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

(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

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

(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

英文别名

13-deoxy-7-O-(triethylsilyl)baccatin III；13-deoxy-7-O-TES-baccatin III；[(1S,2S,3R,4S,7R,9S,10S,12R)-4,12-diacetyloxy-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9-triethylsilyloxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate

(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化学式

CAS

155588-13-9

化学式

C₃₇H₅₂O₁₀Si

mdl

——

分子量

684.899

InChiKey

SYIWZHVVLBWQRU-OZARNXOVSA-N

BEILSTEIN

——

EINECS

——

物化性质

沸点：

691.1±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)：

5.71
重原子数：

48
可旋转键数：

12
环数：

5.0
sp3杂化的碳原子比例：

0.68
拓扑面积：

135
氢给体数：

1
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
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
——	(2aR,4S,4aS,6R,11S,12S,12aR,12bS)-12b-acetoxy-6,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-4-((triethylsilyl)oxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-12-yl benzoate	168421-82-7	C₃₅H₅₀O₉Si	642.862
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
——	13-deoxybaccatin III	155588-14-0	C₃₁H₃₈O₁₀	570.637
——	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
——	[(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
——	[(1S,2S,3R,4S,7R,9S,10S)-4-acetyloxy-1-hydroxy-10,14,17,17-tetramethyl-12-oxo-9-triethylsilyloxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate	168421-81-6	C₃₅H₅₀O₈Si	626.863
——	[(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,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
——	(1aS,3aS,4S,5aR,7aS,7bR,8S,9S,11aR)-7a-acetoxy-9-hydroxy-3a,11a,12,12-tetramethyl-2-methylene-4-((triethylsilyl)oxy)tetradecahydro-1a,9-methanooxireno[2'',3'':5',6']cyclodeca[1',2':3,4]benzo[1,2-b]oxet-8-yl benzoate	168421-79-2	C₃₆H₅₂O₈Si	640.89
——	[(1S,4S,5S,7R,10S,11R,12S,13S,16R)-10-acetyloxy-13-hydroxy-4,16,18,18-tetramethyl-2-oxo-5-triethylsilyloxy-8,17-dioxapentacyclo[11.4.1.01,16.04,11.07,10]octadecan-12-yl] benzoate	168421-80-5	C₃₅H₅₀O₉Si	642.862
——	(4S,5S)-4-[(1S,2R,3S,4S,6R)-1-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3-(2,2-dimethoxy-ethyl)-3-methyl-7-oxa-bicyclo[4.2.0]oct-2-yl]-6,6,8-trimethyl-1,3-dioxa-spiro[4.5]dec-8-ene-2,7-dione	168421-68-9	C₃₆H₅₄O₉Si	658.905
——	(1S,5S,6R,7S,10R,12S,13S)-13,17,20,20-tetramethyl-15-methylidene-7-phenylmethoxy-12-triethylsilyloxy-2,4,9-trioxapentacyclo[14.3.1.01,5.06,13.07,10]icos-16-en-3-one	168421-75-8	C₃₅H₅₀O₆Si	594.864
——	(1S,6S)-1-{(S)-[(1S,2R,3S,4S,6R)-1-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3-(2,2-dimethoxy-ethyl)-3-methyl-7-oxa-bicyclo[4.2.0]oct-2-yl]-hydroxy-methyl}-2,2,4-trimethyl-7-oxa-bicyclo[4.1.0]hept-4-en-3-one	168421-66-7	C₃₅H₅₄O₈Si	630.894
——	(1S,5S,6R,7S,10R,12S,13S)-12-[tert-butyl(dimethyl)silyl]oxy-13,17,20,20-tetramethyl-15-methylidene-7-phenylmethoxy-2,4,9-trioxapentacyclo[14.3.1.01,5.06,13.07,10]icos-16-en-3-one	168421-73-6	C₃₅H₅₀O₆Si	594.864
——	(1S,4S,5S,7R,10S,11R,12S,16S,19R)-4,19,21,21-tetramethyl-2-methylidene-10-phenylmethoxy-5-triethylsilyloxy-8,13,15,20-tetraoxahexacyclo[14.4.1.01,19.04,11.07,10.012,16]henicosan-14-one	168421-76-9	C₃₅H₅₀O₇Si	610.863
——	(S)-5-{(S)-[(1S,2R,3S,4S,6R)-1-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3-(2,2-dimethoxy-ethyl)-3-methyl-7-oxa-bicyclo[4.2.0]oct-2-yl]-hydroxy-methyl}-5-hydroxy-2,6,6-trimethyl-cyclohex-2-enone	168421-67-8	C₃₅H₅₆O₈Si	632.91
——	5-[(S)-[(1S,2R,3S,4S,6R)-4-[tert-butyl(dimethyl)silyl]oxy-3-(2,2-dimethoxyethyl)-3-methyl-1-phenylmethoxy-7-oxabicyclo[4.2.0]octan-2-yl]-hydroxymethyl]-2,6,6-trimethylcyclohexa-2,4-dien-1-one	168421-65-6	C₃₅H₅₄O₇Si	614.895
——	[(4S,5S)-4-[(1S,2R,3S,4S,6R)-4-[tert-butyl(dimethyl)silyl]oxy-3-methyl-3-(2-oxoethyl)-1-phenylmethoxy-7-oxabicyclo[4.2.0]octan-2-yl]-6,6,8-trimethyl-2-oxo-1,3-dioxaspiro[4.5]dec-7-en-7-yl] trifluoromethanesulfonate	168421-71-4	C₃₅H₄₉F₃O₁₀SSi	746.915
——	Trifluoro-methanesulfonic acid (4S,5S)-4-[(1S,2R,3S,4S,6R)-1-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3-(2,2-dimethoxy-ethyl)-3-methyl-7-oxa-bicyclo[4.2.0]oct-2-yl]-6,6,8-trimethyl-2-oxo-1,3-dioxa-spiro[4.5]dec-7-en-7-yl ester	168421-70-3	C₃₇H₅₅F₃O₁₁SSi	792.984
——	[(4S,5S)-4-[(1S,2R,3S,4S,6R)-4-[tert-butyl(dimethyl)silyl]oxy-3-methyl-1-phenylmethoxy-3-prop-2-enyl-7-oxabicyclo[4.2.0]octan-2-yl]-6,6,8-trimethyl-2-oxo-1,3-dioxaspiro[4.5]dec-7-en-7-yl] trifluoromethanesulfonate	168421-72-5	C₃₆H₅₁F₃O₉SSi	744.942
——	(4S,5S)-4-[(1S,2R,3S,4S,6R)-4-[tert-butyl(dimethyl)silyl]oxy-3-(2,2-dimethoxyethyl)-3-methyl-1-phenylmethoxy-7-oxabicyclo[4.2.0]octan-2-yl]-6,6,8-trimethyl-1,3-dioxaspiro[4.5]decane-2,7-dione	168421-69-0	C₃₆H₅₆O₉Si	660.921
——	(3aS,9aS,10S,11aR,13aS,13bR,13cS)-13a-(benzyloxy)-10-hydroxy-6,9a,14,14-tetramethyl-8-methylene-4,5,8,9,9a,10,11,11a,13,13a,13b,13c-dodecahydro-3a,7-methanooxeto[2'',3'':5',6']benzo[1',2':3,4]cyclodeca[1,2-d][1,3]dioxol-2-one	168421-74-7	C₂₉H₃₆O₆	480.601
——	(1aS,3aS,4S,5aR,7aS,7bR,7cS,10aS,12aR)-3a,12a,13,13-tetramethyl-2-methylene-9-oxo-4-((triethylsilyl)oxy)decahydro-11H-1a,10a-methanooxeto[2'',3'':5',6']benzo[1',2':3,4]oxireno[2',3':7,8]cyclodeca[1,2-d][1,3]dioxol-7a(7H)-yl acetate	168421-78-1	C₃₀H₄₆O₈Si	562.776
——	(1S,4S,5S,7R,10S,11R,12S,16S,19R)-10-hydroxy-4,19,21,21-tetramethyl-2-methylidene-5-triethylsilyloxy-8,13,15,20-tetraoxahexacyclo[14.4.1.01,19.04,11.07,10.012,16]henicosan-14-one	168421-77-0	C₂₈H₄₄O₇Si	520.739
——	(2aR,4S,4aS,6R,8aS,8bS)-8b-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-4a-methyl-octahydro-2-oxa-cyclobuta[a]naphthalen-7-one	174589-62-9	C₂₅H₃₈O₅Si	446.659
——	[(1S,2S,3S,4S,6R)-1-Benzyloxy-3-(2,2-dimethoxy-ethyl)-3-methyl-2-vinyl-7-oxa-bicyclo[4.2.0]oct-4-yloxy]-tert-butyl-dimethyl-silane	168421-62-3	C₂₇H₄₄O₅Si	476.729
——	(1S,2S,3S,4S,6R)-1-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-3-(2,2-dimethoxyethyl)-3-methyl-7-oxabicyclo[4.2.0]octane-2-carbaldehyde	168421-63-4	C₂₆H₄₂O₆Si	478.701
——	(2aR,4S,4aS,8aS,8bS)-4-[tert-butyl(dimethyl)silyl]oxy-4a-methyl-8b-phenylmethoxy-1,2a,3,4,5,6,8,8a-octahydronaphtho[2,1-b]oxet-7-one	168421-83-8	C₂₅H₃₈O₄Si	430.66
——	[(1S,2S,3S,4S,6R)-1-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-3-(2-oxo-ethyl)-7-oxa-bicyclo[4.2.0]oct-2-yl]-acetic acid methyl ester	174474-74-9	C₂₆H₄₀O₆Si	476.686
——	[(1S,2S,3S,4S,6R)-1-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3-(2,2-dimethoxy-ethyl)-3-methyl-7-oxa-bicyclo[4.2.0]oct-2-yl]-acetic acid methyl ester	168421-60-1	C₂₈H₄₆O₇Si	522.755
——	{(1S,2S,3S,4S,6R)-1-Benzyloxy-3-(2,2-dimethoxy-ethyl)-3-methyl-2-[2-(2-nitro-phenylselanyl)-ethyl]-7-oxa-bicyclo[4.2.0]oct-4-yloxy}-tert-butyl-dimethyl-silane	168421-61-2	C₃₃H₄₉NO₇SeSi	678.8
——	(((2aR,4S,4aS,8aS,8bS)-8b-(benzyloxy)-4a-methyldecahydrospiro[naphtho[2,1-b]oxete-7,2'-[1,3]dioxolan]-4-yl)oxy)(tert-butyl)dimethylsilane	168421-57-6	C₂₇H₄₂O₅Si	474.713
——	2-[(1S,2S,3S,4S,6R)-1-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3-(2,2-dimethoxy-ethyl)-3-methyl-7-oxa-bicyclo[4.2.0]oct-2-yl]-ethanol	168421-84-9	C₂₇H₄₆O₆Si	494.744

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	13-epi-7-O-(triethylsilyl)baccatin III	474766-89-7	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
——	(13R)-13-deoxy-13-tert-butylperoxy-7-O-(triethylsilyl)baccatin III	474766-88-6	C₄₁H₆₀O₁₂Si	773.006
——	13-deoxybaccatin III	155588-14-0	C₃₁H₃₈O₁₀	570.637
——	13β-bromo-13-deoxy-7-O-(triethylsilyl)baccatin III	474766-87-5	C₃₇H₅₁BrO₁₀Si	763.795
——	(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
——	(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	C₃₁H₄₆O₁₀Si	606.786

反应信息

作为反应物：

描述：

(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 在 Celite 、 sodium acetate 、 pyridinium chlorochromate 作用下，以苯为溶剂，以75%的产率得到7-三乙基硅烷基-13-氧代浆果赤霉素III

参考文献：

名称：

Novel chemistry of taxol. Retrosynthetic and synthetic studies

摘要：

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。

DOI：

10.1039/c39940000295
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、 sodium tetrahydroborate 、四丙基高钌酸铵、偶氮二异丁腈、 4 A molecular sieve 、三正丁基氢锡、 potassium carbonate 作用下，以四氢呋喃、甲醇、二氯甲烷、环己烷、甲苯为溶剂，反应 59.0h，生成 (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

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

Total Synthesis of Baccatin III and Taxol

作者：Samuel J. Danishefsky、John J. Masters、Wendy B. Young、J. T. Link、Lawrence B. Snyder、Thomas V. Magee、David K. Jung、Richard C. A. Isaacs、William G. Bornmann、Cheryl A. Alaimo、Craig A. Coburn、Martin J. Di Grandi

DOI：10.1021/ja952692a

日期：1996.1.1

An intramolecular Heck reaction (90 → 91) serves as the key step in the total synthesis of the titled compounds. The synthetic route is based on utilizing the Wieland−Miescher ketone (5) as a matrix to provide the C and D rings of the targets and to provide functionality implements for joining this sector to an A ring precursor (6). Catalytically induced enantiotopic control and early emplacement of

分子内 Heck 反应 (90 → 91) 是标题化合物全合成的关键步骤。合成路线基于利用 Wieland-Miescher 酮 (5) 作为基质来提供目标的 C 和 D 环，并提供将该部分连接到 A 环前体 (6) 的功能性工具。催化诱导的对映体控制和氧杂环丁烷的早期置换是该路线的其他特征。
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。
Masters, John J.; Link, J. T.; Snyder, Lawrence B., Angewandte Chemie, 1995, vol. 107, # 16, p. 1886 - 1888

作者：Masters, John J.、Link, J. T.、Snyder, Lawrence B.、Young, Wendy B.、Danishefsky, Samuel J.

DOI：——

日期：——
Synthetic Studies with 13-Deoxybaccatin III

作者：Yu Mi Ahn、David G. Vander Velde、Gunda I. Georg

DOI：10.1021/jo011183q

日期：2002.10.1

An efficient synthesis of 13-epi-7-O-(triethylsilyl)baccatin III from 13-deoxybaccatin III is described. Oxidation of 13-deoxy-7-O-(triethylsilyl)baccatin III with tert-butyl peroxide, followed by reduction with SmI2, produced 13-epi-7-O-(triethylsilyl)baccatin III in good overall yield. The preparation of 13-oxo-7-O-(triethylsilyl)baccatin III from 13-epi-7-O-(triethylsilyl)baccatin III using tetrapropylammonium perruthenate and N-methylmorpholine N-oxide is also reported.