allyl β-D-xylopyranoside | 73787-48-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl β-D-xylopyranoside
• 英文别名: (2R,3R,4S,5R)-2-prop-2-enoxyoxane-3,4,5-triol
• CAS: 73787-48-1
• 化学式: C₈H₁₄O₅
• 分子量: 190.196
• InChiKey: SQPCRAFFYUVIQE-ULAWRXDQSA-N

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 β-D-xylopyranoside 在 吡啶 、 二正丁基氧化锡 作用下， 生成 Acetic acid (2R,3R,4S,5R)-5-acetoxy-2-allyloxy-3-benzyloxy-tetrahydro-pyran-4-yl ester
  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
• 作为产物：
  描述：

  2,3,4-三-O-乙酰基-α-D-木吡喃糖苷溴 在 sodium methylate 、 氰化汞 作用下， 以 甲醇 为溶剂， 反应 52.0h， 生成 allyl β-D-xylopyranoside
  参考文献：
  名称：

  Regioselective protection strategies for D-xylopyranosides

  摘要：

  The acylation of D-xylopyranosides can be effected at any position by selective hydroxyl activation with dibutyltin oxide in refluxing benzene and proper choice of starting anomer. Methyl 4-O-benzyl-beta-D-xylopyranoside, available from methyl 2,3-O-isopropylidene-beta-D-xylopyranoside, provides the 2- and 3-benzoates, which are easily separable in 85% combined yield. Methyl and allyl beta-D-xylopyranosides, when treated with 1 equiv of dibutyltin and subsequently with benzoyl chloride (1 equiv), yield their corresponding 4-benzoates (80%). The use of 2 equiv of benzoyl chloride provides the 3,4-dibenzoates in excellent yield (90%). The clean conversion to mono- or dibenzoates, depending on the amount of benzoyl chloride added, suggests that the intermediate stannylene acetals provide different activation levels. A pathway involving acylation of an intermediate dibutylchlorostannyl ether is proposed to explain the observed phenomenon. This sequential selective activation is used to afford protection and differentiation of the 3- and 4-positions with a one-pot synthesis of methyl 4-O-benzoyl-3-O-(chloroacetyl)-beta-D-xylopyranoside. Methyl and benzyl alpha-D-xylopyranosides afford the 2,4-dibenzoates in good yield (> 80%) demonstrating 1,3-activation of a triol system. This protection strategy is used to prepare benzyl O-(2,3,5-tri-O-benzoyl-alpha-L-arabinofuranosyl)-(1 --> 3)-2,4-di-O-benzoyl-alpha-D-xylopyranoside from D-xylose and L-arabinose. In the final step, the silver triflate catalyzed glycosylation of benzyl 2,4-di-O-benzoyl-alpha-D-xylopyranoside by 2,3,5-tri-O-benzoyl-alpha-L-arabinofuranosyl chloride is accomplished in 91% yield.

  DOI：

  10.1021/jo00025a013

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。
• β-Selective xylulofuranosylation <i>via</i> a conformationally-restricted glycosyl donor
  作者：Bo-Shun Huang、Todd L. Lowary

  DOI：10.1039/d0ob00260g

  日期：——

  Reported is the first stereoselective method for β-xylulofuranosylation, which employs 3,4-O-xylylene-protected thioglycoside donors.

  报道了第一种β-木糖呋喃糖基选择性方法，该方法使用3,4-O-二甲苯基保护的硫代糖苷供体。
• 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。
• 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。