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(1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-3-(formylmethyl)-1,4-bis-O-(triethylsilyl)cyclopentane-1,4-diol | 213777-19-6

分子结构分类

有机化合物 - 有机金属化合物 - 有机类金属化合物

中文名称

——

中文别名

——

英文名称

(1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-3-(formylmethyl)-1,4-bis-O-(triethylsilyl)cyclopentane-1,4-diol

英文别名

(1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-3-formylmethyl-1,4-di-O-(triethylsilyl)cyclopentane-1,4-diol；2-[(1R,2R,3S,5R)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-3,5-bis(triethylsilyloxy)cyclopentyl]acetaldehyde

(1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-3-(formylmethyl)-1,4-bis-O-(triethylsilyl)cyclopentane-1,4-diol化学式

CAS

213777-19-6

化学式

C₃₆H₆₀O₄Si₃

mdl

——

分子量

641.126

InChiKey

TWJRRUKOPZIKKO-AXXKPAGNSA-N

BEILSTEIN

——

EINECS

——

物化性质

沸点：

596.5±48.0 °C(Predicted)
密度：

0.99±0.1 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

8.57
重原子数：

43
可旋转键数：

18
环数：

3.0
sp3杂化的碳原子比例：

0.64
拓扑面积：

44.8
氢给体数：

0
氢受体数：

4

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,2S,3R,4R)-1,4-Bis(triethylsilyloxy)-3-(methoxycarbonylmethyl)-2-tert-butyldiphenylsilyloxymethylcyclopentane	213777-18-5	C₃₇H₆₂O₅Si₃	671.153

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	tert-butyl-[[(1R,2R,3R,5S)-2-[(Z)-oct-2-enyl]-3,5-bis(triethylsilyloxy)cyclopentyl]methoxy]-diphenylsilane	377078-52-9	C₄₂H₇₂O₃Si₃	709.288
——	[(1R,2R,3R,5S)-3,5-bis(triethylsilyloxy)-2-[(2Z,5Z,8Z)-undeca-2,5,8-trienyl]cyclopentyl]methoxy-tert-butyl-diphenylsilane	288578-81-4	C₄₅H₇₄O₃Si₃	747.337
——	(1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-1,4-bis-O-(triethylsilyl)-3-[(Z)-7-(methoxycarbonyl)hept-2-enyl]cyclopentane-1,4-diol	534584-74-2	C₄₃H₇₂O₅Si₃	753.298
——	(1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-3-[(Z)-5,5-bis(isopropyloxy)pent-2-enyl]-1,4-di-O-(triethylsilyl)cyclopentane-1,4-diol	213777-20-9	C₄₅H₇₈O₅Si₃	783.368
——	(1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-3-[(Z)-5-tetrahydropyranyloxypent-2-enyl]-1,4-bis(triethylsilyl)cyclopentane-1,4-diol	334670-37-0	C₄₄H₇₄O₅Si₃	767.325
——	(1S,2R,3R,4R)-1,4-di-O-benzoyl-2-(tert-butyldiphenylsilyloxymethyl)-3-(4-formylbutyl)cyclopentane-1,4-diol	213777-23-2	C₄₁H₄₆O₆Si	662.898
——	(1S,2R,3R,4R)-1,4-di-O-benzoyl-2-(tert-butyldiphenylsilyloxymethyl)-3-(4-methoxycarbonylbutyl)cyclopentane-1,4-diol	213777-24-3	C₄₂H₄₈O₇Si	692.924
——	(1S,2R,3R,4R)-1,4-di-O-benzoyl-2-(tert-butyldiphenylsilyloxymethyl)-3-[7-(methoxycarbonyl)heptyl]cyclopentane-1,4-diol	534584-82-2	C₄₅H₅₄O₇Si	735.005
——	[(1R,2R,3R,4S)-4-benzoyloxy-3-[[tert-butyl(diphenyl)silyl]oxymethyl]-2-[(Z)-oct-2-enyl]cyclopentyl] benzoate	377078-54-1	C₄₄H₅₂O₅Si	688.979
——	(1S,2R,3R,4R)-1,4-di-O-benzoyl-2-(tert-butyldiphenylsilyloxymethyl)-3-[(Z)-5-hydroxypent-2-enyl]cyclopentane-1,4-diol	334670-40-5	C₄₁H₄₆O₆Si	662.898
——	[(1R,2R,3R,4S)-4-benzoyloxy-3-[[tert-butyl(diphenyl)silyl]oxymethyl]-2-[(2Z,5Z,8Z)-undeca-2,5,8-trienyl]cyclopentyl] benzoate	288578-83-6	C₄₇H₅₄O₅Si	727.028
——	(1S,2R,3R,4R)-1,4-di-O-benzoyl-2-(tert-butyldiphenylsilyloxymethyl)-3-(5,5-diethoxypentyl)cyclopentane-1,4-diol	213777-22-1	C₄₅H₅₆O₇Si	737.021
——	(1S,2R,3R,4R)-1,4-di-O-benzoyl-2-(tert-butyldiphenylsilyloxymethyl)-3-[(Z)-4-methoxycarbonylbut-2-enyl]cyclopentane-1,4-diol	334670-41-6	C₄₂H₄₆O₇Si	690.909
——	(1S,2R,3R,4R)-1,4-di-O-benzoyl-2-(tert-butyldiphenylsilyloxymethyl)-3-[(Z)-5-tetrahydropyranyloxypent-2-enyl]cyclopentane-1,4-diol	334670-39-2	C₄₆H₅₄O₇Si	747.016

反应信息

作为反应物：

描述：

(1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-3-(formylmethyl)-1,4-bis-O-(triethylsilyl)cyclopentane-1,4-diol 在盐酸、 palladium on activated charcoal 、 (R)-BINAL-H 、氢气、 sodium hexamethyldisilazane 、双(三甲基硅烷基)氨基钾、戴斯-马丁氧化剂作用下，以四氢呋喃、吡啶、甲醇、乙醇、二氯甲烷为溶剂，反应 11.5h，生成 (1S,2S,3R,4R)-1,4-di-O-benzoyl-2-[(1E,3R)-3-hydroxypent-1-enyl]-3-[7-(methoxycarbonyl)heptyl]cyclopentane-1,4-diol

参考文献：

名称：

Total synthesis of phytoprostane F1 and its 16 epimer

摘要：

The first synthesis of the two enantiomers of phytoprostane F-1 methyl ester 1 and 2 is described using the syn-anti-syn alcoxy ester 3 as starting material. (C) 2003 Elsevier Science Ltd. All rights reserved.

DOI：

10.1016/s0040-4039(03)00171-0
作为产物：

描述：

(1S,2S,3R,4R)-1,4-Bis(triethylsilyloxy)-3-(methoxycarbonylmethyl)-2-tert-butyldiphenylsilyloxymethylcyclopentane 在二异丁基氢化铝作用下，以甲苯为溶剂，反应 0.5h，以93%的产率得到(1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-3-(formylmethyl)-1,4-bis-O-(triethylsilyl)cyclopentane-1,4-diol

参考文献：

名称：

15-F2t-异前列烷四种代谢物的全合成

摘要：

描述了 15F2t-isoprostane - 2,3-dinor-5,6-dihydro-15F2t-isoprostane 1 和 2,3-dinor-15F2t-isoprostane 2 - 的两种主要尿液代谢物的对映异构体甲酯的全合成其他相关的推定代谢物 (15R)/(15S)-2,3-dinor-5,6,13,14-tetrahydro-15F2t-isoprostane 3 和 2,3-dinor-5,6,13,14-tetrahydro -15-oxo-15F2t-isoprostane 4. 合成，从双丙酮 D-葡萄糖开始，包括作为其主要步骤的高度官能化前体的自由基环化反应，然后是使用磷合成子的 Wittig 和/或 Horner-Wadsworth-Emmons 延伸。这里合成的化合物已被用作研究 15F2t-异前列烷和 ent-15F2t-异前列烷代谢的参考化合物。

DOI：

10.1002/1099-0690(200102)2001:4<809::aid-ejoc809>3.0.co;2-6

点击查看最新优质反应信息

文献信息

Total synthesis of 4(RS)-F4t-isoprostane methyl ester

作者：Thierry Durand、Alexandre Guy、Jean-Pierre Vidal、Jacques Viala、Jean-Claude Rossi

DOI：10.1016/s0040-4039(00)00508-6

日期：2000.5

The first total synthesis of 4(RS)-F4t-isoprostane methyl ester 1 is described using diacetone-d-glucose as starting material. This new isoprostane (neuroprostane) would be very useful in neurological studies as a potent lipid peroxidation index to obtain an integrated assessment of oxidative stress in the human brain.

4的第一个全合成（RS）-F 4吨-isoprostane甲酯1使用双丙酮d-葡萄糖作为起始材料进行说明。这种新的异前列腺素（neuroprostane）作为有效的脂质过氧化指数，在神经学研究中非常有用，可以对人脑中的氧化应激进行综合评估。
Total Synthesis of the Eight Diastereomers of the Syn-Anti-Syn Phytoprostanes F<sub>1</sub> Types I and II

作者：Siham El Fangour、Alexandre Guy、Valérie Despres、Jean-Pierre Vidal、Jean-Claude Rossi、Thierry Durand

DOI：10.1021/jo035638i

日期：2004.4.1

Syntheses of the eight enantiomerically pure diastereomers of the syn-anti-syn phytoprostanes F-1 types I and II are described starting from D- and L-glucose. Key steps include Wittig coupling, Horner Wadsworth Emmons (HWE) reactions, and enantioselective reduction of alpha,beta-unsaturated ketones.
Total synthesis of ent -15(RS)-2,3-dinor-5,6-dihydro-8- epi -PGF2α

作者：Alexandre Guy、Thierry Durand、Arlene Roland、Emmanuelle Cormenier、Jean-Claude Rossi

DOI：10.1016/s0040-4039(98)01290-8

日期：1998.8

The first total synthesis of ent-15(RS) 2,3-dinor-5,6-dihydro-8-epi-PGF2 alpha 1 is described using diacetone-D-glucose as starting material. The major urinary metabolite of the isoprostane 8-epi-PGF2 alpha is 2,3-dinor-5,6-dihydro-8-epi-PGF2 alpha, which is a potent lipid peroxidation index to obtain an integrated assessment of oxidative stress in humans. (C) 1998 Elsevier Science Ltd. All rights reserved.
Syntheses and preliminary pharmacological evaluation of the two epimers of the 5-F2t-isoprostane

作者：Thierry Durand、Jean-Luc Cracowski、Alexandre Guy、Jean-Claude Rossi

DOI：10.1016/s0960-894x(01)00473-5

日期：2001.9

The total synthesis of the 5-F-2t-isoprostane I and its 5-epimer 2 from diacetone-D-glucose is described. We report preliminary data on the vascular properties of these compounds. (C) 2001 Elsevier Science Ltd. All rights reserved.