allyl α-D-xylopyranoside | 140420-69-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl α-D-xylopyranoside
• 英文别名: (2S,3R,4S,5R)-2-prop-2-enoxyoxane-3,4,5-triol
• CAS: 140420-69-5
• 化学式: C₈H₁₄O₅
• 分子量: 190.196
• InChiKey: SQPCRAFFYUVIQE-CWKFCGSDSA-N

物化性质

• 熔点：
  98 °C(Solv: dichloromethane (75-09-2); methanol (67-56-1))
• 沸点：
  345.9±42.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  allyl α-D-xylopyranoside 在 水 、 sodium hydride 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 作用下， 以 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 生成 (2,3-dibenzyloxypropyl) 2,3,4-tri-O-benzyl-α-D-xylopyranoside
  参考文献：
  名称：

  Moitessier, Nicolas; Maigret, Bernard; Chretien, Francoise, European Journal of Organic Chemistry, 2000, # 6, p. 995 - 1005

  摘要：

  DOI：
• 作为产物：
  描述：

  allyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 allyl α-D-xylopyranoside
  参考文献：
  名称：

  Synthesis and biological activities of inositol 1,4,5-trisphosphate mimics related to xylopyranosides

  摘要：

  2', 3, 4-trisphosphates of (2-hydroxyethyl) alpha- and beta-D-xylopyranosides and 3', 3, 4-trisphosphates of (3-hydroxypropyl) alpha- and beta-D-xylopyranosides have been prepared from allyl-D-xylosides and showed agonistic properties toward inositol 1, 4, 5-trisphosphate receptor.

  DOI：

  10.1016/0040-4039(95)01677-a

文献信息

• Sulfonated graphene oxide as highly efficient catalyst for glycosylation
  作者：Raju S. Thombal、Vrushali H. Jadhav

  DOI：10.1080/07328303.2015.1120874

  日期：2016.1.2

  Heterogeneous sulfonated graphene oxide for the first time has been used as a green and efficient catalyst for atom-economic glycosylation of unprotected, unactivated glycosyl donors or 2,3,4,6-tetra-O-acetylglycosyltrichloroacetimidate with various acceptors basically in the absence of solvent. The unprotected, unactivated glycosyl donors afforded mixtures of α- and β-glycosides, while the 2,3,4,

  基本上，在不存在任何保护基的情况下，非均相磺化氧化石墨烯已被首次用作未受保护的，未活化的糖基供体或带有各种受体的2,3,4,6-四-O-乙酰基糖基三氯乙酰胺酸酯的原子经济糖基化的绿色高效催化剂。溶剂。未保护的，未活化的糖基供体提供了α-和β-糖苷的混合物，而2,3,4,6-四-O-乙酰基糖基三氯乙酰胺酸酯提供了高收率和高选择性的β-糖基化产物。这种方法的主要优点是易于制备催化剂，无需干燥试剂和反应条件，易于催化剂分离和再循环以及高产物收率。
• Synthesis of New Serine-Linked Oligosaccharides in Blood-Clotting Factors VII and IX and Protein Z.The Syntheses of<i>O</i>-α-D-Xylopyranosyl-(1→3)-D-glucopyranose,<i>O</i>-α-D-Xylopyranosyl-(1→3)-<i>O</i>-α-D-xylopyranosyl-(1→3)-D-glucopyranose, and Their Conjugates with Serine
  作者：Koichi Fukase、Sumihiro Hase、Tokuji Ikenaka、Shoichi Kusumoto

  DOI：10.1246/bcsj.65.436

  日期：1992.2

  prepared from 2,3,4-tri-O-benzyl-α-D-xylopyranosyl fluoride and allyl 2,4,6-tri-O-acetyl-α-D-grucopyranoside (9a) using tin(II) chloride and silver perchlorate as glycosylating reagents. The trisaccharide α-D-Xylp(1→3)-α-D-Xylp(1→3)-D-Glcp was prepared from O-(2,3,4-tri-O-benzyl-α-D-xylopyranosyl)-(1→3)-2,4-di-O-benzyl-α,β-D-xylopyranosyl fluoride and 9a with the same reagents. Their conjugates with

  为了阐明它们的生物学功能，合成了最近在牛和人凝血因子 VII、IX 和蛋白 Z 的第一个表皮生长因子样结构域中发现的二糖和三糖序列及其与丝氨酸的结合物。二糖 α-D-Xylp(1→3)-D-Glcp 由 2,3,4-三-O-苄基-α-D-吡喃木糖基氟和烯丙基 2,4,6-三-O-乙酰基制备-α-D-吡喃葡萄糖苷 (9a) 使用氯化锡 (II) 和高氯酸银作为糖基化试剂。三糖 α-D-Xylp(1→3)-α-D-Xylp(1→3)-D-Glcp 由 O-(2,3,4-tri-O-benzyl-α-D-xylopyranosyl )-(1→3)-2,4-二-O-苄基-α,β-D-吡喃木糖基氟和9a用相同的试剂。它们与丝氨酸、α-D-Xylp(1→3)-β-D-Glcp(1→3)-L-Ser 和 α-D-Xylp(1→3)-α-D-Xylp(1→ 3)-β-D-Glcp(1→3)-L-Ser，通过
• Anomeric alkylations and acylations of unprotected mono- and disaccharides mediated by pyridoneimine in aqueous solutions
  作者：Kalyan Dey、Narayanaswamy Jayaraman

  DOI：10.1039/d1cc07056h

  日期：——

  A site-specific deprotonation followed by alkylations and acylations of sugar hemiacetals to the corresponding alkyl glycosides and acylated sugars in aqueous solutions is disclosed herein. Pyridoneimine as a new base is developed to mediate the deprotonation of readily available sugar hemiacetals and further reactions with alkylation and acylation agents.

  本文公开了在水溶液中进行位点特异性去质子化，随后将糖半缩醛烷基化和酰化为相应的烷基糖苷和酰化糖。吡啶酮亚胺作为一种新的碱被开发用于介导容易获得的糖半缩醛的去质子化以及与烷基化和酰化剂的进一步反应。
• Glycosidase inhibitors and methods of synthesizing same
  申请人：Pinto Mario Brian

  公开号：US20050065139A1

  公开（公告）日：2005-03-24

  A method for synthesizing Salacinol, its stereoisomers, and analogues, homologues and other derivatives thereof potentially useful as glycolsidase inhibitors. The compounds of the invention may have the general formula (I) or (II): The synthetic schemes comprise reacting a cyclic sulfate with a 5-membered ring sugar containing a heteroatom (X). The heteroatom preferably comprises sulfur, selenium, or nitrogen. The cyclic sulfate and ring sugar reagents may be readily prepared from carbohydrate precursors, such as D-glucose, L-glucose, D-xylose and L-xylose. The target compounds are prepared by opening of the cyclic sulfates by nucleophilic attack of the heteroatoms on the 5-membered ring sugars. The resulting heterocyclic compounds have a stable, inner salt structure comprising a heteroatom cation and a sulfate anion. The synthetic schemes yield various stereoisomers of the target compounds in moderate to good yields with limited side-reactions.

  一种合成Salacinol及其立体异构体、类似物、同系物和其他衍生物的方法，可能用作糖苷酶抑制剂。本发明的化合物可能具有一般式(I)或(II)：合成方案包括将环状硫酸酯与含有杂原子(X)的5元环糖反应。杂原子优选包括硫、硒或氮。环状硫酸酯和环糖试剂可以从碳水化合物前体（如D-葡萄糖、L-葡萄糖、D-木糖和L-木糖）中轻松制备。目标化合物是通过杂原子对5元环糖的亲核攻击打开环状硫酸酯来制备的。所得的杂环化合物具有稳定的内盐结构，包括一个杂原子阳离子和一个硫酸酯阴离子。合成方案以中等至良好的产率产生目标化合物的各种立体异构体，副反应有限。
• Green glycosylation promoted by reusable biomass carbonaceous solid acid: an easy access to β-stereoselective terpene galactosides
  作者：Bala Kishan Gorityala、Jimei Ma、Kalyan Kumar Pasunooti、Shuting Cai、Xue-Wei Liu

  DOI：10.1039/c0gc00883d

  日期：——

  An efficient green protocol has been developed for the atom economic glycosylation of unprotected, unactivated glycosyl donors and glycosylation of glycosyl trichloroacetimidates with the aid of reusable eco-friendly biomass carbonaceous solid acid as catalyst.

  开发了一种高效的绿色协议，用于无保护、未活化的糖苷供体的原子经济糖苷化，以及在可重复使用的环保生物质碳酸固体酸催化剂的帮助下对糖苷三氯乙酰亚胺的糖苷化。