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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

(3aS,8R,9aS,10S,11aR,13aS,13bR,13cS)-6,9a,14,14-tetramethyl-2,9-dioxo-10-triethylsilyloxy-4,5,8,9,9a,10,11,11a,13b,13c-decahydro-3a,7-methanooxeto[2'',3'':5',6']benzo[1',2':3,4]cyclodeca[1,2-d][1,3]dioxole-8,13a(13H)diyl diacetate | 155588-15-1

分子结构分类

有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物

中文名称

——

中文别名

——

英文名称

(3aS,8R,9aS,10S,11aR,13aS,13bR,13cS)-6,9a,14,14-tetramethyl-2,9-dioxo-10-triethylsilyloxy-4,5,8,9,9a,10,11,11a,13b,13c-decahydro-3a,7-methanooxeto[2'',3'':5',6']benzo[1',2':3,4]cyclodeca[1,2-d][1,3]dioxole-8,13a(13H)diyl diacetate

英文别名

[(1S,5S,6R,7S,10R,12S,13S,15R)-7-acetyloxy-13,17,20,20-tetramethyl-3,14-dioxo-12-triethylsilyloxy-2,4,9-trioxapentacyclo[14.3.1.01,5.06,13.07,10]icos-16-en-15-yl] acetate

(3aS,8R,9aS,10S,11aR,13aS,13bR,13cS)-6,9a,14,14-tetramethyl-2,9-dioxo-10-triethylsilyloxy-4,5,8,9,9a,10,11,11a,13b,13c-decahydro-3a,7-methanooxeto[2'',3'':5',6']benzo[1',2':3,4]cyclodeca[1,2-d][1,3]dioxole-8,13a(13H)diyl diacetate化学式

CAS

155588-15-1

化学式

C₃₁H₄₆O₁₀Si

mdl

——

分子量

606.786

InChiKey

LLQAXTRWPRELFC-KSGSGGQMSA-N

BEILSTEIN

——

EINECS

——

物化性质

沸点：

654.0±55.0 °C(Predicted)
密度：

1.21±0.1 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

5.03
重原子数：

42
可旋转键数：

9
环数：

5.0
sp3杂化的碳原子比例：

0.81
拓扑面积：

124
氢给体数：

0
氢受体数：

10

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
——	[(1S,5S,6R,7S,10R,12S,13S,15R)-7-hydroxy-13,17,20,20-tetramethyl-3,14-dioxo-12-triethylsilyloxy-2,4,9-trioxapentacyclo[14.3.1.01,5.06,13.07,10]icos-16-en-15-yl] acetate	162238-76-8	C₂₉H₄₄O₉Si	564.748
——	[(1S,5S,6R,7S,8S,10S,11S,13R)-13-acetyloxy-7,8-dihydroxy-11,15,18,18-tetramethyl-3,12-dioxo-10-triethylsilyloxy-2,4-dioxatetracyclo[12.3.1.01,5.06,11]octadec-14-en-7-yl]methyl acetate	162088-55-3	C₃₁H₄₈O₁₁Si	624.801
——	[(1S,5S,6R,7S,10R,12S,13S,15R)-7-acetyloxy-13,17,20,20-tetramethyl-3,14,18-trioxo-12-triethylsilyloxy-2,4,9-trioxapentacyclo[14.3.1.01,5.06,13.07,10]icos-16-en-15-yl] acetate	155588-12-8	C₃₁H₄₄O₁₁Si	620.769
——	(3aS,8R,9aS,10S,12S,13S,13aR,13bS)-12,13-dihydroxy-6,9a,14,14-tetramethyl-2,9-dioxo-10-((triethylsilyl)oxy)-13-(((trimethylsilyl)oxy)methyl)-5,8,9,9a,10,11,12,13,13a,13b-decahydro-4H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxol-8-yl acetate	162088-61-1	C₃₂H₅₄O₁₀Si₂	654.946
——	(2aR,4S,4aS,6R,11S,12S,12aR,12bS)-11,12-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-4-((triethylsilyl)oxy)-3,4,4a,5,6,9,10,11,12,12a-decahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxete-6,12b(2aH)-diyl diacetate	155588-20-8	C₃₀H₄₈O₉Si	580.791
——	[(1S,5S,6R,7S,10R,12S,13S,15R)-15-hydroxy-13,17,20,20-tetramethyl-3,14,18-trioxo-12-triethylsilyloxy-2,4,9-trioxapentacyclo[14.3.1.01,5.06,13.07,10]icos-16-en-7-yl] acetate	155588-11-7	C₂₉H₄₂O₁₀Si	578.732
——	[(1S,5S,6R,7S,8S,10S,11S,13R)-7-hydroxy-7-(hydroxymethyl)-11,15,18,18-tetramethyl-8-methylsulfonyloxy-3,12-dioxo-10-triethylsilyloxy-2,4-dioxatetracyclo[12.3.1.01,5.06,11]octadec-14-en-13-yl] acetate	162088-64-4	C₃₀H₄₈O₁₂SSi	660.855
——	(2aR,4S,4aS,6R,11S,12S,12aR,12bS)-12-benzoyloxy-11-hydroxy-4a,8,13,13-tetramethyl-5-oxo-4-triethylsilyloxy-3,4,4a,5,6,9,10,11,12,12a-decahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxete-6,12b(2aH)diyl diacetate	155588-13-9	C₃₇H₅₂O₁₀Si	684.899
——	((3aS,8R,9aS,10S,12S,13S,13aR,13bS)-8-acetoxy-13-hydroxy-6,9a,14,14-tetramethyl-12-((methylsulfonyl)oxy)-2,9-dioxo-10-((triethylsilyl)oxy)-5,8,9,9a,10,11,12,13,13a,13b-decahydro-4H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxol-13-yl)methyl acetate	162088-63-3	C₃₂H₅₀O₁₃SSi	702.893
——	((3aS,8R,9aS,10S,12S,13S,13aR,13bS)-8-acetoxy-10,12,13-trihydroxy-6,9a,14,14-tetramethyl-2,9-dioxo-5,8,9,9a,10,11,12,13,13a,13b-decahydro-4H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxol-13-yl)methyl acetate	162088-60-0	C₂₅H₃₄O₁₁	510.538
7-O-(三乙基硅烷基)浆果赤霉素III	7-(triethylsilyl)baccatin III	115437-21-3	C₃₇H₅₂O₁₁Si	700.899
7-三乙基硅烷基-13-氧代浆果赤霉素III	13-oxo-7-O-(triethylsilyl)baccatin III	150665-56-8	C₃₇H₅₀O₁₁Si	698.883
——	[(1S,2S,3R,4S,7R,9S,10S,12R)-1,2,12-trihydroxy-10,14,17,17-tetramethyl-11,15-dioxo-9-triethylsilyloxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-4-yl] acetate	155588-19-5	C₂₈H₄₄O₉Si	552.737
——	[(1S,5S,6R,7S,8S,10S,11S,13R)-13-acetyloxy-7,8-dihydroxy-11,15,18,18-tetramethyl-3,12-dioxo-10-phenylmethoxy-2,4-dioxatetracyclo[12.3.1.01,5.06,11]octadec-14-en-7-yl]methyl acetate	162238-75-7	C₃₂H₄₀O₁₁	600.663
——	[(1S,5S,6R,7S,8S,10S,11S,13R)-7,8-dihydroxy-7-(hydroxymethyl)-11,15,18,18-tetramethyl-3,12-dioxo-10-phenylmethoxy-2,4-dioxatetracyclo[12.3.1.01,5.06,11]octadec-14-en-13-yl] acetate	162238-74-6	C₃₀H₃₈O₁₀	558.626
——	[(1'S,4S,5'S,6'R,8'S,10'S,11'S,13'R)-8'-hydroxy-2,2,11',15',18',18'-hexamethyl-3',12'-dioxo-10'-phenylmethoxyspiro[1,3-dioxolane-4,7'-2,4-dioxatetracyclo[12.3.1.01,5.06,11]octadec-14-ene]-13'-yl] acetate	162088-59-7	C₃₃H₄₂O₁₀	598.69
7-O-(三乙基硅烷基)-10-去乙酰基浆果赤霉素III	7-triethylsilyl-10-deacetylbaccatin III	115437-18-8	C₃₅H₅₀O₁₀Si	658.861
——	[(1'S,4S,5'S,6'R,10'S,11'S,13'R)-2,2,11',15',18',18'-hexamethyl-3',12'-dioxo-10'-phenylmethoxyspiro[1,3-dioxolane-4,7'-2,4-dioxatetracyclo[12.3.1.01,5.06,11]octadeca-8,14-diene]-13'-yl] acetate	162238-72-4	C₃₃H₄₀O₉	580.675
——	7-triethylsilyl-13-dehydro-10-deacetylbaccatin III	155588-21-9	C₃₅H₄₈O₁₀Si	656.846
巴卡丁 III	baccatin III	27548-93-2	C₃₁H₃₈O₁₁	586.636
——	[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-1-hydroxy-15-(imidazole-1-carbothioyloxy)-10,14,17,17-tetramethyl-11-oxo-9-triethylsilyloxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate	155588-18-4	C₄₁H₅₄N₂O₁₁SSi	811.038
10-脱乙酰基巴卡丁 III	10-deacetylbaccatin III	32981-86-5	C₂₉H₃₆O₁₀	544.599
——	[(1'S,4S,5'S,6'R,10'S,11'R,12'S,13'R)-12'-hydroxy-2,2,11',15',18',18'-hexamethyl-3'-oxo-10'-phenylmethoxyspiro[1,3-dioxolane-4,7'-2,4-dioxatetracyclo[12.3.1.01,5.06,11]octadeca-8,14-diene]-13'-yl] acetate	162088-37-1	C₃₃H₄₂O₉	582.691
——	(1'S,4S,5'S,6'R,10'S,11'R,12'S,13'R)-12',13'-dihydroxy-2,2,11',15',18',18'-hexamethyl-10'-phenylmethoxyspiro[1,3-dioxolane-4,7'-2,4-dioxatetracyclo[12.3.1.01,5.06,11]octadeca-8,14-diene]-3'-one	155899-05-1	C₃₁H₄₀O₈	540.654

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	[(1S,5S,6R,7S,10R,12S,13S,15R)-7-hydroxy-13,17,20,20-tetramethyl-3,14-dioxo-12-triethylsilyloxy-2,4,9-trioxapentacyclo[14.3.1.01,5.06,13.07,10]icos-16-en-15-yl] acetate	162238-76-8	C₂₉H₄₄O₉Si	564.748
——	(2S,3a'S,8'R,9a'S,10'S,12'S,13a'R,13b'S)-6',9a',14',14'-tetramethyl-2',9'-dioxo-10'-((triethylsilyl)oxy)-4',5',8',9',9a',10',11',12',13a',13b'-decahydrospiro[oxirane-2,13'-[3a,7]methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxole]-8',12'-diyl diacetate	162088-58-6	C₃₁H₄₆O₁₀Si	606.786
——	(3aS,8R,9aS,10S,12S,13S,13aR,13bS)-13-hydroxy-13-(hydroxymethyl)-6,9a,14,14-tetramethyl-2,9-dioxo-10-((triethylsilyl)oxy)-5,8,9,9a,10,11,12,13,13a,13b-decahydro-4H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxole-8,12-diyl diacetate	162088-56-4	C₃₁H₄₈O₁₁Si	624.801
——	[(1S,5S,6R,7S,8S,10S,11S,13R)-13-acetyloxy-7,8-dihydroxy-11,15,18,18-tetramethyl-3,12-dioxo-10-triethylsilyloxy-2,4-dioxatetracyclo[12.3.1.01,5.06,11]octadec-14-en-7-yl]methyl acetate	162088-55-3	C₃₁H₄₈O₁₁Si	624.801
——	(3aS,8R,9aS,10S,12S,13S,13aR,13bS)-12,13-dihydroxy-6,9a,14,14-tetramethyl-2,9-dioxo-10-((triethylsilyl)oxy)-13-(((trimethylsilyl)oxy)methyl)-5,8,9,9a,10,11,12,13,13a,13b-decahydro-4H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxol-8-yl acetate	162088-61-1	C₃₂H₅₄O₁₀Si₂	654.946
——	(3aS,8R,9aS,10S,12S,13S,13aR,13bS)-13-hydroxy-6,9a,14,14-tetramethyl-13-(((methylsulfonyl)oxy)methyl)-2,9-dioxo-10-((triethylsilyl)oxy)-5,8,9,9a,10,11,12,13,13a,13b-decahydro-4H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxole-8,12-diyl diacetate	162088-57-5	C₃₂H₅₀O₁₃SSi	702.893
——	[(1S,5S,6R,7S,8S,10S,11S,13R)-7-hydroxy-7-(hydroxymethyl)-11,15,18,18-tetramethyl-8-methylsulfonyloxy-3,12-dioxo-10-triethylsilyloxy-2,4-dioxatetracyclo[12.3.1.01,5.06,11]octadec-14-en-13-yl] acetate	162088-64-4	C₃₀H₄₈O₁₂SSi	660.855
——	((3aS,8R,9aS,10S,12S,13S,13aR,13bS)-8-acetoxy-13-hydroxy-6,9a,14,14-tetramethyl-12-((methylsulfonyl)oxy)-2,9-dioxo-10-((triethylsilyl)oxy)-5,8,9,9a,10,11,12,13,13a,13b-decahydro-4H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxol-13-yl)methyl acetate	162088-63-3	C₃₂H₅₀O₁₃SSi	702.893
——	((3aS,8R,9aS,10S,12S,13S,13aR,13bS)-8-acetoxy-10,12,13-trihydroxy-6,9a,14,14-tetramethyl-2,9-dioxo-5,8,9,9a,10,11,12,13,13a,13b-decahydro-4H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxol-13-yl)methyl acetate	162088-60-0	C₂₅H₃₄O₁₁	510.538

反应信息

作为反应物：

描述：

(3aS,8R,9aS,10S,11aR,13aS,13bR,13cS)-6,9a,14,14-tetramethyl-2,9-dioxo-10-triethylsilyloxy-4,5,8,9,9a,10,11,11a,13b,13c-decahydro-3a,7-methanooxeto[2'',3'':5',6']benzo[1',2':3,4]cyclodeca[1,2-d][1,3]dioxole-8,13a(13H)diyl diacetate 在氟化氢吡啶作用下，以四氢呋喃为溶剂，反应 2.0h，以88%的产率得到(3aS,8R,9aS,10S,11aR,13aS,13bR,13cS)-10-hydroxy-6,9a,14,14-tetramethyl-2,9-dioxo-4,5,8,9,9a,10,11,11a,13b,13c-decahydro-3a,7-methanooxeto[2'',3'':5',6']benzo[1',2':3,4]cyclodeca[1,2-d][1,3]dioxole-8,13a(13H)diyl diacetate

参考文献：

名称：

紫杉醇的全合成。1. 逆合成、降解和重组

摘要：

已经开发了一种成功的策略，用于对映选择性合成紫杉醇 (1) 的天然立体异构体。该策略利用了来自环 A (10) 和 C (9) 的预制合成子的紫杉醇中央八元 B 环的会聚组装，随后引入了 D 环和侧链。降解研究证实了某些关键操作的可行性，包括 C13 位置的氧化 (35 3) 和区域选择性引入 C1-羟基、CZ苯甲酰氧基部分 (29 31)。此外，还开发了一种用于大规模生产 29（一种可用于 C2 模拟生产的衍生物）的便捷方法。

DOI：

10.1021/ja00107a006
作为产物：

描述：

10-脱乙酰基巴卡丁 III 在吡啶、 4-二甲氨基吡啶、偶氮二异丁腈、三正丁基氢锡、 potassium carbonate 作用下，以四氢呋喃、甲苯为溶剂，反应 101.25h，生成 (3aS,8R,9aS,10S,11aR,13aS,13bR,13cS)-6,9a,14,14-tetramethyl-2,9-dioxo-10-triethylsilyloxy-4,5,8,9,9a,10,11,11a,13b,13c-decahydro-3a,7-methanooxeto[2'',3'':5',6']benzo[1',2':3,4]cyclodeca[1,2-d][1,3]dioxole-8,13a(13H)diyl diacetate

参考文献：

名称：

紫杉醇的全合成。1. 逆合成、降解和重组

摘要：

已经开发了一种成功的策略，用于对映选择性合成紫杉醇 (1) 的天然立体异构体。该策略利用了来自环 A (10) 和 C (9) 的预制合成子的紫杉醇中央八元 B 环的会聚组装，随后引入了 D 环和侧链。降解研究证实了某些关键操作的可行性，包括 C13 位置的氧化 (35 3) 和区域选择性引入 C1-羟基、CZ苯甲酰氧基部分 (29 31)。此外，还开发了一种用于大规模生产 29（一种可用于 C2 模拟生产的衍生物）的便捷方法。

DOI：

10.1021/ja00107a006

点击查看最新优质反应信息

文献信息

Novel chemistry of taxol. Retrosynthetic and synthetic studies

作者：K. C. Nicolaou、P. G. Nantermet、H. Ueno、R. K. Guy

DOI：10.1039/c39940000295

日期：——

10-Deacetyl baccatin III 2 was used in the synthesis of compounds 4–6 and 11–15, all of which were converted to Taxol 1via efficient synthetic pathways

10-去乙酰基浆果赤霉素III在化合物4至6以及11至15的合成中被使用，这些化合物通过有效的合成途径最终转变为紫杉醇。
Formal Total Synthesis of (−)-Taxol through Pd-Catalyzed Eight-Membered Carbocyclic Ring Formation

作者：Sho Hirai、Masayuki Utsugi、Mitsuhiro Iwamoto、Masahisa Nakada

DOI：10.1002/chem.201404295

日期：2015.1.2

A formal total synthesis of (−)‐taxol by a convergent approach utilizing Pd‐catalyzed intramolecular alkenylation is described. Formation of the eight‐membered carbocyclic ring has been a problem in the convergent total synthesis of taxol but it was solved by the Pd‐catalyzed intramolecular alkenylation of a methyl ketone affording the cyclized product in excellent yield (97 %), indicating the high

描述了通过聚合方法利用钯催化的分子内烯基化的形式正式合成（-）-紫杉醇。八元碳环的形成一直是紫杉醇聚合全合成中的一个问题，但已通过Pd催化的甲基酮分子内烯基化反应得以解决，从而以优异的收率（97％）提供了环化产物，表明该方法具有较高的收率。钯催化的分子内烯基化反应发现环氧苄醚通过1,5-氢化物移位进行重排，生成C3立体异构中心，随后形成C1-C2苄叉，并用于制备Pd催化反应的底物。
Total Synthesis of Taxol. 4. The Final Stages and Completion of the Synthesis

作者：K. C. Nicolaou、H. Ueno、J.-J. Liu、P. G. Nantermet、Z. Yang、J. Renaud、K. Paulvannan、R. Chadha

DOI：10.1021/ja00107a009

日期：1995.1

The total synthesis of (-)-Taxol has been achieved. Functional group manipulation of diol 2 provided the ABC ring system with the correct C9-keto, C10-acetyloxy functionality. Careful optimization allowed the oxidation of the C5-C6 alkene in 4 at C5 via a hydroboration reaction. Functional group manipulation of this product, 29, provided, through two routes, the oxetane D ring as 36. Following the method developed by degradative studies provided the natural enantiomer of Taxol (1).