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喹啉
水杨醛
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(7S,10R,11S,12S,19S,Z)-7,11-bis(tert-butyldimethylsilyloxy)-2,2,3,3,8,8,10,12,16,21,21,22,22-tridecamethyl-19-((E)-1-(2-methylthiazol-4-yl)prop-1-en-2-yl)-4,20-dioxa-3,21-disilatricos-16-en-9-one | 193146-51-9

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

(7S,10R,11S,12S,19S,Z)-7,11-bis(tert-butyldimethylsilyloxy)-2,2,3,3,8,8,10,12,16,21,21,22,22-tridecamethyl-19-((E)-1-(2-methylthiazol-4-yl)prop-1-en-2-yl)-4,20-dioxa-3,21-disilatricos-16-en-9-one

英文别名

(3S,6R,7S,8S,12Z,15S,16E)-1,3,7,15-tetrakis{[tert-butyl(dimethyl)silyl]oxy}-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)heptadeca-12,16-dien-5-one；(3S,6S,7S,8S,12Z,15S,16E)-1,3,7,15-Tetra[(tert-butyldimethylsilyl)oxy]-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-12,16-heptadecadien-5-one；(3S,6R,7S,8S,12Z,15S,16E)-1,3,7,15-tetrakis[[tert-butyl(dimethyl)silyl]oxy]-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)heptadeca-12,16-dien-5-one

(7S,10R,11S,12S,19S,Z)-7,11-bis(tert-butyldimethylsilyloxy)-2,2,3,3,8,8,10,12,16,21,21,22,22-tridecamethyl-19-((E)-1-(2-methylthiazol-4-yl)prop-1-en-2-yl)-4,20-dioxa-3,21-disilatricos-16-en-9-one化学式

CAS

193146-51-9

化学式

C₅₁H₁₀₁NO₅SSi₄

mdl

——

分子量

952.775

InChiKey

OCGGWJZENCFVKE-PPXDMVPQSA-N

BEILSTEIN

——

EINECS

——

物化性质

溶解度：

可溶于丙酮、氯仿、二氯甲烷、乙酸乙酯

计算性质

辛醇/水分配系数(LogP)：

16.81
重原子数：

62
可旋转键数：

27
环数：

1.0
sp3杂化的碳原子比例：

0.84
拓扑面积：

95.1
氢给体数：

0
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
——	(7S,10R,11S,12S,19S,Z)-7-(tert-butyldimethylsilyloxy)-11-hydroxy-2,2,3,3,8,8,10,12,16,21,21,22,22-tridecamethyl-19-((E)-1-(2-methylthiazol-4-yl)prop-1-en-2-yl)-4,20-dioxa-3,21-disilatricos-16-en-9-one	193146-49-5	C₄₅H₈₇NO₅SSi₃	838.512
——	(4S,5S,6S,7S,10Z,13S,14E)-13-[(tert-Butyldimethylsilyl)oxy]-2-[(4R)-2,2-dimethyl-1,3-dioxan-4-yl]-5-hydroxy-2,4,6,10,14-pentamethyl-15-(1,3-thiazol-4-yl)-10,14-pentadecadien-3-one	210690-87-2	C₃₆H₆₃NO₅SSi	650.051
4-[(1E,3S,5Z,8R/S,10S)-3,11-二-{[叔-丁基(二甲基)硅烷基]氧基}-2,6,10-三甲基-十一碳-1,5-二烯基]-2-甲基-1,3-噻唑	(2S,6Z,9S,10E)-1,9-Bis[(1,1-dimethylethyl)dimethylsilyloxy]-11-(2-methylthiazol-4-yl)-2,6,10-trimethyl-undeca-6,10-diene	210690-85-0	C₃₀H₅₇NO₂SSi₂	552.025
——	(2E,6E)-(S)-5-(tert-butyl-dimethyl-silanyloxy)-2-[(S)-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pentyl]-6-methyl-7-(2-methyl-thiazol-4-yl)-hepta-2,6-dien-1-ol	226940-55-2	C₃₀H₅₇NO₃SSi₂	568.024
——	(2S,6Z,9S,10E)-9-{[tert-butyl(dimethyl)silyl]oxy}-2,6,10-trimethyl-11-(2-methyl-1,3-thiazol-4-yl)undeca-6,10-dienal	193146-27-9	C₂₄H₄₁NO₂SSi	435.747
(+)-(2S,6Z,9S,10E)-9-{[叔-丁基(二甲基)硅烷基]氧基}-2,6,10-三甲基-11-(2-甲基-1,3-噻唑-4-基)-十一碳-6,10-二烯-1-醇	(2S,6Z,9S,10E)-9-[(1,1-Dimethylethyl)dimethylsilyloxy]-11-(2-methylthiazol-4-yl)-2,6,10-trimethyl-undeca-6,10-dien-1-ol	210690-99-6	C₂₄H₄₃NO₂SSi	437.762
——	(2E,6E)-(S)-5-(tert-butyl-dimethyl-silanyloxy)-2-[(S)-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pentyl]-6-methyl-7-(2-methyl-thiazol-4-yl)-hepta-2,6-dienoic acid methyl ester	226940-54-1	C₃₁H₅₇NO₄SSi₂	596.035
——	(4Z,7S,8E)-7-[tert-butyl(dimethyl)silyl]oxy-4,8-dimethyl-9-(2-methyl-1,3-thiazol-4-yl)nona-4,8-dien-1-ol	193146-44-0	C₂₁H₃₇NO₂SSi	395.682
——	(2E,6E)(5S)-6-methyl-7-(2-methyl-(1,3-thiazol-4-yl))-2-prop-2-enyl-5-(1,1,2,2-tetramethyl-1-silapropoxy)hepta-2,6-dien-1-ol	193146-41-7	C₂₁H₃₅NO₂SSi	393.666
(-)-(2Z,5S,6E)-5-{[叔-丁基(二甲基)硅烷基]氧基}-2,6-二甲基-7-(2-甲基-1,3-噻唑-4-基)庚-2,6-二烯-1-醇	(-)-(2Z,5S,6E)-5-{[tert-butyl(dimethyl)silyl]oxy}-2,6-dimethyl-7-(2-methyl-1,3-thiazol-4-yl)hepta-2,6-dien-1-ol	218614-16-5	C₁₉H₃₃NO₂SSi	367.628
——	tert-Butyldimethylsilyl {(1S,3Z)-4-iodo-1-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)-1-ethenyl]-3-pentenyl} ether	210690-66-7	C₁₈H₃₀INOSSi	463.498
——	ethyl (2Z,5S,6E)-5-{[tert-butyl(dimethyl)silyl]oxy}-2,6-dimethyl-7-(2-methyl-1,3-thiazol-4-yl)hepta-2,6-dienoate	218614-04-1	C₂₁H₃₅NO₃SSi	409.665
——	(S)-2-methyl-4-([E]-2'-methyl-3'-(tert-butyldimethylsilanyloxy)hexa-1',5'-dienyl)thiazole	188730-05-4	C₁₇H₂₉NOSSi	323.575
——	(3S,4E)-1,3-Di-(tert-butyldimethylsilyloxy)-4-methyl-5-(2-methyl-1,3-thiazol-4-yl)-4-pentene	188899-13-0	C₂₂H₄₃NO₂SSi₂	441.826
——	(3S,4E)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-methyl-5-(2-methyl-1,3-thiazol-4-yl)pent-4-en-1-al	188730-08-7	C₁₆H₂₇NO₂SSi	325.547
4-[(1E,3S,5Z,8R/S,10S)-3,11-二-{[叔-丁基(二甲基)硅烷基]氧基}-2,6,10-三甲基-8-(苯磺酰基)十一碳-1,5-二烯基]-2-甲基-1,3-噻唑	4-[(1E,3S,5Z,8R/S,10S)-3,11-bis{[tert-butyl(dimethyl)silyl]oxy}-2,6,10-trimethyl-8-(phenylsulfonyl)undeca-1,5-dienyl]-2-methyl-1,3-thiazole	308357-81-5	C₃₆H₆₁NO₄S₂Si₂	692.188
(-)-(3S,4E)-3-{[叔-丁基(二甲基)硅烷基]氧基}-4-甲基-5-(2-甲基-1,3-噻唑-4-基)戊-4-烯-1-醇	(3S,4E)-3-(tert-butyldimethylsilyloxy)-4-methyl-5-(2-methyl-1,3-thiazol-4-yl)pent-4-en-1-ol	188899-14-1	C₁₆H₂₉NO₂SSi	327.563
——	(4S)-4-benzyl-3-[(2S,6E,9S,10E)-9-[tert-butyl(dimethyl)silyl]oxy-6-(chloromethyl)-2,10-dimethyl-11-(2-methyl-1,3-thiazol-4-yl)undeca-6,10-dienoyl]-1,3-oxazolidin-2-one	355009-08-4	C₃₄H₄₉ClN₂O₄SSi	645.379
——	(4S)-4-benzyl-3-[(E,2S,9S)-9-[tert-butyl(dimethyl)silyl]oxy-7-hydroxy-2,10-dimethyl-6-methylidene-11-(2-methyl-1,3-thiazol-4-yl)undec-10-enoyl]-1,3-oxazolidin-2-one	355009-06-2	C₃₄H₅₀N₂O₅SSi	626.933

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	(5S,8R,9S,10S,17S,Z)-9-(tert-butyldimethylsilyloxy)-5-(2-hydroxyethyl)-2,2,3,3,6,6,8,10,14,19,19,20,20-tridecamethyl-17-((E)-1-(2-methylthiazol-4-yl)prop-1-en-2-yl)-4,18-dioxa-3,19-disilahenicos-14-en-7-one	193146-53-1	C₄₅H₈₇NO₅SSi₃	838.512
——	(12Z,16E)-(3S,6R,7S,8S,15S)-3,7,15-tris-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8,12,16-hexamethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-heptadeca-12,16-dienoic acid	193146-63-3	C₄₅H₈₅NO₆SSi₃	852.495
——	(3S,6R,7S,8S,12Z,15S,16E)-3,7-bis{[tert-butyl(dimethyl)silyl]oxy}-15-hydroxy-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxoheptadeca-12,16-dienoic acid	193146-26-8	C₃₉H₇₁NO₆SSi₂	738.233
(4S,7R,8S,9S,13Z,16S)-4,8-二-{[叔-丁基(二甲基)硅烷基]氧基}-5,5,7,9,13-五甲基-16-[(E)-1-甲基-2-(2-甲基-1,3-噻唑-4-基)乙烯基]氧代环己癸-13-烯-2,6-二酮	(4S,7R,8S,9S,13Z,16S)-4,8-bis{[tert-butyl(dimethyl)silyl]oxy}-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]oxacyclohexadec-13-ene-2,6-dione	189453-35-8	C₃₉H₆₉NO₅SSi₂	720.218
埃博霉素	epothilone D	189453-10-9	C₂₇H₄₁NO₅S	491.692
埃博霉素B	epothilone B	152044-54-7	C₂₇H₄₁NO₆S	507.692
——	(1R,3S,7S,10R,11S,12S,16S)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione	——	C₂₇H₄₁NO₆S	507.692
——	[4S-[4R,7S,8R,9R,15R*(E)]]-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-1-aza-13(Z)-cyclohexadecene-2,6-dione	219989-87-4	C₂₇H₄₂N₂O₄S	490.707
——	(3S,6R,7S,8S)-11-((2R,3S)-3-((S,E)-2-amino-3-methyl-4-(2-methylthiazol-4-yl)but-3-enyl)-2-methyloxiran-2-yl)-3,7-dihydroxy-4,4,6,8-tetramethyl-5-oxoundecanoic acid	219990-25-7	C₂₇H₄₄N₂O₆S	524.722
——	(3S,6R,7S,8S)-11-((2R,3S)-3-((S,E)-2-azido-3-methyl-4-(2-methylthiazol-4-yl)but-3-enyl)-2-methyloxiran-2-yl)-3,7-dihydroxy-4,4,6,8-tetramethyl-5-oxoundecanoic acid	219990-23-5	C₂₇H₄₂N₄O₆S	550.72

反应信息

作为反应物：

描述：

(7S,10R,11S,12S,19S,Z)-7,11-bis(tert-butyldimethylsilyloxy)-2,2,3,3,8,8,10,12,16,21,21,22,22-tridecamethyl-19-((E)-1-(2-methylthiazol-4-yl)prop-1-en-2-yl)-4,20-dioxa-3,21-disilatricos-16-en-9-one 在 sodium chlorite 、四(三苯基膦)钯、 sodium azide 、 sodium dihydrogenphosphate dihydrate 、 2,4,6-三氯苯甲酰氯、 D(+)-10-樟脑磺酸、四丁基氟化铵、 1-羟基苯并三唑、戴斯-马丁氧化剂、盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺、三乙胺、间氯过氧苯甲酸、三氟乙酸、三甲基膦作用下，以四氢呋喃、吡啶、甲醇、二氯甲烷、氯仿、水、 N,N-二甲基甲酰胺、乙腈、叔丁醇为溶剂，反应 44.25h，生成伊沙匹隆

参考文献：

名称：

[EN] PROCESS FOR THE PREPARATION OF (1S,3S,7S,10R,11S,12S,16R)-7,11-DIHYDROXY-8,8,10,12,16-PENTAMETHYL-3-[(1E)-1-METHYL-2-(2-METHYL-4-THIAZOLYL)ETHENYL]-17-OXA-4-AZABICYCLO[14.1.0]HEPTADECANE-5,9-DIONE AND INTERMEDIATES THEREOF
[FR] PROCÉDÉ DE PRÉPARATION DE (1S,3S,7S,10R,11S,12S,16R)-7,11-DIHYDROXY-8,8,10,12,16-PENTAMÉTHYL-3-[(1E)-1-MÉTHYL-2-(2-MÉTHYL-4-THIAZOLYL)ÉTHÉNYL]-17-OXA-4-AZABICYCLO[14.1.0]HEPTADÉCANE-5,9-DIONE ET DE SES INTERMÉDIAIRES

摘要：

公开号：

WO2015087351A3
作为产物：

描述：

3-(叔丁基-二甲基-硅烷基OXY)-丙醛在 2,6-二甲基吡啶、硼烷四氢呋喃络合物、 N-对甲苯磺酰基-D-缬氨酸、 lithium diisopropyl amide 作用下，以四氢呋喃、正己烷、二氯甲烷、正戊烷为溶剂，反应 19.5h，生成 (7S,10R,11S,12S,19S,Z)-7,11-bis(tert-butyldimethylsilyloxy)-2,2,3,3,8,8,10,12,16,21,21,22,22-tridecamethyl-19-((E)-1-(2-methylthiazol-4-yl)prop-1-en-2-yl)-4,20-dioxa-3,21-disilatricos-16-en-9-one

参考文献：

名称：

埃博霉素B和D的总合成。

摘要：

从光学纯的（S）-苹果酸和（R）-3-羟基-2-甲基丙酸甲酯开始，描述了微管稳定的抗肿瘤药物埃博霉素B和D的总合成。通过偶联三个片段C1-C6（片段D），C7-C10（片段C）和C11-C21（片段B），合成高度收敛。关键步骤是两个立体选择性Wittig型烯烃生成12,13-和16,17-双键，对映选择性Mukaiyama aldol加成以合成片段D，以及砜阴离子烯丙基碘烷基化以连接片段B和C。最后是片段D通过羟醛加成连接到B + C片段。

DOI：

10.1021/jo0007480

点击查看最新优质反应信息

文献信息

Total Syntheses of Epothilones A and B via a Macrolactonization-Based Strategy

作者：K. C. Nicolaou、S. Ninkovic、F. Sarabia、D. Vourloumis、Y. He、H. Vallberg、M. R. V. Finlay、Z. Yang

DOI：10.1021/ja971110h

日期：1997.8.1

The total syntheses of epothilones A (1) and B (2) and several analogues thereof are described. The reported strategy relies on a macrolactonization approach and features selective epoxidation of the macrocycle double bond in precursors 3 and 4 (Scheme 1), respectively, as well as high convergency and flexibility. Building blocks 9−12 and 15 were constructed by asymmetric processes and coupled via

描述了埃坡霉素 A (1) 和 B (2) 及其几种类似物的全合成。报道的策略依赖于大环内酯化方法，并分别具有前体 3 和 4 中大环双键的选择性环氧化（方案 1），以及高收敛性和灵活性。构建块 9-12 和 15 是通过不对称过程构建的，并通过 Wittig、羟醛和大环内酯化反应偶联，以相对较短的路线提供埃坡霉素及其几种类似物的基本骨架。利用通过立体选择性 Wittig 反应获得的中间体 14 及其与 SAMP 腙13 的 Enders 偶联（方案 8），
Synthesis of Epothilones: Stereoselective Routes to Epothilone B

作者：Dieter Schinzer、Armin Bauer、Jennifer Schieber

DOI：10.1055/s-1998-1794

日期：1998.8

In connection with our studies of the total syntheses of epothilones we report our efforts on the syntheses of epothilone B using a macro-lactonization and a metathesis approach. Key reaction for the solution of the acyclic stereoselection is a stereoselective aldol reaction.

在我们的埃博霉素全合成研究中，我们报道了采用大环内酯化和复分解方法合成埃博霉素B的努力。解决非环状立体选择性的关键反应是一项立体选择性的羟醛反应。
Total Synthesis of Epothilones B and D

作者：Richard E. Taylor、Yue Chen

DOI：10.1021/ol010094x

日期：2001.7.1

[reaction: see text] A highly convergent total synthesis of the natural products epothilone B and D is described. The route is highlighted by efficient generation of a C12-C13 trisubstituted olefin which exploits a sequential Nozaki-Hiyama-Kishi coupling and a stereoselective thionyl chloride rearrangement.

[反应：见正文]描述了天然产物埃坡霉素B和D的高度收敛的全合成。有效产生C12-C13三取代的烯烃是该路线的重点，该烯烃利用了连续的Nozaki-Hiyama-Kishi偶联和立体选择性的亚硫酰氯重排。
Synthesis of 16-desmethylepothilone B: improved methodology for the rapid, highly selective and convergent construction of epothilone B and analogues

作者：K. C. Nicolaou、David Hepworth、M. Ray V. Finlay、N. Paul King、Barbara Werschkun、Antony Bigot

DOI：10.1039/a809954e

日期：——

During a synthesis of 16-desmethylepothilone B new methods for the convergent and highly stereoselective synthesis of epothilone B and analogues were developed.

在合成16-去甲基埃博霉素B的过程中，研究人员开发出了埃博霉素B及其类似物的高效立体选择性合成新方法。
Syntheses of (−)-Epothilone B

作者：Dieter Schinzer、Armin Bauer、Jennifer Schieber

DOI：10.1002/(sici)1521-3765(19990903)5:9<2492::aid-chem2492>3.0.co;2-r

日期：1999.9.3