2'-O-acetyltylosin | 69988-46-1

分子结构分类

有机化合物 - 有机氧化合物

中文名称

——

中文别名

——

英文名称

2'-O-acetyltylosin

英文别名

[(2R,3R,4S,5S,6R)-5-[(2S,4R,5S,6S)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-4-(dimethylamino)-2-[[(4R,5S,6S,7R,9R,11E,13E,15R,16R)-16-ethyl-4-hydroxy-15-[[(2R,3R,4R,5R,6R)-5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl]oxymethyl]-5,9,13-trimethyl-2,10-dioxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-6-yl]oxy]-6-methyloxan-3-yl] acetate

CAS

69988-46-1

化学式

C₄₈H₇₉NO₁₈

mdl

——

分子量

958.151

InChiKey

XFPRNDJLWUNNQQ-BZPRWAPXSA-N

BEILSTEIN

——

EINECS

——

计算性质

辛醇/水分配系数(LogP)：

1.6
重原子数：

67
可旋转键数：

15
环数：

4.0
sp3杂化的碳原子比例：

0.83
拓扑面积：

245
氢给体数：

4
氢受体数：

19

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
泰乐菌素	tylosin	1401-69-0	C₄₆H₇₇NO₁₇	916.114

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	2',4'''-di-O-acetyltylosin	86031-95-0	C₅₀H₈₁NO₁₉	1000.19
——	2',4'',4'''-tri-O-acetyltylosin	84120-91-2	C₅₂H₈₃NO₂₀	1042.23
——	2',4'''-di-O-acetyl-4''-O-isovaleryltylosin	122825-65-4	C₅₅H₈₉NO₂₀	1084.31
——	2',3-di-O-acetyl-4''-O-isovaleryltylosin	105386-38-7	C₅₅H₈₉NO₂₀	1084.31
——	2',3,4'''-tri-O-acetyl-4''-O-isovaleryltylosin	122825-66-5	C₅₇H₉₁NO₂₁	1126.34
——	2',3-di-O-acetyl-23-O-demycinosyl-4''-O-isovaleryltylosin	90577-41-6	C₄₇H₇₅NO₁₆	910.11
泰伐洛星	tylvalosin	63409-12-1	C₅₃H₈₇NO₁₉	1042.27
——	[(2R,3R,4S,5S,6R)-4-(dimethylamino)-2-[[(4R,5S,6S,7R,9R,11E,13E,15R,16R)-16-ethyl-4-hydroxy-15-[[(2R,3R,4R,5R,6R)-5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl]oxymethyl]-5,9,13-trimethyl-2,10-dioxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-6-yl]oxy]-6-methyl-5-prop-2-enoxyoxan-3-yl] acetate	518980-15-9	C₄₄H₇₁NO₁₅	854.045
——	3,23-di-O-acetyl-23-O-demycinosyl-4''-O-isovaleryltylosin	122825-64-3	C₄₇H₇₅NO₁₆	910.11
——	[(2R,3R,4S,5S,6R)-4-(dimethylamino)-2-[[(4R,5S,6S,7R,9R,11E,13E,15R,16R)-7-(1,3-dioxolan-2-ylmethyl)-16-ethyl-4-hydroxy-15-[[(2R,3R,4R,5R,6R)-5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl]oxymethyl]-5,9,13-trimethyl-2,10-dioxo-1-oxacyclohexadeca-11,13-dien-6-yl]oxy]-6-methyl-5-prop-2-enoxyoxan-3-yl] acetate	518980-14-8	C₄₆H₇₅NO₁₆	898.099
——	[(2R,3R,4S,5S,6R)-4-(dimethylamino)-2-[[(4R,5S,6S,7R,9R,11E,13E,15R,16R)-7-(1,3-dioxolan-2-ylmethyl)-16-ethyl-4-hydroxy-15-[[(2R,3R,4R,5R,6R)-5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl]oxymethyl]-5,9,13-trimethyl-2,10-dioxo-1-oxacyclohexadeca-11,13-dien-6-yl]oxy]-5-hydroxy-6-methyloxan-3-yl] acetate	518980-11-5	C₄₃H₇₁NO₁₆	858.034
——	3-deoxy-4''-O-isovaleryl-3,19-cyclotylosin	122825-69-8	C₅₁H₈₃NO₁₇	982.217
——	2',3-di-O-acetyl-4'''-deoxy-4''-O-isovaleryl-4'''-oxotylosin	122825-72-3	C₅₅H₈₇NO₂₀	1082.29
——	[(2S,3S,4R,6S)-6-[(2R,3S,4R,5R,6R)-4-(dimethylamino)-6-[[(4R,5S,6S,7R,9R,11E,13E,15R,16R)-16-ethyl-4-hydroxy-15-[[(2R,3R,4R,5R,6R)-5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl]oxymethyl]-5,9,13-trimethyl-2,10-dioxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-6-yl]oxy]-5-hydroxy-2-methyloxan-3-yl]oxy-4-hydroxy-2,4-dimethyloxan-3-yl] N,N-diethylcarbamate	——	C₅₁H₈₆N₂O₁₈	1015.25
——	2',3-di-O-acetyl-23-O-demycinosyl-4''-O-isovaleryl-23-O-phenylacetyltylosin	122825-62-1	C₅₅H₈₁NO₁₇	1028.24
——	4"-O-benzyltylosin	114442-69-2	C₅₃H₈₃NO₁₇	1006.24
——	3-O-acetyl-23-O-demycinosyl-4''-O-isovaleryl-23-O-phenylacetyltylosin	122825-63-2	C₅₃H₇₉NO₁₆	986.207
——	4"-O-(4-methoxyphenyl)acetyltylosin	103360-00-5	C₅₅H₈₅NO₁₉	1064.28
——	ABBV-4083	1809266-03-2	C₅₃H₈₂FNO₁₇	1024.23
——	[(2R,3R,4S,5S,6R)-4-(dimethylamino)-2-[[(4R,5S,6S,7R,9R,11E,13E,15R,16R)-16-ethyl-4-hydroxy-15-[[(2R,3R,4R,5R,6R)-5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl]oxymethyl]-5,9,13-trimethyl-2,10-dioxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-6-yl]oxy]-6-methyl-5-(2-phenylethylcarbamoyloxy)oxan-3-yl] acetate	1054614-15-1	C₅₀H₇₆N₂O₁₆	961.157
——	[(2R,3R,4S,5S,6R)-4-(dimethylamino)-2-[[(4R,5S,6S,7R,9R,11E,13E,15R,16R)-7-(1,3-dioxolan-2-ylmethyl)-16-ethyl-4-hydroxy-15-[[(2R,3R,4R,5R,6R)-5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl]oxymethyl]-5,9,13-trimethyl-2,10-dioxo-1-oxacyclohexadeca-11,13-dien-6-yl]oxy]-6-methyl-5-(2-phenylethylcarbamoyloxy)oxan-3-yl] acetate	700377-64-6	C₅₂H₈₀N₂O₁₇	1005.21
——	2',3-di-O-acetyl-23-O-demycinosyl-20-deoxo-20-<(4,4-dioxothiomorpholino)imino>-4''-O-isovaleryltylosin	122825-74-5	C₅₁H₈₃N₃O₁₇S	1042.3
——	2',3-di-O-acetyl-2''',3'''-didehydro-2'''-demethoxy-4'''-deoxy-4''-O-isovaleryl-4'''-oxotylosin	122825-73-4	C₅₄H₈₃NO₁₉	1050.25
——	3-O-acetyl-23-O-demycinosyl-20-deoxo-20-<(4,4-dioxothiomorpholino)imino>-4''-O-isovaleryltylosin	122825-75-6	C₄₉H₈₁N₃O₁₆S	1000.26
——	2'-O-acetyl-3",4"-O-(dibutylstannio)tylosin	114442-75-0	C₅₆H₉₅NO₁₈Sn	1189.08
——	[(2R,3R,4S,5S,6R)-4-(dimethylamino)-2-[[(4R,5S,6S,7R,9R,11E,13E,15R,16R)-16-ethyl-4-hydroxy-15-[[(2R,3R,4R,5R,6R)-5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl]oxymethyl]-5,9,13-trimethyl-2,10-dioxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-6-yl]oxy]-6-methyl-5-[(Z)-3-quinolin-3-ylprop-1-enoxy]oxan-3-yl] acetate	731785-14-1	C₅₃H₇₆N₂O₁₅	981.191
——	[(2R,3R,4S,5S,6R)-2-[[(4R,5S,6S,7R,9R,11E,13E,15R,16R)-15-[[(2R,3R,4S,5R,6R)-5-[tert-butyl(diphenyl)silyl]oxy-3,4-dimethoxy-6-methyloxan-2-yl]oxymethyl]-7-(1,3-dioxolan-2-ylmethyl)-16-ethyl-4-hydroxy-5,9,13-trimethyl-2,10-dioxo-1-oxacyclohexadeca-11,13-dien-6-yl]oxy]-4-(dimethylamino)-6-methyl-5-prop-2-enoxyoxan-3-yl] acetate	518980-13-7	C₆₂H₉₃NO₁₆Si	1136.5
——	[(2R,3R,4S,5S,6R)-2-[[(4R,5S,6S,7R,9R,11E,13E,15R,16R)-15-[[(2R,3R,4S,5R,6R)-5-[tert-butyl(diphenyl)silyl]oxy-3,4-dimethoxy-6-methyloxan-2-yl]oxymethyl]-7-(1,3-dioxolan-2-ylmethyl)-16-ethyl-4-hydroxy-5,9,13-trimethyl-2,10-dioxo-1-oxacyclohexadeca-11,13-dien-6-yl]oxy]-4-(dimethylamino)-5-hydroxy-6-methyloxan-3-yl] acetate	518980-12-6	C₅₉H₈₉NO₁₆Si	1096.44
——	[(2R,3R,4S,5S,6R)-2-[[(4R,5S,6S,7R,9R,11E,13E,15R,16R)-15-[[(2R,3R,4S,5R,6R)-5-[tert-butyl(diphenyl)silyl]oxy-3,4-dimethoxy-6-methyloxan-2-yl]oxymethyl]-7-(1,3-dioxolan-2-ylmethyl)-16-ethyl-4-hydroxy-5,9,13-trimethyl-2,10-dioxo-1-oxacyclohexadeca-11,13-dien-6-yl]oxy]-4-(dimethylamino)-6-methyl-5-(2-phenylethylcarbamoyloxy)oxan-3-yl] acetate	700377-66-8	C₆₈H₉₈N₂O₁₇Si	1243.61

反应信息

作为反应物：

描述：

2'-O-acetyltylosin 在咪唑、盐酸、甲醇、 tris-(dibenzylideneacetone)dipalladium(0) 、四丁基氟化铵、对甲苯磺酸、 1,4-双(二苯基膦)丁烷、乙腈作用下，以四氢呋喃、 N,N-二甲基甲酰胺、乙腈、苯为溶剂，反应 58.0h，生成 2-[(4R,5S,6S,7R,9R,11E,13E,15R,16R)-6-[(2R,3R,4R,5S,6R)-4-(dimethylamino)-3-hydroxy-6-methyl-5-prop-2-enoxyoxan-2-yl]oxy-16-ethyl-4-hydroxy-15-[[(2R,3R,4R,5R,6R)-5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl]oxymethyl]-5,9,13-trimethyl-2,10-dioxo-1-oxacyclohexadeca-11,13-dien-7-yl]acetaldehyde

参考文献：

名称：

泰乐菌素衍生的新型4'-取代的16元环大环内酯类化合物的合成和抗菌活性。

摘要：

通过裂解泰乐菌素的麦芽糖并随后修饰4'-羟基合成了新颖的4'-取代的16元环大环内酯。这类新的大环内酯类抗生素对某些关键的抗红霉素病原体表现出有效的活性。

DOI：

10.1021/jm034233n
作为产物：

描述：

乙酸酐、 tylosin tartrate 以乙醇为溶剂，反应 4.0h，生成 2'-O-acetyltylosin

参考文献：

名称：

TYLOSIN A ANALOGS AND DERIVATIVES

摘要：

本发明涉及霉素A的衍生物。具体而言，本发明涉及具有式（I）结构的化合物。本发明还涉及包含霉素A衍生物的组合物以及使用这些化合物和组合物治疗或预防疾病或疾病的方法。

公开号：

US20150259374A1

点击查看最新优质反应信息

文献信息

Semisynthetic macrolide antibacterials derived from tylosin. Synthesis of 3-O-acetyl-23-O-demycinosyl-4″-O-isovaleryltylosin and related compounds, as well as the 12,13-epoxy derivatives

作者：Andrew G. Fishman、Alan K. Mallams、Randall R. Rossman

DOI：10.1039/p19890000787

日期：——

syntheses of the 2′-O-acetyl, 23-O-acetyl, and 2′,23-di-O-acetyl derivatives of the latter are also described. The synthesis of key hydrazones is also described. The regio- and stereo-selective epoxidation of tylosin and its acyl derivatives afforded the 12,13-epoxy analogues, which were used to synthesize novel acylated 12,13-epoxy derivatives of 23-O-demycinosyltylosin.

已经开发出选择性的酰化技术，其使得能够以有效的方式合成3 - O-乙酰基-4” -O-异戊基酪氨醇和3 - O-乙酰基-23- O-去甲霉素-4” -O-异戊基酪氨素。从泰乐菌素开始。还描述了后者的2'- O-乙酰基，23- O-乙酰基和2'，23-二-O-乙酰基衍生物的合成。还描述了关键的合成。泰乐菌素及其酰基衍生物的区域和立体选择性环氧化提供了12,13-环氧类似物，其被用于合成新型的23- O-脱mycinosyltylosin的酰化的12,13-环氧衍生物。
Application of dibutyltin oxide method to regioselective acylation and alkylation of tylosin at C-4".

作者：Kohki KIYOSHIMA、Michiko SAKAMOTO、Tomoyuki ISHIKURA、Yasuo FUKAGAWA、Takeo YOSHIOKA、Hiroshi NAGANAWA、Tsutomu SAWA、Tomio TAKEUCHI

DOI：10.1248/cpb.37.861

日期：——

4"-O-Acyl-, 4"-O-alkyl- and 4"-deoxy-tylosin derivatives were synthesized using 2'-O-acetyl-3", 4"-O-(dibutyl-stannio)tylosin as a synthetic intermediate. The in vitro biological evaluation showed that the new derivatives were active against macrolide-resistant clinical isolates of bacteria and mycoplasmas, and that they were resistant to hepatic esterase.

以2'-O-乙酰基-3"、4"-O-(二丁基锡)泰乐菌素为合成中间体，合成了4"-O-酰基、4"-O-烷基和4"-脱氧泰乐菌素衍生物。体外生物学评估表明，新衍生物对临床分离的大环内酯类耐药细菌和支原体具有活性，并且对肝酯酶具有抗性。
Treatment of filarial diseases

申请人：AbbVie Inc.

公开号：US10238677B2

公开（公告）日：2019-03-26

The present invention pertains to prevention of and/or treatment for filariasis. In particular, the present invention pertains to the use of tylosin A and its analogs and derivatives to prevent or treat filarial worm infection and/or diseases associated with filarial worm infection. The present invention also pertains to pharmaceutical compositions comprising tylosin A or an analog or derivative thereof for use in preventing or treating filarial worm infection and/or diseases associated with filarial worm infection.

本发明涉及丝虫病的预防和/或治疗。特别是，本发明涉及使用泰乐菌素 A 及其类似物和衍生物来预防或治疗丝虫感染和/或与丝虫感染相关的疾病。本发明还涉及包含泰乐菌素A或其类似物或衍生物的药物组合物，用于预防或治疗丝虫感染和/或与丝虫感染相关的疾病。
JOSIOKA, TAKEHO;KIESIMA, KOKI;XASEHBEH, YUKIKO;FUKAVA, YASUO;ISIKURA, TOM+

作者：JOSIOKA, TAKEHO、KIESIMA, KOKI、XASEHBEH, YUKIKO、FUKAVA, YASUO、ISIKURA, TOM+

DOI：——

日期：——
KIESIMA, KOKI;YAMAMOTO, RIO;MORI, TOSIO

作者：KIESIMA, KOKI、YAMAMOTO, RIO、MORI, TOSIO

DOI：——

日期：——

2'-O-acetyltylosin | 69988-46-1

分子结构分类

计算性质

上下游信息

反应信息

文献信息

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