1L-3,4:5,6-Di-O-isopropyliden-2-O-methyl-chiro-inosit | 58769-23-6

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

1L-3,4:5,6-Di-O-isopropyliden-2-O-methyl-chiro-inosit

英文别名

(1R,2R,6R,7S,8R,9S)-8-methoxy-4,4,11,11-tetramethyl-3,5,10,12-tetraoxatricyclo[7.3.0.02,6]dodecan-7-ol

1L-3,4:5,6-Di-O-isopropyliden-2-O-methyl-chiro-inosit化学式

CAS

58769-23-6

化学式

C₁₃H₂₂O₆

mdl

——

分子量

274.314

InChiKey

IPNUFAHKROGNMZ-OVHRRVLLSA-N

BEILSTEIN

——

EINECS

——

物化性质

沸点：

374.1±42.0 °C(Predicted)
密度：

1.24±0.1 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

0
重原子数：

19
可旋转键数：

1
环数：

3.0
sp3杂化的碳原子比例：

1.0
拓扑面积：

66.4
氢给体数：

1
氢受体数：

6

上下游信息

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	1D-3-deoxy-1,2:5,6-di-O-isopropylidene-4-O-methyl-myo-inositol	97087-18-8	C₁₃H₂₂O₅	258.315
——	1L-1,2-O-isopropylidene-5,6-di-O-methyl-chiro-inositol	142543-92-8	C₁₁H₂₀O₆	248.276
——	1D-(1,2,5/3,4)-3,4-O-isopropylidene-1,2-di-O-methylcyclohexanepentaol	135131-63-4	C₁₁H₂₀O₅	232.277
——	1D-1,2-anhydro-5,6-O-isopropylidene-3,4-di-O-methyl-allo-inositol	142543-93-9	C₁₁H₁₈O₅	230.261
——	1L-1-O-acetyl-3,4:5,6-di-O-isopropylidene-2-O-methyl-chiro-inositol	134235-44-2	C₁₅H₂₄O₇	316.351
——	[(3aS,4S,5S,6R,7R,7aS)-6,7-dihydroxy-5-methoxy-2,2-dimethyl-3a,4,5,6,7,7a-hexahydro-1,3-benzodioxol-4-yl] acetate	108852-39-7	C₁₂H₂₀O₇	276.287
——	1D-4-O-benzyl-1,2:5,6-di-O-isopropylidene-3-deoxy-myo-inositol	148888-38-4	C₁₉H₂₆O₅	334.412
——	(3aR,4R,4aR,7aR,8S,8aS)-8-Benzyloxy-2,2,6,6-tetramethyl-hexahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-4-ol	192122-41-1	C₁₉H₂₆O₆	350.412
——	1D-6-O-benzyl-3-deoxy-1,2-O-isopropylidene-myo-inositol	148888-41-9	C₁₆H₂₂O₅	294.348
——	1L-1-C-Hydroxymethyl-2,3:4,5-di-O-isopropyliden-6-O-methyl-myo-inosit	75348-10-6	C₁₄H₂₄O₇	304.34
——	1D-4-O-benzyl-3-deoxy-1,2-O-isopropylidene-myo-inositol	148888-40-8	C₁₆H₂₂O₅	294.348
——	1L-1-C-Hydroxymethyl-1,7:2,3:4,5-tri-O-iospropyliden-6-O-methyl-myo-inosit	80970-89-4	C₁₇H₂₈O₇	344.405
——	1L-1,7-Anhydro-1-C-hydroxymethyl-2,3:4,5-di-O-isopropyliden-6-O-methyl-myo-inosit	75251-60-4	C₁₄H₂₂O₆	286.325
——	2L-(2,3,5/4,6)-2,3:4,5-di-O-isopropylidene-6-O-methylpentahydroxycyclohexanone	75348-09-3	C₁₃H₂₀O₆	272.298
——	1L-7-O-Acetyl-1-C-hydroxymethyl-2,3:4,5-di-O-isopropyliden-6-O-methyl-myo-inosit	80970-91-8	C₁₆H₂₆O₈	346.378
——	(1R,2R,6R,7R,8R,9S)-8-[(4-methoxyphenyl)methoxy]-4,4,11,11-tetramethyl-3,5,10,12-tetraoxatricyclo[7.3.0.02,6]dodecan-7-ol	260976-22-5	C₂₀H₂₈O₇	380.438
——	(3aR,4S,5R,5aS,8aR,8bR)-5-(4-Methoxy-benzyloxy)-2,2,7,7-tetramethyl-hexahydro-benzo[1,2-d;3,4-d']bis[1,3]dioxol-4-ol	260976-21-4	C₂₀H₂₈O₇	380.438
——	1D-(1,2,5/3,4)-3,4-O-isopropylidene-5-O-(p-methoxybenzyl)-1,2-di-O-methylcyclohexanepentaol	135131-64-5	C₁₉H₂₈O₆	352.428
——	(3aS,4R,5R,5aR,8aR,8bR)-4,5-Bis-(4-methoxy-benzyloxy)-2,2,7,7-tetramethyl-hexahydro-benzo[1,2-d;3,4-d']bis[1,3]dioxole	260976-23-6	C₂₈H₃₆O₈	500.589
——	D-3-Chloro-3-deoxy-1,2:4,5-di-O-isopropylidene-myo-inositol	150491-89-7	C₁₂H₁₉ClO₅	278.733
——	[(1R,2S,6S,7S,8S,9S)-8-hydroxy-4,4,11,11-tetramethyl-3,5,10,12-tetraoxatricyclo[7.3.0.02,6]dodecan-7-yl] methanesulfonate	156672-20-7	C₁₃H₂₂O₈S	338.379
——	[(1R,2S,6S,7S,8S,9S)-8-methoxy-4,4,11,11-tetramethyl-3,5,10,12-tetraoxatricyclo[7.3.0.02,6]dodecan-7-yl] methanesulfonate	134182-86-8	C₁₄H₂₄O₈S	352.406
——	1D-6-O-benzyl-3-deoxy-2-O-(ethoxyethyl)-myo-inositol	148888-45-3	C₁₇H₂₆O₆	326.39
——	Methyl-2,3,4-tri-O-benzyl-6-O-(1L-3,4:5,6-di-O-isopropyliden-2-O-methyl-chiro-inosit-1-yl)-α-D-glucopyranosid	104976-33-2	C₄₁H₅₂O₁₁	720.857
——	1L-3-O-benzoyl-1,2-O-isopropylidene-5,6-di-O-methyl-chiro-inositol	135131-61-2	C₁₈H₂₄O₇	352.384
——	1D-4,5-di-O-benzoyl-6-O-benzyl-3-deoxy-1,2-O-isopropylidene-myo-inositol	132662-65-8	C₃₀H₃₀O₇	502.564
——	Methanesulfonic acid (3aS,4R,4aS,7aR,8S,8aS)-8-hydroxy-2,2,6,6-tetramethyl-hexahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-4-yl ester	156672-21-8	C₁₃H₂₂O₈S	338.379
——	1D-5,6-di-O-benzoyl-4-O-benzyl-3-deoxy-1,2-O-isopropylidene-myo-inositol	132662-66-9	C₃₀H₃₀O₇	502.564
——	1D-(1,2,5/3,4)-5-O-(p-methoxybenzyl)-1,2-di-O-methyl-3-O-(tetrahydropyran-2-yl)cyclohexanepentaol	135131-66-7	C₂₁H₃₂O₇	396.481
——	1L-3,4:5,6-Di-O-isopropyliden-2-O-methyl-1-O-<(trifluormethyl)sulfonyl>-chiro-inosit	97119-80-7	C₁₄H₂₁F₃O₈S	406.377
——	[(3aS,4S,5R,6R,7S,7aR)-6-benzoyloxy-7-[(4-methoxyphenyl)methoxy]-2,2-dimethyl-4-phenylmethoxy-3a,4,5,6,7,7a-hexahydro-1,3-benzodioxol-5-yl] benzoate	1053697-81-6	C₃₈H₃₈O₉	638.714
——	1L-1-Azido-1-desoxy-2,3:4,5-di-O-isopropyliden-6-O-methyl-myo-inosit	97169-82-9	C₁₃H₂₁N₃O₅	299.327
——	1D-1,4,5-tri-O-benzoyl-6-O-benzyl-3-deoxy-2-O-(1-ethoxyethyl)-myo-inositol	148888-44-2	C₃₈H₃₈O₉	638.714
——	(3aS,4R,5S,5aR,8aR,8bS)-5-Methoxy-2,2,7,7-tetramethyl-4-trifluoromethyl-hexahydro-benzo[1,2-d;3,4-d']bis[1,3]dioxol-4-ol	192068-39-6	C₁₄H₂₁F₃O₆	342.312

反应信息

作为反应物：

描述：

1L-3,4:5,6-Di-O-isopropyliden-2-O-methyl-chiro-inosit 在 lithium aluminium tetrahydride 、锂硼氢、草酰氯、 TEA 、 camphor-10-sulfonic acid 、三溴化硼、 sodium hydride 、二甲基亚砜、二异丙胺作用下，以四氢呋喃、二氯甲烷、 N,N-二甲基甲酰胺为溶剂，反应 19.0h，生成 (+/-)-6-O-benzyl-1,2:4,5-di-O-isopropylidene-3-O-p-methoxybenzyl-myo-inositol

参考文献：

名称：

Tools for Cell Signaling: Synthesis of the 3-Phosphatase-Resistant 1,3,4,5-InsP4 Mimic, 1D-myo-Inositol 1,4,5-Trisphosphate 3-Phosphorothioate

摘要：

The synthesis of 1D-myo-inositol 1,4,5-trisphosphate 3-phosphorothioate, a 3-phosphatase-resistant analogue of 1,3,4,5-InsP(4) is reported, and this compound is shown to elicit Ca-45(2+) release with an EC(50) which is comparable to that of the natural metabolite, thus supporting the idea that 1,3,4,5-InsP(4) can interact with the 1,4,5-InsP(3) receptors.

DOI：

10.1021/jo00088a003
作为产物：

描述：

L-白雀木醇、 2,2-二甲氧基丙烷在对甲苯磺酸作用下，以 N,N-二甲基甲酰胺为溶剂，反应 30.0h，生成 1L-3,4:5,6-Di-O-isopropyliden-2-O-methyl-chiro-inosit

参考文献：

名称：

肌醇衍生物缩合的巯基苯并噻唑和巯基苯并咪唑的合成

摘要：

这项工作描述了与2-巯基苯并噻唑或2-巯基苯并咪唑（潜在的抗菌剂）缩合的肌醇衍生物的合成。通过制备这些化合物的开环的环氧化物中间体（2小号，3 - [R -环氧-1- ö甲基升-手性肌醇和2 - [R，3 s ^ -环氧-1- ö甲基升-手性肌醇），其为得自升-quebrachitol（1- Ò甲基手性-肌醇）。用微波辐射促进缩合反应。

DOI：

10.1002/jhet.1096

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文献信息

Synthesis of D-3-deoxy-myo-inositol 1,4,5-trisphosphate and its effect on Ca2+ release in NIH 3T3 cells

作者：Markus J. Seewald、Ibrahim A. Aksoy、Garth Powis、Abdul H. Fauq、Alan P. Kozikowski

DOI：10.1039/c39900001638

日期：——

The synthesis of D-3-deoxy-myo-inositol 1,4,5-trisphosphate is reported together with its effect on Ca2+ release in permeabilized NIH 3T3 cells.

d-3 -脱氧的合成肌肉肌醇1,4,5-三磷酸与其对Ca效果一起报告2+在透化的NIH 3T3细胞的释放。
Synthesis of 1D-3-deoxy-, 1D-2,3-dideoxy-, and 1D-2,3,6-trideoxy-myo-inositol 1,4,5-trisphosphate from quebrachitol, their binding affinities, and calcium release activity

作者：A. P. Kozikowski、V. I. Ognyanov、A. H. Fauq、S. R. Nahorski、R. A. Wilcox

DOI：10.1021/ja00064a002

日期：1993.6

Syntheses of three optically pure, deoxygenated myo-inositol 1,4,5-trisphosphate analogues from quebrachitol are reported together with their binding affinities and 45 Ca 2+ release activity. The ligand-binding affinities of the analogues were determined using membrane preparations from bovine adrenal cortex. The 45 Ca 2+ release activities were compared to that of Ins(1,4,5)P 3 , using the calcium

三种光学纯的、脱氧的肌醇 1,4,5-三磷酸酯类似物的合成与它们的结合亲和力和 45 Ca 2+ 释放活性一起报告。使用来自牛肾上腺皮质的膜制剂测定类似物的配体结合亲和力。45 Ca 2+ 释放活性与Ins(1,4,5)P 3 的释放活性进行了比较，使用皂苷透化的SH-SY5Y人神经母细胞瘤细胞的钙动员受体。1D-3-deoxy-Ins(1,4,5)P 3 (16) 和 1D-2,3-dideoxy-Ins(1,4,5)P 3 (11) 表现出非常有效的配体和激动剂特性，而1D-2,3,6-trideoxy-Ins(1,4,5)P 3 (19) 的效力要低得多。这些数据为 Ins(1,4,5)P 3 的 HO-6 在其结合亲和力和 Ca 2+ 动员活性中发挥的关键作用提供了确凿的证据
Synthesis of several optically active O-methyl-inosamines and -inosadiamines from l-quebrachitol

作者：Seiichiro Ogawa、Akihiro Isaka

DOI：10.1016/0008-6215(91)80116-5

日期：1991.3

the di-O-isopropylidene derivative of the cyclitol. Nucleophilic displacement of these sulfonates with azide ion in 2-methoxyethanol produced the azido compounds, hydrogenolysis of which with Raney nickel, followed by acetylation, gave thirteen optically active O-methyl-inosamine and two O-methyl-inosadiamine derivatives. The structures of the new aminocyclitols were established on the basis of 1H-n

从环糖醇的二-O-异亚丙基衍生物开始，制备了一系列1-槲皮醇的对甲苯磺酸酯和甲磺酸酯。在2-甲氧基乙醇中用叠氮化物离子对这些磺酸盐进行亲核置换，生成了叠氮基化合物，将其与阮内镍氢解，然后进行乙酰化，得到了十三种光学活性的O-甲基-肌醇二胺和两个O-甲基-肌醇二胺衍生物。基于相应的过-O-乙酰基衍生物的1H-nmr光谱数据，确定了新的氨基环糖醇的结构。讨论了取代反应的机理，主要涉及邻近基团的参与。
Total synthesis of simmondsin

作者：Noritaka Chida、Ken Yamada、Seiichiro Ogawa

DOI：10.1039/c39910000588

日期：——

The first total synthesis of the naturally occurring cyanoglucoside, simmondsin 1, starting from L-quebrachitol and D-glucose, is described, revealing the absolute configuration of this compound.

该研究首次以 L-曲布其糖醇和 D-葡萄糖为起点，全合成了天然存在的氰基葡萄糖苷--西蒙德新 1，揭示了这种化合物的绝对构型。
Experimental and Theoretical Investigation of Epoxide Quebrachitol Derivatives Through Spectroscopic Analysis

作者：Mauro V. De Almeida、João Vitor De Assis、Mara Rubia C. Couri、Cleber P. A. Anconi、Mário C. Guerreiro、Hélio F. Dos Santos、Wagner B. De Almeida

DOI：10.1021/ol102305x

日期：2010.12.3

Two synthetic epoxide derivatives, important intermediates in organic synthesis, were obtained from l-quebrachitol, and their conformations were proposed based on spectroscopic analysis. Density functional theory (DFT) calculations of infrared and NMR spectra were shown to be reliable enough for organic chemistry applications. The observed structures were determined with the aid of the DFT spectroscopic

从1-槲皮醇中获得了两种合成的环氧化物衍生物，它们是有机合成中的重要中间体，并在光谱分析的基础上提出了它们的构象。红外和NMR光谱的密度泛函理论（DFT）计算显示出对于有机化学应用足够可靠。借助DFT光谱数据确定了观察到的结构，强调了组合的实验/理论研究的相关性和实用性，以及13 C NMR B3LYP / 6-31G（d，p）计算的实用性。