1,5-Anhydro-2-deoxy-4,6-O-(phenylmethylene)-D-arabino-hexopyranoside | 135214-83-4

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

1,5-Anhydro-2-deoxy-4,6-O-(phenylmethylene)-D-arabino-hexopyranoside

英文别名

O⁴,O⁶-((R)-benzylidene)-D-arabino-1,5-anhydro-2-deoxy-hexitol；O⁴,O⁶-((R)-Benzyliden)-D-arabino-1,5-anhydro-2-desoxy-hexit；(2R,4aR,8R,8aS)-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-ol

1,5-Anhydro-2-deoxy-4,6-O-(phenylmethylene)-D-arabino-hexopyranoside化学式

CAS

135214-83-4

化学式

C₁₃H₁₆O₄

mdl

——

分子量

236.268

InChiKey

HFOKDFALFAKRNI-FVCCEPFGSA-N

BEILSTEIN

——

EINECS

——

计算性质

辛醇/水分配系数(LogP)：

0.8
重原子数：

17
可旋转键数：

1
环数：

3.0
sp3杂化的碳原子比例：

0.54
拓扑面积：

47.9
氢给体数：

1
氢受体数：

4

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
——	1,5-anhydro-2-deoxy-4,6-O-benzylidene-D-ribohexitol	119238-15-2	C₁₃H₁₆O₄	236.268
——	3-O-benzoyl-4,6-O-benzylidene-1,2-dideoxy-D-glucopyranose	438216-14-9	C₂₀H₂₀O₅	340.376
——	(2R,4aR,8aR)-2-phenyl-4a,6,7,8a-tetrahydro-4H-pyrano[3,2-d][1,3]dioxin-8-one	63554-21-2	C₁₃H₁₄O₄	234.252
——	(2R,3R,4S,5R,6R)-2-[(2R,3S,4R)-2-Benzyloxymethyl-3-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol	252896-25-6	C₄₆H₅₆O₁₃	816.943
——	(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-O-(1->4)-6-O-benzyl-1,2,-dideoxy-D-glucopyranose	438216-17-2	C₄₀H₄₆O₈	654.8
——	3-O-benzoyl-6-O-benzyl-1,2-dideoxy-D-glucopyranose	438216-15-0	C₂₀H₂₂O₅	342.392
——	(4,6-O-benzylidene-3-O-[(S)-1-(oxycarbonyl)-2-cyclohexylethyloxy]-β-D-galactopyranosyl-O-(1->3)-[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-O-(1->4)]-6-O-benzyl-1,2-dideoxy-D-glucopyranose	438216-20-7	C₆₂H₇₄O₁₅	1059.26
——	(2S,3R,4aR,8S,8aR)-2-[(2R,3S,4S,4aS,6R,8aS)-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-2,3,4,4a,6,7,8,8a-octahydropyrano[3,2-b]pyran-6-yl]-8-chloro-2,3,4,4a,6,7,8,8a-octahydropyrano[3,2-b]pyran-3-ol	909544-92-9	C₃₈H₄₅ClO₈	665.223
——	(2S,3S,4aR,8S,8aR,2'R,4'aS,6'R,7'S,8'S,8'aS)-7',8'-Bis-benzyloxy-6'-benzyloxymethyl-8-chloro-hexadecahydro-[2,2']bi[pyrano[3,2-b]pyranyl]-3-ol	909544-91-8	C₃₈H₄₅ClO₈	665.223
——	(2-O-benzoyl-4,6-O-benzylidene-3-O-[(S)-1-(oxycarbonyl)-2-cyclohexylethyloxy]-β-D-galactopyranosyl-O-(1->3)-[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-O-(1->4)]-6-O-benzyl-1,2-dideoxy-D-glucopyranose	438216-19-4	C₆₉H₇₈O₁₆	1163.37
——	(2-O-benzoyl-4,6-O-benzylidene-3-O-[(S)-1-(methoxycarbonyl)-2-cyclohexylethyloxy]-β-D-galactopyranosyl-O-(1->3)-[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-O-(1->4)]-6-O-benzyl-1,2-dideoxy-D-glucopyranose	438216-18-3	C₇₀H₈₀O₁₆	1177.4
——	(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-O-(1->4)-3-O-benzoyl-6-O-benzyl-1,2,-dideoxy-D-glucopyranose	438216-16-1	C₄₇H₅₀O₉	758.909
——	benzyl (2S)-3-cyclohexyl-2-[(2R,3S,4S,5R,6R)-3,5-dihydroxy-2-(hydroxymethyl)-6-[(2R,3S,4R)-3-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-2-(phenylmethoxymethyl)oxan-4-yl]oxyoxan-4-yl]oxypropanoate	252896-26-7	C₆₂H₇₆O₁₅	1061.28
——	[(2R,3S,4R)-4-(2-methoxyphenoxy)-3-phenylmethoxyoxan-2-yl]methanol	291273-53-5	C₂₀H₂₄O₅	344.408
——	[4-Methoxy-3-((2R,4aR,8R,8aS)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-phenyl]-phenyl-methanone	334022-45-6	C₂₇H₂₆O₆	446.5
——	(2S,3R,4aR,8S,8aR)-2-[(2R,3S,4S,4aS,6R,8aS)-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-2,3,4,4a,6,7,8,8a-octahydropyrano[3,2-b]pyran-6-yl]-8-chloro-4,4a,6,7,8,8a-hexahydro-3H-pyrano[3,2-b]pyran-2,3-diol	909544-90-7	C₃₈H₄₅ClO₉	681.223
——	(2S,3S,4aR,8S,8aR)-2-[(2R,3S,4S,4aS,6R,8aS)-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-2,3,4,4a,6,7,8,8a-octahydropyrano[3,2-b]pyran-6-yl]-8-chloro-4,4a,6,7,8,8a-hexahydro-3H-pyrano[3,2-b]pyran-2,3-diol	909544-89-4	C₃₈H₄₅ClO₉	681.223

反应信息

作为反应物：

描述：

1,5-Anhydro-2-deoxy-4,6-O-(phenylmethylene)-D-arabino-hexopyranoside 在草酰氯、 L-Selectride 、二甲基亚砜、三乙胺作用下，以四氢呋喃、二氯甲烷为溶剂，生成 1,5-anhydro-2-deoxy-4,6-O-benzylidene-D-ribohexitol

参考文献：

名称：

实用的手性配体合成方法，用于酮的催化对映选择性氰基硅烷化

摘要：

描述了可用于酮的催化对映选择性氰基硅烷化的手性配体的实用且对环境更有益的合成途径。关键步骤是与邻苯二酚衍生物对环硫酸盐12的区域选择性S N 2反应。通过这种新途径，可以得到一系列包含电子调节的邻苯二酚的手性配体。

DOI：

10.1016/s0040-4039(02)00450-1
作为产物：

描述：

3,4,6-tri-O-acetyl-1,2-dideoxy-D-glucopyranose 在甲醇、 sodium methylate 作用下，生成 1,5-Anhydro-2-deoxy-4,6-O-(phenylmethylene)-D-arabino-hexopyranoside

参考文献：

名称：

Foster et al., Acta Chemica Scandinavica (1947), 1958, vol. 12, p. 1819,1823

摘要：

DOI：

点击查看最新优质反应信息

文献信息

Catalytic enantioselective cyanosilylation of ketones: improvement of enantioselectivity and catalyst turn-over by ligand tuning

作者：Yoshitaka Hamashima、Motomu Kanai、Masakatsu Shibasaki

DOI：10.1016/s0040-4039(00)02039-6

日期：2001.1

the bifunctional catalyst 1 afforded the improved catalyst 2, which promoted the cyanosilylation of ketones with higher enantioselectivity as well as with improved catalyst turn-over with a factor of up to 10. Thus, chiral quaternary α-hydroxynitriles were obtained with excellent ee (up to 94% ee) using 1 mol% of 2 in the case of aryl ketones and 2.5 mol% of 2 in the case of aliphatic ketones.

对双官能催化剂1进行立体和电子调谐，得到了改进的催化剂2，该催化剂以较高的对映选择性和最大为10的改进的催化剂周转率促进了酮的氰基甲硅烷基化反应。在芳基酮的情况下使用1 mol％的2和在脂族酮的情况下使用2.5 mol％的2时，具有优异的ee（最高94％ee）。
Highly Stereoselective [3+2] Cycloadditions of Nitrile Oxides to Methyl 4-O-Acryloyl-6-deoxy-2,3-O-(t-butyldimethylsilyl)-α-<scp>d</scp>-glucopyranoside

作者：Kin-ichi Tadano、Tetsuo Tamai、Shingo Asano、Kiichiro Totani、Ken-ichi Takao

DOI：10.1055/s-2003-41404

日期：——

The [3+2] cycloadditions of benzonitrile oxide or pivalonitrile oxide to methyl 4-O-acryloyl-6-deoxy-2,3-di-O-(t-butyldimethylsilyl)-Î±-d-glucopyranoside provided the respective adducts, each as virtually a single diastereomer. By reductive removal of the carbohydrate template from each adduct, the respective (R)-enriched Î2-isoxazoline derivative was obtained.

苯甲腈氧化物或三甲基乙腈氧化物与甲基4-O-丙烯酰基-6-脱氧-2,3-二-O-(叔丁基二甲基硅基)-α-d-葡糖吡喃糖苷的[3+2]环加成反应，分别得到近乎单一的非对映异构体的加合物。通过还原性去除每个加合物中的碳水化合物模板，分别获得了富集(R)构型的Δ2-异恶唑啉衍生物。
Solution and Solid-Phase Stereocontrolled Synthesis of 1,2-cis-Glycopyranosides with Minimally Protected Glycopyranosyl Donors Catalyzed by BF3–N,N-Dimethylformamide Complex

作者：Gabrielle St-Pierre、Stephen Hanessian

DOI：10.1021/acs.orglett.6b01263

日期：2016.7.1

Methods are described for the stereoselective synthesis of 1,2-cis glycopyranosides in the d-galacto, d-gluco, and 2-azido-2-deoxy-d-glucopyranoside series utilizing minimally protected (3-bromo-2-pyridyloxy) β-d-glycopyranosyl donors in the presence of BF3–N,N-dimethylformamide (DMF) as a catalyst and a variety of alcohol acceptors relying on the “remote activation concept”. Precursors to antifreeze

方法的1,2-立体选择性合成中描述的顺式glycopyranosides在d半乳，d -gluco和2-叠氮基-2-脱氧d吡喃葡萄糖苷系列利用所最低限度地受保护的（3-溴-2-吡啶基氧基）β - d在BF的存在-glycopyranosyl供体3 - ñ，ñ-二甲基甲酰胺（DMF）作为催化剂和多种醇受体，依赖于“远程活化概念”。抗冻糖肽组分的前体以优异的产率和高的α/β比率合成。该方法适用于一锅顺序糖苷化反应以及固相支持的合成方法，从而可以得到各种主要保护的最低限度保护的α- d-吡喃葡萄糖苷类化合物。
Method of producing oxybutynin and its derivatives

申请人：THE UNIVERSITY OF TOKYO

公开号：US20040006243A1

公开（公告）日：2004-01-08

An oxybutynin and its derivatives are produced by reacting a phenylketone with a silylcyanide in the presence of a specified asymmetric catalyst to obtain a siloxynitrile, and then reacting the siloxynitrile with a reducing agent and oxidizing the resulting aldehyde, or subjecting the siloxynitrile to a hydrolysis.

通过在指定的不对称催化剂存在下，将苯基酮与硅氰化物反应，制得硅氧腈，然后将硅氧腈与还原剂反应并氧化所得的醛，或者将硅氧腈进行水解，从而生产奥西布丁及其衍生物。
Simplified Sialyl Lewisx Analogues with Improved E-Selectin Inhibition

作者：Gebhard Thoma、Franz Schwarzenbach

DOI：10.1002/hlca.200390085

日期：2003.3

simplified sialyl Lewisx mimic 5 containing a D-arabinose, a 3-cyclohexyl-2-hydroxypropanoate, and a tetrahydropyran building block instead of L-fucose, sialic acid, and N-acetylglucosamine, respectively was synthesized. Compound 5 was 10-fold more potent than sLex in a static E-selectin binding assay and showed at 50 μM 75% inhibition in a dynamic-flow assay in which sLex did not inhibit neutrophil

合成了分别包含D-阿拉伯糖，3-环己基-2-羟基丙酸酯和四氢吡喃结构单元而不是L-岩藻糖，唾液酸和N-乙酰基葡糖胺的简化的唾液酸化的Lewis x mimic 5。在静态E-选择素结合测定中，化合物5的效力比sLe x高10倍，在动态流量测定中，sLe x在最高1000μM时不抑制嗜中性粒细胞滚动，在动态流量测定中显示50％抑制75％。与sLe x相比，具有乳酸而不是唾液酸结构单元的化合物7的效能提高了三倍。

同类化合物