首页分子通化学资讯化学百科反应查询关于我们

请输入关键词

历史搜索

热门化合物HOT

喹啉
水杨醛
二溴甲烷
谷胱甘肽
L-乳酸
苯巴比妥
辣椒碱
非那明
百草枯
联苯烯

(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

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

(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

英文别名

(3S,6R,7S,8S,12Z,15S,16E)-3,7,15-tris{[tert-butyl(dimethyl)silyl]oxy}-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxoheptadeca-12,16-dienoic acid；(3S,6R,7S,8S,12Z,15S,16E)-3,7,15-tris(tert-butyldimethylsilyloxy)-4,4,6,8,12,16-hexamethyl-17-(2-methylthiazol-4-yl)-5-oxoheptadeca-12,16-dienoic acid；(3S,6R,7S,8S,12Z,15S,16E)-3,7,15-tris[[tert-butyl(dimethyl)silyl]oxy]-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxoheptadeca-12,16-dienoic acid

(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化学式

CAS

193146-63-3

化学式

C₄₅H₈₅NO₆SSi₃

mdl

——

分子量

852.495

InChiKey

GWEYNQSYTRXNRT-VPOHWXGHSA-N

BEILSTEIN

——

EINECS

——

物化性质

沸点：

761.2±60.0 °C(Predicted)
密度：

0.979±0.06 g/cm3(Predicted)
溶解度：

可溶于丙酮、氯仿、二氯甲烷、乙醇、乙酸乙酯

计算性质

辛醇/水分配系数(LogP)：

13.87
重原子数：

56
可旋转键数：

24
环数：

1.0
sp3杂化的碳原子比例：

0.8
拓扑面积：

123
氢给体数：

1
氢受体数：

8

SDS

SDS：43996357896c22adcfc840f248736703

查看

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
——	(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
——	(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	C₅₁H₁₀₁NO₅SSi₄	952.775
——	(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
——	(3S,6R,7S,8S,12Z,15S,16E)-15-(tert-butyldimethylsiloxy)-3,7-dihydroxy-4,4,6,8,12,16-hexamethyl-17-(2-methylthiazol-4-yl)-5-oxaheptadeca-12,16-dienic acid	1236206-72-6	C₃₃H₅₇NO₆SSi	623.97
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
——	(4R,5S,6S,10Z,13S,14E)-13-(tert-butyldimethylsiloxy)-2-{(7S)-5,5-dimethyl-4,6-dioxaspiro[2.5]oct-7-yl}-5-hydroxy-2,4,6,10,14-pentamethyl-15-(2-methylthiazol-4-yl)pentadeca-10,14-dien-3-one	1236206-70-4	C₃₈H₆₅NO₅SSi	676.089
——	(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
——	(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
——	4-[(1E,3S,5Z,10S)-3-(tert-butyldimethylsiloxy)-2,6,10-trimethyl-11-(tetrahydro-2H-pyran-2-yloxy)undeca-1,5-dienyl]-2-methylthiazole	1236206-69-1	C₂₉H₅₁NO₃SSi	521.88
——	(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
——	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
——	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
——	(S)-2-methyl-4-([E]-2'-methyl-3'-(tert-butyldimethylsilanyloxy)hexa-1',5'-dienyl)thiazole	188730-05-4	C₁₇H₂₉NOSSi	323.575
——	(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)-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-{[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
——	2-[(2S,3E)-2-(tert-butyldimethylsiloxy)-3-methyl-4-(2-methylthiazol-4-yl)but-3-enyl]-1-[(4S)-4-methyl-5-(tetrahydro-2H-pyran-2-yloxy)pentyl]cyclopropyl methanesulphonate	1236207-66-1	C₃₀H₅₃NO₆S₂Si	615.971
——	(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
——	(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
——	(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
——	[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-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：

(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 在四(三苯基膦)钯、 sodium azide 、 2,4,6-三氯苯甲酰氯、四丁基氟化铵、 1-羟基苯并三唑、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、二氯甲烷、氯仿、水、 N,N-二甲基甲酰胺、乙腈为溶剂，反应 35.75h，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、 sodium chlorite 、 disodium hydrogenphosphate 、 2,3-二甲基-2-丁烯、硼烷四氢呋喃络合物、 camphor-10-sulfonic acid 、 N-对甲苯磺酰基-D-缬氨酸、戴斯-马丁氧化剂作用下，以甲醇、二氯甲烷、水、叔丁醇为溶剂，反应 15.67h，生成 (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

参考文献：

名称：

Easy access to the epothilone family-synthesis of epothilone B

摘要：

An easy access to four out of five naturally occurring epothilones (A-E, 1-5) is reported. Key steps are an enantioselective Mukaiyama type aldol reaction, (E)- and (Z)-selective olefinations, and a sulfone alkylation. (C) 1998 Elsevier Science Ltd. All rights reserved.

DOI：

10.1016/s0040-4039(98)02026-7

点击查看最新优质反应信息

文献信息

Total Syntheses of Epothilones B and D

作者：Johann Mulzer、Andreas Mantoulidis、Elisabeth Öhler

DOI：10.1021/jo0007480

日期：2000.11.1

described, starting from optically pure (S)-malic acid and methyl (R)-3-hydroxy-2-methylpropionate. The synthesis is highly convergent by coupling the three fragments C1-C6 (fragment D), C7-C10 (fragment C), and C11-C21 (fragment B). Key steps are two stereoselective Wittig type olefinations to generate the 12,13- and 16,17-double bonds, an enantioselective Mukaiyama aldol addition to synthesize fragment

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。
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），
Total synthesis of epothilone D by sixfold ring cleavage of cyclopropanol intermediates

作者：Alaksiej L. Hurski、Oleg G. Kulinkovich

DOI：10.1016/j.tetlet.2010.04.109

日期：2010.7

The ring-opening or ring fragmentation reactions of cyclopropanol intermediates are used in the total synthesis of epothilone D for the creation of trisubstituted double bonds, an ethyl ketone functionality, as well as for the protection of carboxylic and ester groups. Epothilone D is obtained in 1.6% overall yield (24 steps in the longest linear sequence) starting from (R)-methyl 2,3-O-isopropylideneglycerate

环丙醇中间体的开环或开环断裂反应用于埃博霉素D的全合成中，用于产生三取代的双键，乙基酮官能团以及保护羧基和酯基。从（R）-2，3- O-异亚丙基甘油酸酯开始，以1.6％的总产率（最长的线性序列中的24步）获得埃坡霉素D。关键的环丙醇中间体可通过钛（IV）催化易得的酯与格氏试剂的反应而有效地获得。
Synthesis of epothilone D with the forced application of oxycyclopropane intermediates

作者：A. L. Hurski、O. G. Kulinkovich

DOI：10.1134/s1070428011110029

日期：2011.11

The total synthesis of epothilone D with six-fold application in the intermediate stages of successive cyclopropanation — opening or cleavage of the three-membered ring was performed. These transformations underlie the new stereoselective method developed for coupling fragments C7–C12 and C13–C21 in the target molecule.

在连续的环丙烷化的中间阶段进行六次应用的埃博霉素D的全合成-打开或裂解三元环。这些转变是为偶联目标分子中的片段C 7 -C 12和C 13 -C 21而开发的新的立体选择性方法的基础。
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。