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1,2:5,6-di-O-isopropylidene-3-O-trifluoromethanesulfonyl-α-D-allofuranose | 55951-90-1

分子结构分类

有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物

中文名称

——

中文别名

——

英文名称

1,2:5,6-di-O-isopropylidene-3-O-trifluoromethanesulfonyl-α-D-allofuranose

英文别名

(3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydro-2H-furo[2,3-d][1,3]dioxol-6-yl trifluoromethanesulfonate；1,2:5,6-di-O-isopropylidene-3-O-trifluoromethanesulphonyl-α-D-allofuranose；3-O-trifluoromethanesulfonyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose；1,2:5,6-di-O-isopropylidene-3-trifluoromethanesulfonyl-α-D-allofuranose；1,2:5,6-di-O-isopropylidene-3-O-triflyl-α-D-allofuranose；1,2;5,6-di-O-isopropylidene-3-O-trifyl-D-allofuranose；1-O,2-O:5-O,6-O-Diisopropylidene-alpha-D-allofuranose 3-trifluoromethanesulfonate；[(3aR,5R,6R,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] trifluoromethanesulfonate

1,2:5,6-di-O-isopropylidene-3-O-trifluoromethanesulfonyl-α-D-allofuranose化学式

CAS

55951-90-1

化学式

C₁₃H₁₉F₃O₈S

mdl

——

分子量

392.35

InChiKey

VVOYXQBDMGGDJZ-VVULQXIFSA-N

BEILSTEIN

——

EINECS

——

物化性质

沸点：

385.1±42.0 °C(Predicted)
密度：

1.49±0.1 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

1.3
重原子数：

25
可旋转键数：

3
环数：

3.0
sp3杂化的碳原子比例：

1.0
拓扑面积：

97.9
氢给体数：

0
氢受体数：

11

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
1,2:5,6-二异亚丙基-alpha-D-异呋喃糖	Diacetone D-glucose	2595-05-3	C₁₂H₂₀O₆	260.287
双丙酮葡萄糖	1,2:5,6-di-O-isopropylidene-α-D-glucofuranose	582-52-5	C₁₂H₂₀O₆	260.287
二丙酮-D-葡萄糖	(1,2:5,6)-di-O-isopropylidene-D-gulose	14686-89-6	C₁₂H₂₀O₆	260.287
1,2:5,6-二-o-异亚丙基-alpha-d-ribo-3-己呋喃核糖	1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose	2847-00-9	C₁₂H₁₈O₆	258.271

下游产品

中文名称	英文名称	CAS号	化学式	分子量
二丙酮-D-葡萄糖	(1,2:5,6)-di-O-isopropylidene-D-gulose	14686-89-6	C₁₂H₂₀O₆	260.287
——	1,2:5,6-di-O-isopropylidene-α-D-galactofuranose	10368-86-2	C₁₂H₂₀O₆	260.287
——	3-deoxy-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside	4613-62-1	C₁₂H₂₀O₅	244.288
——	3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1-3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose	64694-26-4	C₄₆H₅₄O₁₁	782.928
——	(3aR,5R,6S,6aR)-6-(2-bromophenoxy)-5-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole	1356036-79-7	C₁₈H₂₃BrO₆	415.281
——	3-deoxy-1,2;5,6-di-O-isopropylidene-3-fluoro-α-D-glucofuranose	14049-05-9	C₁₂H₁₉FO₅	262.278
——	1,2:5,6-di-O-isopropylidene-3-deoxy-3-thio-α-D-glucofuranose	54497-88-0	C₁₂H₂₀O₅S	276.354
——	methyl 3-O-(1,2:5,6-di-O-isopropylidene-3-deoxy-α-D-glucofuranos-3-yl)-4,6-O-benzylidene-2-O-benzyl-β-D-glucopyranoside	1227925-49-6	C₃₃H₄₂O₁₁	614.69
——	methyl 3-O-(1,2:5,6-di-O-isopropylidene-3-deoxy-α-D-glucofuranos-3-yl)-4,6-O-benzylidene-2-O-benzyl-α-D-glucopyranoside	1227925-48-5	C₃₃H₄₂O₁₁	614.69
——	3-Brom-3-desoxy-1,2;5,6,-di-O-isopropyliden-α-D-glucofuranose	14260-29-8	C₁₂H₁₉BrO₅	323.184
——	3-deoxy-3-fluoro-1,2-O-isopropylidene-α-D-glucofuranose	18530-81-9	C₉H₁₅FO₅	222.214
——	Trifluoro-methanesulfonic acid 4(R)-azido-5(S)-(2,2-dimethyl-[1,3]dioxolan-4(R)-yl)-2-oxo-tetrahydro-furan-3(R)-yl ester	308806-97-5	C₁₀H₁₂F₃N₃O₇S	375.282
——	(3aR,5R,6S,6aS)-6-[[(3aR,5R,6S,6aS)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl]selanyl]-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole	1221269-58-4	C₂₄H₃₈O₁₀Se	565.52
——	3-amino-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose	——	C₁₂H₂₁NO₅	259.302
——	3-Se-benzoyl-3-deoxy-1,2:5,6-di-O-isopropylidene-3-seleno-α-D-glucofuranose	1221269-53-9	C₁₉H₂₄O₆Se	427.356

反应信息

作为反应物：

描述：

1,2:5,6-di-O-isopropylidene-3-O-trifluoromethanesulfonyl-α-D-allofuranose 在 sodium tetrahydroborate 作用下，以乙腈为溶剂，反应 72.0h，生成 3-deoxy-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside

参考文献：

名称：

Novel 4′-Branched Nucleosides

摘要：

Total chemical synthesis of 4'-hydroxymethylnucleosides with an additional modification in a sugar residue was developed. The synthesis was made by condensation of corresponding protected sugars and nucleic bases with subsequent deprotection. In such a way 3'-azido- and 3'-amino-3'deoxy-4'-hydroxymethylribonucleosides, 2',3'-anhydroribo- and 2',3'-anhydrolyxo-4'-hydroxymethylribonucleosides as well as 3'-deoxy-4'hydroxymethylribollucleosides were prepared. At concentrations up to 100 mu M none of them inhibited reproduction of human immunodeficiency virus type 1 in H9 and PBL cells as well as human herpes simplex virus type 2 and human cytomegalovirus in vero cells.

DOI：

10.1080/15257779408013221
作为产物：

描述：

D-葡萄糖在吡啶、 sodium tetrahydroborate 、重铬酸吡啶、磷酸、乙酸酐、 zinc(II) chloride 作用下，以乙醇、二氯甲烷、水为溶剂，反应 41.75h，生成 1,2:5,6-di-O-isopropylidene-3-O-trifluoromethanesulfonyl-α-D-allofuranose

参考文献：

名称：

Kanosamine 生物合成：Aminoshikimate 途径的氮原子的可能来源

摘要：

掺入氨基莽草酸酯途径的氮原子的生物合成来源一直是一个问题。3-氨基-3-脱氧-D-果糖 6-磷酸先前已被证明是 4-氨基-3,4-二脱氧-D-阿拉伯-庚糖酸 7-磷酸和 3-氨基-5-羟基苯甲酸的前体通过推断的 1-deoxy-1-imino-D-erythrose 4-phosphate 中间体在 Amycolatopsis mediterranei 无细胞提取物中产生酸。这项调查研究了天然产物卡诺胺可能是 3-amino-3-deoxy-D-fructose 6-phosphate 的前体的可能性。卡诺胺 6-磷酸是通过化学酶促途径合成的，并与 D-核糖 5-磷酸和磷酸烯醇丙酮酸一起在无细胞裂解物中孵育。4-氨基-3的形成，观察到4-双脱氧-D-阿拉伯-庚酮糖酸7-磷酸和3-氨基-5-羟基苯甲酸。随后在 A. mediterranei 的无细胞裂解物中孵育谷氨酰胺和 NAD 与 UDP

DOI：

10.1021/ja026628m

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文献信息

[EN] COMPOSITIONS AND METHODS FOR THE TREATMENT OF BACTERIAL INFECTIONS<br/>[FR] COMPOSÉS ET MÉTHODES POUR LE TRAITEMENT D'INFECTIONS BACTÉRIENNES

申请人：CIDARA THERAPEUTICS INC

公开号：WO2018006063A1

公开（公告）日：2018-01-04

Compositions and methods for the treatment of bacterial infections include compounds containing dimers of cyclic heptapeptides conjugated to one or more monosaccharide or oligosaccharide moieties. In particular, compounds can be used in the treatment of bacterial infections caused by Gram-negative bacteria.

用于治疗细菌感染的组合物和方法包括含有环七肽二聚体与一个或多个单糖或寡糖基团结合的化合物。特别是，这些化合物可用于治疗由革兰氏阴性细菌引起的细菌感染。
Synthesis of carbasugar-containing non-glycosidically linked pseudodisaccharides and higher pseudooligosaccharides

作者：Ian Cumpstey

DOI：10.1016/j.carres.2009.09.008

日期：2009.11

This minireview covers synthetic methods towards carbasugar-containing non-glycosidically linked pseudodisaccharides or higher pseudooligosaccharides. Carbocyclic pyranose mimetics (saturated or unsaturated between C-5 and C-5a) are linked by ether, thioether or amine bridges to carbohydrates or other carbasugars.

这份简短的综述涵盖了针对含碳水化合物的非糖苷键连接的假二糖或高级假寡糖的合成方法。碳环吡喃糖模拟物（在C-5和C-5a之间饱和或不饱和）通过醚桥，硫醚桥或胺桥连接到碳水化合物或其他Carcarbugars。
Synthesis, photophysical properties, and photodynamic activity of positional isomers of TFPP-glucose conjugates

作者：Arif Fadlan、Hiroki Tanimoto、Tatsuya Ito、Yusuke Aritomi、Maho Ueno、Masaya Tokuda、Shiho Hirohara、Makoto Obata、Tsumoru Morimoto、Kiyomi Kakiuchi

DOI：10.1016/j.bmc.2018.02.031

日期：2018.5

The synthesis and characterization of a ‘complete set’ of positional isomers of tetrakis(perfluorophenyl)porphyrins (TFPP)-glucose conjugates (1OH, 2OH, 3OH, 4OH, and 6OH) are reported herein. The cellular uptake and photocytotoxicity of these conjugates were examined in order to investigate the influence of location of the TFPP moiety on the d-glucose molecule on the biological activity of the conjugates

本文报道了四（全氟苯基）卟啉（TFPP）-葡萄糖缀合物（1OH，2OH，3OH，4OH和6OH）的位置异构体的“完整集”的合成和表征。为了研究TFPP部分在d-葡萄糖分子上的位置对缀合物的生物学活性的影响，检查了这些缀合物的细胞摄取和光细胞毒性。一种在体外生物评价，结果这些特定的异构体对细胞摄取和细胞毒性比别人更大的影响。TFPP-葡萄糖结合物1OH，3OH和与2OH和6OH取代的异构体相比，发现4OH在几种类型的癌细胞中具有优异的光细胞毒性。
The rapid synthesis of deoxyfluoro sugars using tris(dimethylamino)sulfonium difluorotrimethylsilicate (TASF)

作者：Bogdan Doboszewski、George W. Hay、Walter A. Szarek

DOI：10.1139/v87-070

日期：1987.2.1

Deoxyfluoro sugars were synthesized rapidly by the reaction of trifluoromethanesulfonyl derivatives of partially protected sugars with tris(dimethylamino)sulfonium difluorotrimethylsilicate (TASF) under mild conditions. The displacements occurred with inversion of configuration; fluorine has been introduced stereospecifically at each of the secondary alcoholic sites of aldohexopyranosides and in one

脱氧氟糖是通过部分保护糖的三氟甲磺酰基衍生物与三（二甲氨基）锍二氟三甲基硅酸盐（TASF）在温和条件下反应快速合成的。位移发生于构型反转；在吡喃醛糖苷的每个二级醇位点和呋喃类系统的一个例子中，氟已被立体定向地引入。在某些情况下，会产生不含氟的不饱和化合物。
α-Hydrogen elimination in some carbohydrate triflates

作者：Ahmed El Nemr、Tsutomu Tsuchiya

DOI：10.1016/0040-4039(95)01607-j

日期：1995.10

In some carbohydrate triflates, treatment with MeLi (or BuLi) in ether caused α-hydrogen elimination initially, then the resulting carbanion is stabilized to give either C-methyl(or butyl)-hydroxy derivatives or unsaturated products.

在一些碳水化合物三氟甲磺酸酯中，用乙醚中的MeLi（或BuLi）处理首先引起α-氢消除，然后将所得的碳负离子稳定化，得到C-甲基（或丁基）-羟基衍生物或不饱和产物。