,11,13,15-pentamethylhexadeca-1,3,11-trien-8-ol 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 lithium aluminium tetrahydride 、 18-冠醚-6 、碘苯二乙酸、邻苯二甲酸二甲酯、二异丁基氢化铝、 potassium carbonate 、三乙胺、 2,3-二氯-5,6-二氰基-1,4-苯醌作用下，以四氢呋喃、甲醇、二氯甲烷、甲苯为溶剂，反应 77.5h，生成 carbamic acid (6Z,11Z)-(1S,2R,3R,4S,8S,9S,10S)-3,9-bis(tert-butyldimethylsilanyloxy)-2,4,6,8,10-pentamethyl-1-((Z)-(S)-1-methylpenta-2,4-dienyl)-13-oxo-trideca-6,11-dienyl ester

参考文献：

名称：

使用手性酮的硼介导的醛醇缩合反应合成抗微管剂（+）-Discodermolide。

摘要：

具有与紫杉醇相似的作用机理，标题化合物1是癌症化学疗法发展中特别有希望的候选者。这种基于立体控制的醛醇缩合反应的有效合成方法应有助于克服稀有海绵来源的稀缺天然物质1的供应。

DOI：

10.1002/(sici)1521-3773(20000117)39:2<377::aid-anie377>3.0.co;2-e
作为产物：

描述：

(2S,4R,5R,6S)-7-(tert-butyldimethylsilyloxy)-5-hydroxy-4,6-dimethyl-3-oxoheptan-2-yl benzoate 在 chromium dichloride 、 sodium periodate 、 lithium aluminium tetrahydride 、三氟甲磺酸、邻苯二甲酸二甲酯、 camphor-10-sulfonic acid 、 2,2,6,6-tetramethylpiperidinyl-lithium 、 potassium hydride 、 lithium bromide 作用下，以四氢呋喃、甲醇、二氯甲烷为溶剂，反应 38.37h，生成 (3Z,5S,6S,7S,8R,9R,11Z,13S,14R,15S)-14-(t-butyldimethylsilyloxy)-6,16-bis(p-methoxybenzyloxy)-9-(hydroxymethyl)-5,7,11,13,15-pentamethylhexadeca-1,3,11-trien-8-ol

参考文献：

名称：

使用手性酮的硼介导的醛醇缩合反应合成抗微管剂（+）-Discodermolide。

摘要：

具有与紫杉醇相似的作用机理，标题化合物1是癌症化学疗法发展中特别有希望的候选者。这种基于立体控制的醛醇缩合反应的有效合成方法应有助于克服稀有海绵来源的稀缺天然物质1的供应。

DOI：

10.1002/(sici)1521-3773(20000117)39:2<377::aid-anie377>3.0.co;2-e

点击查看最新优质反应信息

文献信息

Total Synthesis of the Antimicrotubule Agent (+)-Discodermolide Using Boron-Mediated Aldol Reactions of Chiral Ketones

作者：Ian Paterson、Gordon J. Florence、Kai Gerlach、Jeremy P. Scott

DOI：10.1002/(sici)1521-3773(20000117)39:2<377::aid-anie377>3.0.co;2-e

日期：2000.1.17

With a similar mechanism of action to taxol, the title compound 1 is a particularly promising candidate for development in cancer chemotherapy. This efficient synthesis, based on stereocontrolled aldol reactions, should help to overcome the scarce natural supply of 1 from the rare sponge source.

具有与紫杉醇相似的作用机理，标题化合物1是癌症化学疗法发展中特别有希望的候选者。这种基于立体控制的醛醇缩合反应的有效合成方法应有助于克服稀有海绵来源的稀缺天然物质1的供应。
A Second-Generation Total Synthesis of (+)-Discodermolide: The Development of a Practical Route Using Solely Substrate-Based Stereocontrol

作者：Ian Paterson、Oscar Delgado、Gordon J. Florence、Isabelle Lyothier、Matthew O'Brien、Jeremy P. Scott、Natascha Sereinig

DOI：10.1021/jo048534w

日期：2005.1.1

subunits, aldehyde 9 (C1−C5), ester 40 (C9−C16), and aldehyde 13 (C17−C24), was established via a boron-mediated aldol reaction of ethyl ketone 15 and formaldehyde, followed by hydroxyl-directed reduction to give 1,3-diol 14. Alternatively, a surrogate aldehyde 22 was employed for formaldehyde in this aldol reaction, leading to the β-hydroxy aldehyde 20 as a common building block, corresponding to the discodermolide

复杂的聚酮化合物（+）-discodermolide（一种有希望的海绵状抗癌剂）的新颖的全合成方法，以24个线性步骤（共35个步骤）完成了7.8％的总收率。第二代方法设计为仅依靠底物控制来引入所需的立体化学，而无需使用所有手性试剂或助剂。常见的1,2-抗-2,3- -syn立体三元组存在于以下三个亚基中：醛9（C 1 -C 5），酯40（C 9 -C 16）和醛13（C 17 -C 24）），是通过乙酮15和甲醛的硼介导的醛醇缩合反应建立的，然后通过羟基直接还原得到1,3-二醇14。备选地，在该醛醇缩合反应中，将替代醛22用于甲醛，从而导致β-羟基醛20作为共同的结构单元，对应于二茂铁立体异构体。关键片段的结合是通过在Felkin-Anh控制下酯40和醛13的锂介导的抗羟醛缩合反应实现的，以提供（16 S，17 S）加合物51和烯酮10之间的硼介导的羟醛缩合反应。和醛9，利用前所未有的远程1
Synthesis of novel discodermolide analogues with modified hydrogen-bonding donor/acceptor sites

作者：Ian Paterson、Oscar Delgado

DOI：10.1016/j.tetlet.2003.09.172

日期：2003.12

A series of novel structural analogues of the potent microtubule-stabilizing anticancer agent discodermolide were synthesised, with modifications in the C16-C20 region to create new oxygenated H-bonding donor/acceptor sites for tubulin binding. By starting from an advanced C9-C24 intermediate, fully synthetic discodermolide analogues, incorporating either an additional hydroxyl group 3, an oxetane 4 or a cyclic carbonate 5, were obtained in 10 or 11 steps by using a versatile aldol construction of the C6-C7 bond. (C) 2003 Elsevier Ltd. All rights reserved.
A Practical Synthesis of (+)-Discodermolide and Analogues: Fragment Union by Complex Aldol Reactions

作者：Ian Paterson、Gordon J. Florence、Kai Gerlach、Jeremy P. Scott、Natascha Sereinig

DOI：10.1021/ja011211m

日期：2001.10.1

substrate-controlled, boron-mediated, aldol reactions of the chiral ethyl ketones 10, 11, and 12. Key fragment coupling reactions were a lithium-mediated, anti-selective, aldol reaction of aryl ester 8 (under Felkin-Anh induction from the aldehyde component 9), followed by in situ reduction to produce the 1,3-diol 40, and a (+)-diisopinocampheylboron chloride-mediated aldol reaction of methyl ketone 7 (overturning

(+)-discodermolide (1) 的实用立体控制合成已完成，总产率为 10.3%（最长线性序列为 23 步）。C(1)-C(6) (7)、C(9)-C(16) (8) 和 C(17)-C(24) (9) 亚基的绝对立体化学是通过底物建立的 -手性乙基酮 10、11 和 12 的受控、硼介导的羟醛反应。关键片段偶联反应是芳基酯 8 的锂介导的、抗选择性的羟醛反应（在醛组分的 Felkin-Anh 诱导下） 9)，然后原位还原产生 1,3-二醇 40，和 (+)-二异松蒎基氯化硼介导的甲基酮 7 羟醛反应（颠覆醛组分 52 的固有底物诱导）得到（ 7S)-加合物 58。