tert-butyl (1S,3S,7S,10S,11S,14R,21S,26R,27R,28R,29S,30S)-29-[tert-butyl(dimethyl)silyl]oxy-21-[(2R,3S)-2,3-dimethyl-4-(prop-2-enoxycarbonylamino)butyl]-11,30-dimethyl-16-methylidene-20-oxo-11-triethylsilyloxy-32,33,34,35,36-pentaoxaheptacyclo[25.4.1.11,28.13,7.17,10.110,14.021,26]hexatriacont-24-ene-24-carboxylate | 212689-92-4

分子结构分类

有机化合物 - 有机杂环化合物 - 氧杂环己烷

中文名称

——

中文别名

——

英文名称

tert-butyl (1S,3S,7S,10S,11S,14R,21S,26R,27R,28R,29S,30S)-29-[tert-butyl(dimethyl)silyl]oxy-21-[(2R,3S)-2,3-dimethyl-4-(prop-2-enoxycarbonylamino)butyl]-11,30-dimethyl-16-methylidene-20-oxo-11-triethylsilyloxy-32,33,34,35,36-pentaoxaheptacyclo[25.4.1.11,28.13,7.17,10.110,14.021,26]hexatriacont-24-ene-24-carboxylate

英文别名

——

tert-butyl (1S,3S,7S,10S,11S,14R,21S,26R,27R,28R,29S,30S)-29-[tert-butyl(dimethyl)silyl]oxy-21-[(2R,3S)-2,3-dimethyl-4-(prop-2-enoxycarbonylamino)butyl]-11,30-dimethyl-16-methylidene-20-oxo-11-triethylsilyloxy-32,33,34,35,36-pentaoxaheptacyclo[25.4.1.11,28.13,7.17,10.110,14.021,26]hexatriacont-24-ene-24-carboxylate化学式

CAS

212689-92-4

化学式

C₆₁H₁₀₃NO₁₂Si₂

mdl

——

分子量

1098.66

InChiKey

AJPZZTBUPCXBMW-MJKDQCOBSA-N

BEILSTEIN

——

EINECS

——

计算性质

辛醇/水分配系数(LogP)：

13.96
重原子数：

76
可旋转键数：

19
环数：

7.0
sp3杂化的碳原子比例：

0.85
拓扑面积：

146
氢给体数：

1
氢受体数：

12

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
——	tert-butyl 4-[(4R,5R)-5-[(1S,2S)-1-[tert-butyl(dimethyl)silyl]oxy-5-[(4S,6S,8S,10R,13S)-10-[(9R,10S)-9,10-dimethyl-2,7-dimethylidene-6-oxo-11-(prop-2-enoxycarbonylamino)undecyl]-13-hydroxy-13-methyl-5,7,9-trioxadispiro[5.1.58.26]pentadecan-4-yl]-2-methyl-4-oxopentyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-2-methylidenebutanoate	212689-90-2	C₅₈H₉₇NO₁₄Si	1060.49
——	tert-butyl 4-[(1R,2S,3S,5S,7R)-2-[tert-butyl(dimethyl)silyl]oxy-5-[[(4S,6S,8S,10R,13S)-10-[(9R,10S)-9,10-dimethyl-2,7-dimethylidene-6-oxo-11-(prop-2-enoxycarbonylamino)undecyl]-13-methyl-13-triethylsilyloxy-5,7,9-trioxadispiro[5.1.58.26]pentadecan-4-yl]methyl]-3-methyl-6,8-dioxabicyclo[3.2.1]octan-7-yl]-2-methylidene-3-methylsulfonyloxybutanoate	261713-03-5	C₆₂H₁₀₇NO₁₅SSi₂	1194.77
——	prop-2-enyl N-[(2S,3R)-10-[[(4S,6S,8S,10R,13S)-4-[(4S,5S)-5-[tert-butyl(dimethyl)silyl]oxy-5-[(4R,5R)-5-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-methyl-2-oxopentyl]-13-hydroxy-13-methyl-5,7,9-trioxadispiro[5.1.58.26]pentadecan-10-yl]methyl]-6-hydroxy-2,3-dimethyl-5-methylideneundec-10-enyl]carbamate	212690-23-8	C₅₁H₈₉NO₁₂Si	936.353
——	(4S,5S)-5-[tert-butyl(dimethyl)silyl]oxy-5-[(4R,5R)-5-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-1-[(4S,6S,8S,10R,13S)-13-hydroxy-10-(6-hydroxy-2-methylidenehexyl)-13-methyl-5,7,9-trioxadispiro[5.1.58.26]pentadecan-4-yl]-4-methylpentan-2-one	212689-86-6	C₄₅H₈₄O₁₀Si₂	841.327
——	{(2S,6S,8S,10R,13S)-13-(tert-Butyl-dimethyl-silanyloxy)-10-[6-(4-methoxy-benzyloxy)-2-methylene-hexyl]-13-methyl-1,7,9-trioxa-dispiro[5.1.5.2]pentadec-2-yl}-methanol	212690-07-8	C₃₅H₅₈O₇Si	618.927
——	[(2R,5S,6S,8S,10S)-5-(tert-Butyl-dimethyl-silanyloxy)-10-(tert-butyl-dimethyl-silanyloxymethyl)-5-methyl-1,7,9-trioxa-dispiro[5.1.5.2]pentadec-2-yl]-acetaldehyde	212689-81-1	C₂₈H₅₄O₆Si₂	542.904
——	(2R,5S,6S,8S,10S)-10-[1,3]Dithian-2-ylmethyl-2-[6-(4-methoxy-benzyloxy)-2-methylene-hexyl]-5-methyl-1,7,9-trioxa-dispiro[5.1.5.2]pentadecan-5-ol	212689-84-4	C₃₃H₅₀O₆S₂	606.888

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	tert-butyl (1S,3S,7S,10S,11S,14R,23S,24R,26S,31R,32R,33S,34S,35S)-11,34-dihydroxy-11,23,24,35-tetramethyl-16-methylidene-37,38,39,40,41-pentaoxa-21-azaoctacyclo[30.4.1.11,33.13,7.17,10.110,14.020,26.026,31]hentetraconta-20,29-diene-29-carboxylate	212690-27-2	C₄₅H₆₉NO₉	768.044

反应信息

作为反应物：

描述：

tert-butyl (1S,3S,7S,10S,11S,14R,21S,26R,27R,28R,29S,30S)-29-[tert-butyl(dimethyl)silyl]oxy-21-[(2R,3S)-2,3-dimethyl-4-(prop-2-enoxycarbonylamino)butyl]-11,30-dimethyl-16-methylidene-20-oxo-11-triethylsilyloxy-32,33,34,35,36-pentaoxaheptacyclo[25.4.1.11,28.13,7.17,10.110,14.021,26]hexatriacont-24-ene-24-carboxylate 在吡啶、氢氟酸作用下，以四氢呋喃为溶剂，以94%的产率得到

参考文献：

名称：

Total Synthesis of Pinnatoxin A

摘要：

DOI：

10.1021/ja981257o
作为产物：

描述：

[(2R,5S,6S,8S,10S)-5-(tert-Butyl-dimethyl-silanyloxy)-10-(tert-butyl-dimethyl-silanyloxymethyl)-5-methyl-1,7,9-trioxa-dispiro[5.1.5.2]pentadec-2-yl]-acetaldehyde 在吡啶、三乙烯二胺、咪唑、 2,6-二甲基吡啶、 chromium dichloride 、六甲基磷酰三胺、正丁基锂、草酰氯、 bispyridinyl ligand 、 TEA 、氢氟酸、四丁基氟化铵、碘、叔丁基锂、戴斯-马丁氧化剂、二甲基亚砜、三乙胺、三苯基膦、三氟乙酸、 2,3-二氯-5,6-二氰基-1,4-苯醌、 nickel dichloride 作用下，以四氢呋喃、乙醚、十二烷、二氯甲烷、二甲基亚砜、苯为溶剂，生成 tert-butyl (1S,3S,7S,10S,11S,14R,21S,26R,27R,28R,29S,30S)-29-[tert-butyl(dimethyl)silyl]oxy-21-[(2R,3S)-2,3-dimethyl-4-(prop-2-enoxycarbonylamino)butyl]-11,30-dimethyl-16-methylidene-20-oxo-11-triethylsilyloxy-32,33,34,35,36-pentaoxaheptacyclo[25.4.1.11,28.13,7.17,10.110,14.021,26]hexatriacont-24-ene-24-carboxylate

参考文献：

名称：

Total Synthesis of Pinnatoxin A

摘要：

DOI：

10.1021/ja981257o

点击查看最新优质反应信息

文献信息

Total Synthesis of Pinnatoxin A

作者：John A. McCauley、Kazuo Nagasawa、Peter A. Lander、Steven G. Mischke、Marcus A. Semones、Yoshito Kishi

DOI：10.1021/ja981257o

日期：1998.8.1

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