allyl 2,4-di-O-benzyl-α-D-xylopyranoside | 140420-56-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2,4-di-O-benzyl-α-D-xylopyranoside
• 英文别名: (2S,3R,4S,5R)-3,5-bis(phenylmethoxy)-2-prop-2-enoxyoxan-4-ol
• CAS: 140420-56-0
• 化学式: C₂₂H₂₆O₅
• 分子量: 370.445
• InChiKey: JJGJMCAMYBBWBC-MBDNFAEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  allyl 2,4-di-O-benzyl-α-D-xylopyranoside 在 (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate sodium hydride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成
  参考文献：
  名称：

  Simple Glycosylation Reaction of Allyl Glycosides

  摘要：

  A simple glycosylation strategy employing only allyl glycosides is described. In a one-pot fashion, an allyl glycoside is first isomerized to the reactive 1-prop-en-yl glycoside intermediate, which subsequently undergoes glycosylation with a glycosyl acceptor, promoted by NIS at room temperature.

  DOI：

  10.1021/jo070512x
• 作为产物：
  描述：

  溴甲苯 、 allyl α-D-xylopyranoside 在 sodium hydride 、 oil 作用下， 生成 allyl 2,4-di-O-benzyl-α-D-xylopyranoside
  参考文献：
  名称：

  凝血因子Ⅶ和Ⅸ和蛋白Z中新型丝氨酸连接寡糖的合成.O-α-D-吡喃木糖基-(1→3)-D-吡喃葡萄糖、O-α-D-吡喃木糖基-(1→ 3)-O-α-D-吡喃木糖基-(1→3)-D-吡喃葡萄糖及其与丝氨酸的结合物

  摘要：

  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

  DOI：

  10.1246/bcsj.65.436

文献信息

• 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
• Facile glycosylation strategy with two-stage activation of allyl glycosyl donors. Application to concise synthesis of Shigella flexneri serotype Y O-antigen
  作者：Yun Wang、Xin Zhang、Pengfei Wang

  DOI：10.1039/c002865g

  日期：——

  NIS/TfOH achieves high yields in glycosidic bond construction at room temperature. The efficacy and efficiency of this approach in carbohydrate synthesis is demonstrated in the concise synthesis of the fully protected Shigella flexneri serotype Y O-antigen.

  已经开发出仅使用烯丙基糖苷结构单元的实用的，有用的糖基化方法。供体的糖基化反应性是通过将其异头烯丙基保护基异构化为相应的丙-1-烯基来实现的。随后使用NIS /进行化学选择性激活三氟乙酸在室温下可在糖苷键结构中获得高产量。这种方法在碳水化合物合成中的功效和效率在完全保护的弗氏志贺氏菌血清型的简明合成中得到了证明。ÿ O-抗原。
• Stereoselective α-Glycosylation with 3-O-Acetylated <scp>d</scp>-<i>Gluco</i> Donors
  作者：Nikolay Nifantiev、Nadezhda Ustyuzhanina、Bozhena Komarova、Natalya Zlotina、Vadim Krylov、Alexey Gerbst、Yury Tsvetkov

  DOI：10.1055/s-2006-939037

  日期：——

  The effect of a 3-O-acetyl group on the stereoselectivity of α-glycosylation with 2-O-benzylated D-gluco glycosyl donors was studied. It was shown that 3-O-acetylated donors gave α-anomers predominantly or exclusively, whereas glycosylation with the corresponding per-O-benzylated donors afforded mixtures of comparable amounts of α- and β-anomers. The higher α-stereoselectivity in the first case was

  研究了 3-O-乙酰基对 2-O-苄基化 D-葡萄糖供体的 α-糖基化立体选择性的影响。结果表明，3-O-乙酰化供体主要或仅产生α-端基异构体，而与相应的全-O-苄基化供体的糖基化提供了相当数量的α-和β-端基异构体的混合物。在第一种情况下较高的 α-立体选择性是由 3-O-乙酰基的远程非嵌合辅助解释的，这通过理论计算得到证实。
• Structurally Simple Benzyl-Type Photolabile Protecting Groups for Direct Release of Alcohols and Carboxylic Acids
  作者：Pengfei Wang、Wenya Lu、Dattatray A. Devalankar、Zhenying Ding

  DOI：10.1021/acs.orglett.5b00699

  日期：2015.5.1

  Structurally simple benzyl-type photolabile protecting groups (PPGs) have been developed to release alcohols and carboxylic acids. Release of two substrates from one PPG chromophore has also been accomplished.
• Stereoselective Synthesis of the 3-Aminopropyl Glycosides of α-<scp>d</scp>-Xyl-(1→3)-β-<scp>d</scp>-Glc and α-<scp>d</scp>-Xyl-(1→3)-α-<scp>d</scp>-Xyl-(1→3)-β-<scp>d</scp>-Glc and of Their Corresponding <i>N</i>-Octanoyl Derivatives
  作者：Nikolay Nifantiev、Vadim Krylov、Nadezhda Ustyuzhanina、Alexey Grachev、Hans Bakker

  DOI：10.1055/s-2007-990784

  日期：2007.10

  The stereoselective synthesis of the spacer-armed disaccharide α- D-Xyl-(1→3)-β- D-Glc- O-(CH 2 ) 3 NH 2 and trisaccharide α- D-Xyl-(1→3)-α- D-Xyl-(1→3)-β- D-Glc- O-(CH 2 ) 3 NH 2 , as well as of their N-octanoyl derivatives, was performed for their subsequent use as acceptors and reference samples in xylosyltransferase assays. These structures are found as O-linked glycans on epidermal growth factor

  间隔臂二糖α-D-Xyl-(1→3)-β-D-Glc-O-(CH 2 ) 3 NH 2 和三糖α-D-Xyl-(1→3)-的立体选择性合成α-D-Xyl-(1→3)-β-D-Glc-O-(CH 2 ) 3 NH 2 以及它们的 N-辛酰基衍生物，用于它们随后用作受体和参考样品木糖基转移酶测定。这些结构被发现为几种凝血因子和 Notch 的表皮生长因子 (EGF) 结构域上的 O 连接聚糖。目标产物是通过用 3-O-乙酰化木糖基供体进行糖基化制备的，该供体以前被发现是一种有效的 α-木糖基化剂。然而，在本文中，我们表明糖基受体的结构会影响糖基化的立体化学结果，甚至在一种受体的情况下会导致立体选择性逆转。