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methyl 4,6-O-[(R)-(4-methoxyphenyl)methylene]-α-D-glucopyranoside | 162680-20-8

分子结构分类

有机化合物 - 有机杂环化合物 - 吡喃二恶英

中文名称

——

中文别名

——

英文名称

methyl 4,6-O-[(R)-(4-methoxyphenyl)methylene]-α-D-glucopyranoside

英文别名

methyl 4,6-O-(4’-methoxybenzylidene)-α-D-glucopyranoside；methyl 4,6-O-(4′-Methoxybenzylidine)-α-D-glucopyranoside；methyl 4,6-O-((4-methoxyphenyl)methylene)-α-D-glucopyranoside；methyl 4,6-O-(4-methoxy)benzylidene-α-D-galactopyranoside；methyl 4,6-O-(4-methoxy)benzylidene α-D-glucopyranoside；methyl 4,6-O-(4-methoxybenzylidene)-α-D-glucopyranoside；(2R,4aR,6S,7R,8R,8aS)-6-Methoxy-2-(4-methoxyphenyl)hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol；(2R,4aR,6S,7R,8R,8aS)-6-methoxy-2-(4-methoxyphenyl)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol

methyl 4,6-O-[(R)-(4-methoxyphenyl)methylene]-α-D-glucopyranoside化学式

CAS

162680-20-8

化学式

C₁₅H₂₀O₇

mdl

——

分子量

312.32

InChiKey

RFXAHIIJEKSSSM-OJVARPOJSA-N

BEILSTEIN

——

EINECS

——

物化性质

熔点：

197-198 °C
沸点：

504.7±50.0 °C(Predicted)
密度：

1.36±0.1 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

-0.2
重原子数：

22
可旋转键数：

3
环数：

3.0
sp3杂化的碳原子比例：

0.6
拓扑面积：

86.6
氢给体数：

2
氢受体数：

7

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
alpha-甲基葡萄糖甙	methyl-alpha-D-glucopyranoside	97-30-3	C₇H₁₄O₆	194.185

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	methyl 3-O-benzyl-4,6-O-(p-methoxybenzylidene)-α-D-glucopyranoside	162583-80-4	C₂₂H₂₆O₇	402.444
——	methyl 2,3-di-O-methyl-4,6-O-p-methoxybenzylidene-α-D-glucopyranoside	221690-32-0	C₁₇H₂₄O₇	340.373
——	methyl 2-O-benzyl-4,6-O-(p-methoxybenzylidene)-α-D-glucopyranoside	162583-81-5	C₂₂H₂₆O₇	402.444
——	methyl 4,6-O-(4-methoxybenzylidene)-2,3-di-O-tetradecyl-α-D-glucopyranoside	872677-64-0	C₄₃H₇₆O₇	705.072
——	methyl 2,3- di-O-n-octyl-4,6-O-p-methoxybenzylidene-α-D-glucopyranoside	1619942-43-6	C₃₁H₅₂O₇	536.75
——	methyl-2,3-bis-O-benzyl-4,6-O-[(R)-(4-methoxyphenyl)methylene]-α-D-glucopyranoside	90633-88-8	C₂₉H₃₂O₇	492.569
——	methyl 4,6-di-O-methoxybenzylidene-2,3-di-O-methoxybenzyl-α-D-glucopyranoside	342789-77-9	C₃₁H₃₆O₉	552.621
——	(2R,4aR,6S,7R,8S,8aR)-6-methoxy-2-(4-methoxyphenyl)-8-[(4-methoxyphenyl)methoxy]-7-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine	162583-82-6	C₃₀H₃₄O₈	522.595
——	methyl 3-O-benzyl-2-deoxy-4,6-O-(p-methoxybenzylidene)-α-D-glucopyranoside	177554-76-6	C₂₂H₂₆O₆	386.445
——	(2R,4aR,6S,7R,8aS)-7-Benzyloxy-6-methoxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxine	177554-82-4	C₂₂H₂₆O₆	386.445
——	methyl 2,3-anhydro-4,6-O-(4-methoxy)benzylidene-α-D-allopyranoside	128142-73-4	C₁₅H₁₈O₆	294.304
——	Acetic acid (2R,4aR,6S,7R,8S,8aS)-8-hydroxy-6-methoxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester	637316-89-3	C₁₇H₂₂O₈	354.357
——	methyl 2,3-di-O-acetyl-4,6-O-p-methoxybenzylidene-α-D-glucopyranoside	302783-17-1	C₁₉H₂₄O₉	396.394
——	methyl 2,3-di-O-methyl-4-O-p-methoxybenzyl-α-D-glucopyranoside	66728-83-4	C₁₇H₂₆O₇	342.389
——	methyl 3-O-benzyl-2-deoxy-4-O-(p-methoxybenzyl)-6-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-α-D-arabino-hexopyranoside	177554-87-9	C₅₆H₆₂O₁₁	911.102
——	methyl 2-O-benzyl-3-deoxy-4-O-(p-methoxybenzyl)-6-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-α-D-ribo-hexopyranoside	177554-88-0	C₅₆H₆₂O₁₁	911.102
——	methyl 2,3-di-O-octyl-4-O-p-methoxybenzyl-α-D-glucopyranoside	1619942-44-7	C₃₁H₅₄O₇	538.766
——	methyl 2,3-di-O-methyl-4-O-p-methoxybenzyl-6-O-(2,5,8,11,14-pentaoxaheptadec-16-ynyl)-α-D-glucopyranoside	1619942-51-6	C₂₈H₄₄O₁₁	556.651
——	methyl 2,3-di-O-benzyl-4-O-(p-methoxybenzyl)-α-D-glucopyranoside	——	C₂₉H₃₄O₇	494.585
——	methyl 2-O-benzyl-3,4-bis-O-(p-methoxybenzyl)-α-D-glucopyranoside	162583-79-1	C₃₀H₃₆O₈	524.611
——	Methyl 2,3,4-tri-O-(4-methoxybenzyl)-α-D-glucopyranoside	137915-48-1	C₃₁H₃₈O₉	554.637
——	methyl 2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-α-D-glucopyranoside	90633-94-6	C₂₉H₃₄O₇	494.585
——	methyl 2,3-di-O-octyl-4-O-p-methoxybenzyl-6-O-(2,5,8,11,14-pentaoxaheptadec-16-ynyl)-α-D-glucopyranoside	1619942-45-8	C₄₂H₇₂O₁₁	753.027
——	[(2R,4aR,6S,7R,8S,8aR)-7-benzoyloxy-6-methoxy-2-(4-methoxyphenyl)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] benzoate	1112986-37-4	C₂₉H₂₈O₉	520.536
——	[(2R,3S,4R,6S)-4-Benzyloxy-6-methoxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-methanol	177554-77-7	C₂₂H₂₈O₆	388.461
——	Dithiocarbonic acid O-[(2R,4aR,6S,7R,8S,8aR)-7-benzyloxy-6-methoxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl] ester S-methyl ester	177554-81-3	C₂₄H₂₈O₇S₂	492.614
——	Dithiocarbonic acid O-[(2R,4aR,6S,7R,8S,8aR)-8-benzyloxy-6-methoxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl] ester S-methyl ester	177554-75-5	C₂₄H₂₈O₇S₂	492.614
——	methyl 2-O-benzyl-6,7-dideoxy-3,4-bis-O-(p-methoxybenzyl)-α-D-gluco-hept-6-enopyranoside (1,5)	162583-83-7	C₃₁H₃₆O₇	520.623
2,3-二-o-苄基-alpha-d-吡喃葡萄糖苷甲酯	methyl 2,3-di-O-benzyl-α-D-glucopyranoside	17791-36-5	C₂₁H₂₆O₆	374.434
——	methyl 2-O-benzyl-3,4-bis-O-(p-methoxybenzyl)-α-D-gluco-hexodialdopyranoside (1,5)	183170-36-7	C₃₀H₃₄O₈	522.595
——	(2S,3S,4S,5R,6S)-6-Methoxy-3,4,5-tris-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carbaldehyde	137897-35-9	C₃₁H₃₆O₉	552.621
——	methyl 4-C-allyl-2,3-di-O-benzyl-6-O-(p-methoxybenzyl)-α-D-galactopyranoside	1610594-22-3	C₃₂H₃₈O₇	534.65
——	methyl 2,3-di-O-benzyl-trichloroacetimidate-α-D-glucopyranoside	666753-73-7	C₂₃H₂₆Cl₃NO₆	518.822
——	methyl 4-C-allyl-2,3-di-O-benzyl-6-O-(p-methoxybenzyl)-4-o-methyl-α-D-galactopyranoside	1610594-23-4	C₃₃H₄₀O₇	548.676
——	2,6-di-O-benzyloxymethyl-3,4,5-tri-O-p-methoxybenzyl-D-myo-inositol	137897-32-6	C₄₆H₅₂O₁₁	780.912
——	D-1-O-acetyl-2,6-di-O-benzyloxymethyl-3,4,5-tri-O-methoxybenzyl-myo-inositol	137897-36-0	C₄₈H₅₄O₁₂	822.95
——	methyl 2,3-di-O-benzyl-6-O-(p-methoxybenzyl)-α-D-xylohexopyranosid-4-ulose	127239-16-1	C₂₉H₃₂O₇	492.569
——	methyl 2,3-di-O-benzyl-α-D-glucopyranosiduronic acid	50711-26-7	C₂₁H₂₄O₇	388.417
——	1-O-methyl-2,3-di-O-benzyl-α-D-glucopyranuronic acid methyl ester	29398-07-0	C₂₂H₂₆O₇	402.444
——	methyl 4-C-allyl-2,3-di-O-benzyl-4-O-methyl-α-D-galactopyranoside	1610594-24-5	C₂₅H₃₂O₆	428.525
——	1-O-acetyl-3,4-bis-O-benzyl-5-O-[(4-methoxyphenyl)methyl]-D-myo-inositol	167394-68-5	C₃₀H₃₄O₈	522.595
——	D-1-O-acetyl-3,4,5-O-trimethoxybenzyl-myo-inositol	137897-31-5	C₃₂H₃₈O₁₀	582.648
——	methyl 2,3-di-O-benzyl-4-amino-4-deoxy-α-D-galactopyranoside	19877-40-8	C₂₁H₂₇NO₅	373.449
——	methyl 2,3-di-O-benzyl-α-D-xylo-hexopyranoside-4-ulose	223590-83-8	C₂₁H₂₄O₆	372.418
——	methyl 2,3-di-O-methyl-6-O-(2,5,8,11,14-pentaoxaheptadec-16-ynyl)-α-D-glucopyranoside	1619942-52-7	C₂₀H₃₆O₁₀	436.5
——	methyl 2,3-di-O-octyl-6-O-(2,5,8,11,14-pentaoxaheptadec-16-ynyl)-α-D-glucopyranoside	1619942-46-9	C₃₄H₆₄O₁₀	632.876
——	methyl 2,3-di-O-tetradecyl-α-D-glucopyranoside	150126-34-4	C₃₅H₇₀O₆	586.937
——	Bn(-2)[Bn(-3)][Tf(-4)][Cl3CC(NH)(-6)]a-Glc1Me	1053647-65-6	C₂₄H₂₅Cl₃F₃NO₈S	650.885
——	(1R,2S,3S,4R,5S)-3-(benzyloxy)-4-hydroxy-1,2-bis-<(p-methoxybenzyl)oxy>-5-vinylcyclopentane	221690-29-5	C₃₀H₃₄O₆	490.596
——	(Z)-methyl 6-O-acetyl-2,3,4-tri-O-methoxybenzyl-α-D-gluco-hex-5-enopyranoside	137897-29-1	C₃₃H₃₈O₁₀	594.659
——	(1R,2R,3S,4R,5S)-2-hydroxy-3,4,5-tri-O-(4-methoxybenzyl)-6-oxocyclohexyl acetate	137897-30-4	C₃₂H₃₆O₁₀	580.632
——	(2R,3R,4S,5R,6S)-2-acetoxy-3-hydroxy-4,5-bis-O-benzyl-6-O-[(4-methoxyphenyl)methyl]-cyclohexanone	161364-90-5	C₃₀H₃₂O₈	520.579
——	methyl 2,3-di-O-acetyl-α-D-glucopyranoside	29868-42-6	C₁₁H₁₈O₈	278.259
——	(2R,3R,4R,5R,6S)-4,5-Diacetoxy-3-[(2S,4aR,6R,7R,8S,8aS)-7,8-diacetoxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-ylsulfanyl]-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester	870192-84-0	C₃₀H₃₈O₁₆S	686.688
——	(2S,3R,4R,4aR,8aS)-3,4-bis(benzyloxy)-4a-hydroxy-2-methoxy-3,4,4a,8a-tetrahydro-2H-chromen-8(5H)-one	1610594-28-9	C₂₄H₂₆O₆	410.467

反应信息

作为反应物：

描述：

methyl 4,6-O-[(R)-(4-methoxyphenyl)methylene]-α-D-glucopyranoside 在草酰氯、三氟化硼乙醚、 sodium acetate 、 mercury(II) trifluoroacetate 、双(三甲基硅烷基)氨基钾、三乙酰氧基硼氢化钠、 sodium hydride 、溶剂黄146 、二甲基亚砜、三乙胺作用下，以四氢呋喃、二氯甲烷、水、 N,N-二甲基甲酰胺、丙酮、甲苯、乙腈、 mineral oil 为溶剂，反应 27.25h，生成 1-O-acetyl-3,4-bis-O-benzyl-5-O-[(4-methoxyphenyl)methyl]-D-myo-inositol

参考文献：

名称：

不对称取代的鞘氨醇的合成

摘要：

鲨肌醇，肌醇家族的一个罕见构件，存在于axinelloside A，海洋代谢物与针对人端粒酶有趣的抑制活性。在这里，我们提出了从廉价的d-葡萄糖开始的不对称取代的鞘氨醇的简洁合成方法。我们的合成方法利用了乙酸乙烯酯的Ferrier重排和生成酮的立体选择性还原，从而建立了鞘氨醇的核心。该协议可从市售材料中以10个步骤访问大量的鞘氨醇。

DOI：

10.1016/j.tetlet.2016.06.038
作为产物：

描述：

alpha-甲基葡萄糖甙、 P-(甲氧基甲基)苯甲醚以49%的产率得到

参考文献：

名称：

OIKAWA, YUJI;NISHI, TAKAO;YONEMITSU, OSAMU, TETRAHEDRON LETT., 1983, 24, N 37, 4037-4040

摘要：

DOI：

点击查看最新优质反应信息

文献信息

Site-Selective and Stereoselective <i>O</i>-Alkylation of Glycosides by Rh(II)-Catalyzed Carbenoid Insertion

作者：Jicheng Wu、Xiaolei Li、Xiaotian Qi、Xiyan Duan、Weston L. Cracraft、Ilia A. Guzei、Peng Liu、Weiping Tang

DOI：10.1021/jacs.9b11262

日期：2019.12.18

most prevalent trans-1,2-diols in various pyranoses can be systematically and predictably differentiated based on the model derived from DFT calculations. We also demonstrated that the selective O-alkylation method could significantly improve the efficiency and stereoselectivity of glycosylation reactions. The alkyl groups introduced to carbohydrates by OH insertion reaction can serve as functional

碳水化合物是具有合成挑战性的分子，在所有生命系统中都具有重要的生物学作用。碳水化合物的选择性合成和功能化提供了巨大的机会来提高我们对这一类基本重要分子的生物学功能的理解。然而，碳水化合物中看似相同的羟基的选择性官能化仍然是化学合成中长期存在的挑战。我们在此描述了一种实用且可预测的方法，用于通过 Rh(II) 催化插入金属卡宾中间体对碳水化合物羟基进行位点和立体选择性烷基化。这代表了对碳水化合物进行系统修饰的最温和的烷基化方法之一。密度泛函理论 (DFT) 计算表明，位点选择性是在 Rh(II)-carbenoid 插入步骤中确定的，该步骤更喜欢插入具有相邻轴向取代基的羟基。随后的分子内烯醇质子化决定了意想不到的高立体选择性。基于从 DFT 计算得出的模型，可以系统地和可预测地区分各种吡喃糖中最普遍的反式 1,2-二醇。我们还证明了选择性 O-烷基化方法可以显着提高糖基化反应的效率和立体选择性。通过
Stripping off Water at Ambient Temperature: Direct Atom-Efficient Acetal Formation between Aldehydes and Diols Catalyzed by Water-Tolerant and Recoverable Vanadyl Triflate

作者：Chien-Tien Chen、Shiue-Shien Weng、Jun-Qi Kao、Chun-Cheng Lin、Mi-Dan Jan

DOI：10.1021/ol051178z

日期：2005.7.1

catalyst can be readily recovered from the aqueous layer. In combination with vanadyl triflate-catalyzed sequential regioselective, reductive acetal opening and chemoselective acylations, the title method allows for differential functionalization of all four hydroxyl units in a given glucopyranoside.

[反应：请参见文字]。通过使用三氟甲磺酸钒在环境温度下在CH（3）CN中作为催化剂，可以很容易地用1,2-和1,3-二醇将芳香醛保护为缩醛。基于碳水化合物的1,2-和1,3-二醇同样可以得到很好的保护。催化剂可以容易地从水层中回收。与三氟甲磺酸氧钒催化的顺序区域选择性，还原性乙缩醛开放和化学选择性酰化相结合，该标题方法可在给定的吡喃葡萄糖苷中实现所有四个羟基单元的差异化功能化。
2,4,6-Trichloro-1,3,5-triazine (TCT) mediated one-pot sequential functionalisation of glycosides for the generation of orthogonally protected monosaccharide building blocks

作者：Madhubabu Tatina、Syed Khalid Yousuf、Debaraj Mukherjee

DOI：10.1039/c2ob25452b

日期：——

Orthogonally protected monosaccharide building blocks have been prepared using TCT in a one-pot multicomponent transformation. The process involves successive steps of arylidene acetalation, esterification and regioselective reductive acetal cleavage. High regioselectivity, scope for using a broad range of substrates, functional group tolerance, mild reaction conditions, easy handling process and wide application range are a few advantages of the current process.

利用TCT（三氯乙酰亚胺基）在一锅多组分转化中制备了正交保护的单糖构建块。该过程包括连续的芳亚基缩醛化、酯化和区域选择性还原开环反应步骤。高区域选择性、广泛的底物适用范围、官能团的耐受性、温和的反应条件、易于操作以及广泛的应用范围是该当前过程的一些优点。
Asymmetric hydrogenation - influence of the structure of carbohydrate derived catalysts on the relative enantioselectivity QH/Me regarding acid and ester substrates and its inversion - selectivity increase in water by amphiphiles

作者：Rüdiger Selke、Manuela Ohff、Andreas Riepe

DOI：10.1016/s0040-4020(96)00953-2

日期：1996.11

resulting in an unusual low relative enantioselectivityQ=qH/qMe of 0.3 for the precatalysts 4e and 4f. Deprotected, 4,6-OH-group bearing catalysts 1-4g,h generally show smaller differences of %ee in methanol or benzene, however, not in water. Under addition of amphiphiles a in comparison with blanks b the relative enantioselectivity Q=qa/qb clearly increases for both groups of catalysts - in most cases

4,6 - O-苄叉基保护的2,3-双（O-二苯基膦基）-δ-吡喃葡萄糖苷铑（I）螯合物预催化剂1-4e ，f显示了对（Z）-2- N-酰氨基丙烯酸甲酯的加氢作用6 -8随轴向取向的六吡喃糖苷取代基数量的增加，对映选择性逐步降低。对于类似的底物酸6h-8h的降低甚至更强，导致预催化剂4e和4f的相对低的相对对映选择性Q = q H / q Me为0.3。脱保护的含4,6-OH基的催化剂1-4g，h通常在甲醇或苯中显示出较小的％ee差异，而在水中则显示出较小的％ee差异。与空白b相比，在添加两亲性a的情况下，两组催化剂的相对对映选择性Q = q a / q b明显增加-在大多数情况下，Q值在3到8之间-与催化剂的中性或离子性质无关两亲的。
Novel Synthesis of Enantiomerically Pure Natural Inositols and Their Diastereoisomers

作者：Hideyo Takahashi、Hisae Kittaka、Shiro Ikegami

DOI：10.1021/jo001575h

日期：2001.4.1

phosphoinositide signaling system has been discovered in the past 10 years, many factors remain unclear. For this reason, there is an increased demand for supplies of D-myo-inositol and particularly of novel analogues to investigate these biological mechanisms in more detail. Herein, we report the efficient syntheses of all diastereoisomers of inositol starting with 6-O-acetyl-5-enopyranosides. Conversion

已经发现各种肌醇多磷酸盐引发许多重要的生物学过程。尽管在过去的十年中已经发现了这种磷酸肌醇信号系统的知识，但许多因素仍不清楚。由于这个原因，对D-肌醇特别是新颖类似物的供应的需求增加，以更详细地研究这些生物学机制。在此，我们报告了从6-O-乙酰基-5-烯吡喃糖苷开始的肌醇所有非对映异构体的高效合成。发现用催化量的二氯化钯可以有效地进行6-O-乙酰基-5-烯吡喃糖苷到相应的取代的环己酮的转化（费里尔-II重排）。所获得的β-羟基酮的立体选择性还原提供了所有肌醇非对映异构体的前体，具有良好至优异的产率以及高的立体选择性。这些对映体纯的肌醇非对映异构体的良好可及性导致D-肌醇1,4,5-三磷酸和D-肌醇1,3,4,5-四磷酸的有效合成。