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(22R,23R,24S)-3β,22,23-triacetoxyergost-5-ene | 90095-32-2

分子结构分类

有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物

中文名称

——

中文别名

——

英文名称

(22R,23R,24S)-3β,22,23-triacetoxyergost-5-ene

英文别名

(22r,23r,24s)-3 b,22,23-Triacetoxy-24-methyl-cholest-5-ene；[(3S,8S,9S,10R,13S,14S,17R)-17-[(2S,3R,4R,5S)-3,4-diacetyloxy-5,6-dimethylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate

(22R,23R,24S)-3β,22,23-triacetoxyergost-5-ene化学式

CAS

90095-32-2

化学式

C₃₄H₅₄O₆

mdl

——

分子量

558.799

InChiKey

JHNYAKRAQAUGBQ-VPESLMFVSA-N

BEILSTEIN

——

EINECS

——

物化性质

沸点：

593.2±30.0 °C(Predicted)
密度：

1.08±0.1 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

8.2
重原子数：

40
可旋转键数：

11
环数：

4.0
sp3杂化的碳原子比例：

0.85
拓扑面积：

78.9
氢给体数：

0
氢受体数：

6

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
——	(22R,23R,24S)-3β-acetoxyergost-5-ene-22,23-diol 22,23-acetonide	83066-66-4	C₃₃H₅₄O₄	514.789
——	(22R,23R,24R)-23,24-epoxy-3β-tetrahydropyranyloxycholest-5-en-22-ol acetate	76976-84-6	C₃₄H₅₄O₅	542.8
——	(22R,23R,24S)-3β-acetoxyergost-5-ene-22,23,28-triol 22,23-acetonide	90095-30-0	C₃₃H₅₄O₅	530.789
——	(3S,8S,9S,10R,13S,14S,17R)-17-((S)-1-((4R,5R)-2,2-dimethyl-5-((S)-3-methyl-1-oxobutan-2-yl)-1,3-dioxolan-4-yl)ethyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate	83066-62-0	C₃₃H₅₂O₅	528.773
——	(22R,23R,24S)-3β-acetoxy-28-iodoergost-5-ene-22,23-diol 22,23-acetonide	83066-65-3	C₃₃H₅₃IO₄	640.686
——	(22R,23R,24S)-24-formylcholest-5-ene-3β,22,23-triol 22,23-acetonide	83066-61-9	C₃₁H₅₀O₄	486.736
——	(22R,23R,24R)-23,24-epoxy-3β-tetrahydropyranyloxycholest-5-en-22-ol	76976-77-7	C₃₂H₅₂O₄	500.762
——	(22R,23R,24S)-24-cyanocholest-5-ene-3β,22,23-triol 22,23-acetonide	83066-60-8	C₃₁H₄₉NO₃	483.735
——	(3S,8S,9S,10R,13S,14S,17R)-17-((S)-1-((4R,5R)-2,2-dimethyl-5-((R)-3-methyl-1-((methylsulfonyl)oxy)butan-2-yl)-1,3-dioxolan-4-yl)ethyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate	90095-31-1	C₃₄H₅₆O₇S	608.88
——	<22S,23(24)Z>-3β-tetrahydropyranyloxycholest-5,23-dien-22-ol	76976-76-6	C₃₂H₅₂O₃	484.763
——	3β-(tetrahydropyran-2-yloxy)-23,24-dinorchol-5-en-22-al	22145-61-5	C₂₇H₄₂O₃	414.629
——	(22S)-3β-tetrahydropyranyloxycholest-5-en-23-yn-22-ol	76976-83-5	C₃₂H₅₀O₃	482.747
——	(22R)-3β-tetrahydropyranyloxycholest-5-en-23-yn-22-ol	76976-75-5	C₃₂H₅₀O₃	482.747
——	(2R,3R,4R,5S)-3,4-dihydroxy-5-((3S,8S,9S,10R,13S,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-isopropylhexanenitrile	83066-59-5	C₂₈H₄₅NO₃	443.67
——	Acetic acid (1R,2R,3S)-2-hydroxy-1-[(S)-1-((3S,5S,6R,8S,9S,10R,13S,14S,17R)-3-hydroxy-6-methoxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-ethyl]-3,4-dimethyl-pentyl ester	104336-47-2	C₃₁H₅₄O₅	506.767
——	(22R,23R,24S)-22,23-diacetoxy-6β-methoxy-24-methyl-3α,5-cyclo-5α-cholestane	431948-58-2	C₃₃H₅₄O₅	530.789
——	Acetic acid (1R,2R,3S)-1-[(S)-1-((1aR,3aR,3bS,5aS,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-ethyl]-2-methoxymethoxy-3,4-dimethyl-pentyl ester	104336-46-1	C₃₃H₅₆O₅	532.805

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	6-deoxoteasterone	85707-12-6	C₂₈H₄₈O₃	432.687

反应信息

作为反应物：

描述：

(22R,23R,24S)-3β,22,23-triacetoxyergost-5-ene 在硼烷、 sodium hydroxide 、双氧水、氢氧化钾作用下，以四氢呋喃、甲醇为溶剂，反应 13.5h，以43%的产率得到(22R,23R,24S)-24-methyl-5α-cholestane-3β,6α,22,23-tetraol

参考文献：

名称：

摘要：

A biosynthetic precursor of brassinolide, (22R,23R,24S)-24-methyl-3alpha-cholestane-3beta,6alpha,22,23-tetraol was synthesized from Delta(23)-22-keto steroid which was obtained from the corresponding 20-carbonitrile oxide. The side chain was built up by a series of successive transformations: hydride reduction of the initial enone, epoxidation of the allyl-like alcohol, and copper(I) cyanide-catalyzed opening of the 23,24-epoxy ring. The cyclic fragment was completed by opening of the cyclopropane ring with subsequent hydroboration and oxidation of the Delta(5)-bond.

DOI：

10.1023/a:1013804119279
作为产物：

描述：

(20S)-3α,5-cyclo-20-formyl-6β-methoxy-5α-pregnane 在 4-二甲氨基吡啶、 Rh/Al₂O₃ 吡啶、 lithium aluminium tetrahydride 、氯化亚砜、氢气、 potassium carbonate 、对甲苯磺酸、 1,8-二氮杂双环[5.4.0]十一碳-7-烯、三乙胺、 lithium diisopropyl amide 作用下，以四氢呋喃、 1,4-二氧六环、乙醚、二氯甲烷、水、乙酸乙酯、苯为溶剂， -78.0~100.0 ℃ 、709.27 kPa 条件下，反应 45.76h，生成 (22R,23R,24S)-3β,22,23-triacetoxyergost-5-ene

参考文献：

名称：

One-step stereochemical determination of four contiguous acyclic chiral centers on a steroidal side chain: a novel synthesis of brassinolide

摘要：

DOI：

10.1021/ja00282a034

点击查看最新优质反应信息

文献信息

Stereoselective synthesis of plant growth-prompting steroids, brassinolide, castasterone, typhasterol, and their 28-nor analogues

作者：Suguru Takatsuto、Naoto Yazawa、Masaji Ishiguro、Masuo Morisaki、Nobuo Ikekawa

DOI：10.1039/p19840000139

日期：——

Plant growth-promoting steroids, brassinolide (1a), (22R,23R,24S)-2α,3α,22,23-tetrahydroxy-B-homo-7-oxa-5α-ergostan-6-one, castasterone (2a), (22R,23R,24S)-2α,3α,22,23-tetrahydroxy-5α-ergo-stan-6-one, 28-norbrassinolide (1b), (22R,23R)-2α,3α,22,23-tetrahydroxy-B-homo-7-oxa-5α-chole-stan-6-one, brassinone (2b), (22R,23R)-2α,3α,22,23-tetrahydroxy-5α-cholestan-6-one, and typh-asterol (2c), (22R,23R,24S)-3α

促进植物生长的类固醇，油菜素内酯（1a），（22 R，23 R，24 S）-2α，3α，22,23-四羟基-B -homo-7-oxa-5α-ergostan-6-one，卡司他酮（ 2a），（22 R，23 R，24 S）-2α，3α，22,23-四羟基-5α-麦角甾烷-6-一，28-去甲油菜素内酯（1b），（22 R，23 R）-2α ，3α，22,23-tetrahydroxy- B -homo-7-oxa-5α-hole-stan-6-，brasinone（2b），（22 R，23 R）-2α，3α，22,23-tetrahydroxy- 5α-胆甾醇-6-1和伤寒甾醇（2c），（22 R，23 R，24 S）-3α，22,23-三羟基-5α.-麦角甾醇-6-，已被立体选择性地合成。这些类固醇在三种不同的生物测定法中显示出非常强的生物学活性。