2,3,4,6-四-O-苄基-D-吡喃半乳糖三氯乙亚氨酸酯 | 132748-02-8

分子结构分类

有机化合物 - 有机氧化合物

中文名称

2,3,4,6-四-O-苄基-D-吡喃半乳糖三氯乙亚氨酸酯

中文别名

2,3,4-四-O-苄基-D-半乳糖苷

英文名称

O-(2,3,4,6-tetra-O-benzyl-α,β-D-galactopyranosyl)trichloroacetimidate

英文别名

2,3,4,6-tetra-O-benzyl-D-galactopyranosyl-trichloroacetimidate；galactosyl trichloroacetimidate；O-(2,3,4,6-tetra-O-benzyl-D-galactopyranosyl) trichloroacetimidate；2,3,4,6-tetra-O-benzyl-D-galactosyl trichloroacetimidate；2,3,4,6-tetra-O-benzyl-D-galactopyranosyl trichloroacetoimidate；2,3,4,6-Tetra-O-benzyl-D-galactopyranose trichloroacetimidate；[(3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl] 2,2,2-trichloroethanimidate

CAS

132748-02-8

化学式

C₃₆H₃₆Cl₃NO₆

mdl

——

分子量

685.044

InChiKey

LMICALCPRSCSMO-BJPULKCASA-N

BEILSTEIN

——

EINECS

——

物化性质

熔点：

78-79°C
溶解度：

可溶于丙酮、氯仿、DMSO、甲醇

计算性质

辛醇/水分配系数(LogP)：

7.5
重原子数：

46
可旋转键数：

15
环数：

5.0
sp3杂化的碳原子比例：

0.31
拓扑面积：

79.2
氢给体数：

1
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
2,3,4,6-四-O-苄基-D-吡喃半乳糖	2,3,4,6-tetra-O-benzyl-D-galactopyranose	6386-24-9	C₃₄H₃₆O₆	540.656
4-甲氧苯基-2,3,4,6-四-O-苄基-Β-D-吡喃半乳糖苷	p-methoxyphenyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranoside	143536-99-6	C₄₁H₄₂O₇	646.78

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	methyl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-α-D-glucopyranoside	——	C₆₂H₆₆O₁₁	987.199
——	methyl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-α-D-glucopyranoside	——	C₆₂H₆₆O₁₁	987.199
——	cyclohexyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranoside	——	C₄₀H₄₆O₆	622.802
——	cyclohexyl 2,3,4,6-tetra-O-benzyl-α-D-galactopyranoside	——	C₄₀H₄₆O₆	622.802
——	methyl 2,3,4,6-tetra-O-benzyl α-D-galactopyranoside	3879-79-6	C₃₅H₃₈O₆	554.683
甲基-2,3,4,6-四-O-苄基-Alpha-D-吡喃半乳糖苷	methyl 2,3,4,6-tetra-O-benzyl-α-D-galactopyranoside	53008-63-2	C₃₅H₃₈O₆	554.683
——	2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose	——	C₄₆H₅₄O₁₁	782.928
——	(2S,3S,4R,5Z)-2-azido-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)-3,4-dibenzyloxy-5-octadecene	877380-45-5	C₆₆H₈₁N₃O₈	1044.38
——	D-galactopyranosyl-α-(1->2)-D-chiro-inositol	79391-04-1	C₁₂H₂₂O₁₁	342.3
1,3-二羟基-2-丙基alpha-D-吡喃半乳糖苷	(2S,3R,4S,5R,6R)-2-(2-Hydroxy-1-hydroxymethyl-ethoxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol	534-68-9	C₉H₁₈O₈	254.237

反应信息

作为反应物：

描述：

2,3,4,6-四-O-苄基-D-吡喃半乳糖三氯乙亚氨酸酯在 palladium on activated charcoal 三氟甲磺酸三甲基硅酯、 4 A molecular sieve 、氢气、 sodium methylate 作用下，以四氢呋喃、甲醇、乙醚、乙醇、水为溶剂，反应 1.5h，生成 D-galactopyranosyl-α-(1->2)-D-chiro-inositol

参考文献：

名称：

Synthesis of fagopyritols A1 and B1 from d-chiro-inositol

摘要：

Fagopyritol Al (3-O-alpha-D-galactopyranosyl-D-chiro-inositol) and fagopyritol B1 (2-O-alpha-D-galactopyranosyl-D-chiro-inositol) have been synthesized by glycosylation of the diequatorial diol 1,4,5,6-tetra-O-benzoyl-D-chiro-inositol, readily obtained from D-chiro-inositol, with 2,3,4,6-tetra-O-benzyl-D-galactopyranosyl trichloroacetimidate. (C) 2004 Elsevier Ltd. All rights reserved.

DOI：

10.1016/j.carres.2004.06.021
作为产物：

描述：

4-甲氧基苯基-Β-D-半乳糖苷在 ammonium cerium(IV) nitrate 、 sodium hydride 作用下，以水、 N,N-二甲基甲酰胺、甲苯、乙腈为溶剂，反应 2.83h，生成 2,3,4,6-四-O-苄基-D-吡喃半乳糖三氯乙亚氨酸酯

参考文献：

名称：

Total Synthesis of Floridoside

摘要：

从红色海洋藻掌红藻 (Rhodymenia palmata) 中分离出的天然佛罗里达苷 [2′-O-(α-d-吡喃半乳糖基)-甘油] 已显示出有效的免疫刺激活性。为了进行进一步的生物学研究，该化合物的合成似乎是必要的，并且在此首次报道。

DOI：

10.1055/s-2007-984499

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文献信息

Design and synthesis of inositolphosphoglycan putative insulin mediators

作者：Javier López-Prados、Félix Cuevas、Niels-Christian Reichardt、José-Luis de Paz、Ezequiel Q. Morales、Manuel Martín-Lomas

DOI：10.1039/b418041k

日期：——

results from the biological evaluation of these molecules provide additional support to an insulin-mediated signalling system which involves the intermediacy of inositolphosphoglycans as putative insulin mediators.

使用分子对接分析了一系列包含葡糖胺（1→6）肌醇结构基序的分子与cAMP依赖性蛋白激酶（PKA）催化亚基的ATP结合位点的结合模式。这些计算预测假二糖和假三糖结构中非还原端的磷酸基团的存在将分子正确地定向到结合位点，并且假三糖结构呈现出最佳的形状互补性。因此，已经使用有效的合成策略从常见的中间体合成了伪二糖和伪三糖。基于这种合成化学，已经探索了使用相同的中间体在固相上构建小的假三糖文库的可行性。
Fluorine-Directed β-Galactosylation: Chemical Glycosylation Development by Molecular Editing

作者：Estelle Durantie、Christoph Bucher、Ryan Gilmour

DOI：10.1002/chem.201200468

日期：2012.6.25

Validation of the 2‐fluoro substituent as an inert steering group to control chemical glycosylation is presented. A molecular editing study has revealed that the exceptional levels of diastereocontrol in glycosylation processes by using 2‐fluoro‐3,4,6‐tri‐O‐benzyl glucopyranosyl trichloroacetimidate (TCA) scaffolds are a consequence of the 2R,3S,4S stereotriad. This study has also revealed that epimerization

提出了将2-氟取代基作为控制化学糖基化反应的惰性指导基团的验证方法。一项分子编辑研究表明，通过使用2-氟-3,4,6-三-O-苄基吡喃葡萄糖基三氯乙酰亚氨酸酯（TCA）支架，糖基化过程中非对映异构控制的异常水平是2 R，3 S，4的结果S立体三合会。这项研究还表明，C4的差向异构作用会导致β选择性大大提高（高达β/α300：1）。
Synthetic avenues towards a tetrasaccharide related to Streptococcus pneumonia of serotype 6A

作者：Aritra Chaudhury、Mana Mohan Mukherjee、Rina Ghosh

DOI：10.3762/bjoc.14.95

日期：——

Streptococcus pneumonia (SPn) is a Gram-positive bacterium which causes life threatening diseases. The bacteria protect themselves against non-specific host defence by an external polysaccharide (PS) capsule which bears a repeating unit, α-D-Galp(1->3)-α-D-Glcp(1->3)-α-L-Rhap(1->3)-D-Rib (SPn 6A). A closer look at the structure reveals the presence of α-linked galactose and glucose residues. The synthesis of these 1,2-cis glycosidic linkages are considered challenging particularly in the context of a one-pot oligosaccharide synthesis. We have synthesized the aforesaid tetrasaccharide (SPn 6A) based on both stepwise and sequential one-pot glycosylation reactions using easily accessible common building blocks; eventually similar overall yields were obtained in both cases.

肺炎链球菌（SPn）是一种革兰氏阳性细菌，能引起威胁生命的疾病。这些细菌通过一种外部多糖（PS）胶囊来保护自己，免受宿主非特异性防御，这种胶囊带有重复单元，α-D-Galp(1->3)-α-D-Glcp(1->3)-α-L-Rhap(1->3)-D-Rib（SPn 6A）。仔细观察其结构可以发现α连接的半乳糖和葡萄糖残基的存在。这些1,2-cis糖苷键的合成被认为是具有挑战性的，特别是在一锅寡糖合成的情况下。我们已经合成了上述的四糖（SPn 6A），基于逐步和顺序的一锅糖基化反应，使用易于获取的常见构建模块；最终在这两种情况下获得了相似的总收率。
Sweet (hetero)aromatics: glycosylated templates for the construction of saccharide mimetics

作者：Christine Wiebe、Claudine Schlemmer、Stefan Weck、Till Opatz

DOI：10.1039/c1cc13078a

日期：——

Mono- and diglycosylated aromatics and heteroaromatics may serve as building blocks for the construction of metabolically stable mimetics of oligosaccharides. Methods for their preparation from monosaccharidic precursors by direct C-glycosylation, dipolar cycloaddition or Larock cyclization are described.

单糖基和二糖基修饰的芳香化合物和杂芳香化合物可作为构建代谢稳定的低聚糖模拟物的砌块。本文描述了通过直接C-糖基化、偶极环加成或Larock环化反应从单糖前体合成这些化合物的方法。
Synthese eines 1,2-trans-konfigurierten, äquatorialen Glycosyl-phosphonat-Analogen von<scp>D</scp>-myo-Inositol-1,4,5-trisphosphat

作者：LáSzló Czollner、Gisèle Baudin、Bruno Bernet、Andrea Vasella

DOI：10.1002/hlca.19930760224

日期：1993.3.24

Synthesis of a 1,2-trans-Configurated, Equatorial Glycosylphosphonate Analogue of D-myo-Inositol 1,4,5-Trisphosphate

1,2-合成反式-构型，赤道Glycosylphosphonate D-的模拟肌1,4,5-三磷酸肌醇