para-methoxyphenyl-4,6-O-benzylidene-1-O-β-D-galactopyranoside | 1269657-95-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: para-methoxyphenyl-4,6-O-benzylidene-1-O-β-D-galactopyranoside
• 英文别名: (2R,4aR,6S,7R,8R,8aR)-6-(4-methoxyphenoxy)-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol
• CAS: 1269657-95-5
• 化学式: C₂₀H₂₂O₇
• 分子量: 374.39
• InChiKey: YHRLBNMWLPNUFF-IGOIZDSHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  86.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  para-methoxyphenyl-4,6-O-benzylidene-1-O-β-D-galactopyranoside 在 吡啶 、 三乙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 22.5h， 生成 para-methoxyphenyl-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosyl)-(1→4)-2',3'-di-O-acetyl-6'-O-benzyl-1'-O-β-D-galactopyranoside
  参考文献：
  名称：

  二糖苷四甲酸安克龙苷A的全合成

  摘要：

  甜酸：以第18步合成海洋海绵代谢产物ancorinoside A，其收率为1.6％，是第一个天然的二糖基化吡咯烷-2,4-二酮。显着地，它由d-构型的天冬氨酸，半乳糖醛酸和3-酰基四甲酸组成。

  DOI：

  10.1002/chem.201704379
• 作为产物：
  描述：

  4-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 在 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 1.25h， 生成 para-methoxyphenyl-4,6-O-benzylidene-1-O-β-D-galactopyranoside
  参考文献：
  名称：

  二糖苷四甲酸安克龙苷A的全合成

  摘要：

  甜酸：以第18步合成海洋海绵代谢产物ancorinoside A，其收率为1.6％，是第一个天然的二糖基化吡咯烷-2,4-二酮。显着地，它由d-构型的天冬氨酸，半乳糖醛酸和3-酰基四甲酸组成。

  DOI：

  10.1002/chem.201704379

文献信息

• Multiple and Regioselective Introduction of Protected Sulfates into Carbohydrates Using Sulfuryl Imidazolium Salts
  作者：Ahmed Y. Desoky、Scott D. Taylor

  DOI：10.1021/jo901882f

  日期：2009.12.18

  Selective incorporation of trichloroethyl (TCE)-protected sulfates into monosaccharides was examined using reagent 2. In general, sulfation of 4,6-O-benzylidene acetals of galactosides and glucosides (2-OH versus 3-OH sulfations) proceeded in good to excellent yield and selectivity. Sulfation occurred predominantly at the 2-OH in 4,6-O-benzylidene acetals of α-glucosides and at the 3-OH in 4,6-O-benzylidene

  使用试剂2检查了三氯乙基（TCE）保护的硫酸盐到单糖中的选择性掺入。通常，半乳糖苷和葡糖苷的4，6- O-亚苄基乙缩醛的硫酸化（2-OH对3-OH的硫酸化）以良好的收率和优异的选择性进行。硫酸化主要发生在α-葡萄糖苷的4,6- O-亚苄基乙缩醛中的2-OH和β-半乳糖苷和β-葡萄糖苷的4,6- O-亚苄基乙缩醛中的3-OH 。在糖苷和半乳糖苷的3,4-二醇中的3-OH也获得了良好的收率和选择性。带有2-氨基部分和6-OH基团的葡糖苷主要产生N-硫酸化产物，产率高。通常还可以良好的收率和选择性实现在带有一个或两个自由仲羟基的半乳糖和葡萄糖衍生物中伯6-羟基的选择性硫酸化。试剂2对于糖苷和半乳糖苷的二醇的直接脱硫也是有效的，并且可以从脱硫的化合物制备三硫酸化的单糖。
• Preparation of trifluoroethyl- and phenyl-protected sulfates using sulfuryl imidazolium salts
  作者：Ahmed Y. Desoky、Jennifer Hendel、Laura Ingram、Scott Douglas Taylor

  DOI：10.1016/j.tet.2010.11.085

  日期：2011.2

  Sulfuryl imidazolium salts (SIS's), a new class of sulfating agents, were prepared bearing the trifluoroethyl (TFE) and phenyl groups, two functionalities that have been used for the protection of sulfate monoesters, by subjecting the corresponding sulfonyl imidazoles with methyl triflate. In contrast, SIS's bearing the electron donating neopentyl and isobutyl groups, two moieties that have also been used for the protection of sulfates, were found to be unstable and could not be isolated though SIS's bearing electron donating aryl groups, such as a p-methoxyphenyl or p-thiomethylphenyl group were readily prepared and are stable compounds. In most instances, TFE-protected phenolic and carbohydrate sulfates were obtained in good yield by reaction of the corresponding SIS's with steroids and carbohydrates. Phenyl-protected carbohydrates were also readily prepared using the corresponding SIS's. Those SIS's having a methyl group at the 2-position of the imidazole ring were, in general, superior sulfating agents to those, which lacked a methyl group at this position. The use of SIS's to prepare TFE-protected sulfates represents a significant improvement of the previous reported procedure, which involved treating unprotected sulfates with trifluorodiazoethane. The TFE protecting group was removed from steroidal sulfates and secondary sulfates in carbohydrates in high yields using NaN(3) in warm DMF, conditions that are less vigorous than those previously reported for removing this group. Deprotection of TFE-protected 6-sulfated carbohydrates using NaN3 in warm DMF proceeded in lower yields due to partial desulfation. (C) 2010 Elsevier Ltd. All rights reserved.
• FeCl3 mediated arylidenation of carbohydrates
  作者：Nabamita Basu、Sajal K. Maity、Soumik Roy、Shuvendu Singha、Rina Ghosh

  DOI：10.1016/j.carres.2011.01.003

  日期：2011.4

  Glycosides and thioglycosides based on monosaccharides in reaction with benzaldehyde dimethylacetal or p-methoxybenzaldehyde dimethyl acetal undergo FeCl3-catalyzed (20 mol %) regioselective 4,6-0-arylidenation producing the corresponding acetals in high yields. FeCl3 also mediates acetalation of glycosides and thioglycosides of cellobiose, maltose, and lactose affording the corresponding 4',6'-O-benzylidene acetals, which were isolated after their acetylation in situ with acetic anhydride and pyridine. The combined yields (two steps) of these final products are also high (61-84%). The procedure is applicable to a wide variety of functional groups including -OBn. (C) 2011 Elsevier Ltd. All rights reserved.