2,3,5-tri-O-benzyl-1-O-methyl-D-xylofuranoside | 197716-38-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,5-tri-O-benzyl-1-O-methyl-D-xylofuranoside
• 英文别名: methyl 2,3,5-tri-O-benzyl-D-xylo-furanoside；(3R,4S,5R)-2-methoxy-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolane
• CAS: 197716-38-4
• 化学式: C₂₇H₃₀O₅
• 分子量: 434.532
• InChiKey: DJVKHGGGJZLGII-TXVRJSAZSA-N

物化性质

• 沸点：
  552.6±50.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3,5-tri-O-benzyl-1-O-methyl-D-xylofuranoside 在 钯 咪唑 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 四丁基氟化铵 、 silica gel 、 对甲苯磺酸 、 溶剂黄146 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 甲酸 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-hexanoyl-3-[(4R,5R)-5-(methoxymethoxy)-2-phenyl-1,3-dioxan-4-yl]-2H-furan-5-one
  参考文献：
  名称：

  Formal Synthesis of (-)-Syringolide 1 Starting from D-Xylose Based on a Biomimetic Strategy

  摘要：

  An expeditious and practical synthertic process for a nonproteinaceous elicitor, (-)-syringolide 1, has been developed in a short number of steps utilizing the putative biosynthetic pathway by featuring the elaboration of the protected D-xylose as a starting material.

  DOI：

  10.3987/com-97-7926
• 作为产物：
  描述：

  1,2-O-异亚丙基-alpha-D-呋喃木糖 在 盐酸 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 2,3,5-tri-O-benzyl-1-O-methyl-D-xylofuranoside
  参考文献：
  名称：

  Novel Asymmetric Synthesis of an Indolizidine Alkaloid, (+)-Lentiginosine Employing Highly Stereoselective Hydrogenation of α-Hydroxypyrrolidine

  摘要：

  本文介绍了一种高效、新颖的 (1S,2S,8aS)-二羟基吲哚苷生物碱 (+)-lentiginosine 的不对称合成工艺，其中一个关键步骤是对来自 D-木糖的季δ-羟基吡咯烷衍生物进行不对称脱氧。

  DOI：

  10.1055/s-1998-1617

文献信息

• Immunostimulatory and Antitumor Activities of Monoglycosylceramides Having Various Sugar Moieties.
  作者：Kazuhiro MOTOKI、Masahiro MORITA、Eiichi KOBAYASHI、Takeshi UCHIDA、Kohji AKIMOTO、Hideaki FUKUSHIMA、Yasuhiko KOEZUKA

  DOI：10.1248/bpb.18.1487

  日期：——

  Ten kinds of monoglycosylceramides (MonoCers), having the same ceramide portion and different sugar moieties, were synthesized and their immunostimulatory and antitumor activities were examined. The manner of combination between sugar and ceramide has been demonstrated to affect the manifestation of immunostimulatory and resultant antitumor activities of MonoCers, and in the case of D-MonoCers having the D-sugar, α-D-MonoCers (sugar combined to ceramide in an α-configuration) show stronger activities than β-D-MonoCers. Furthermore, the form of sugar, not the furanose-form but the pyranose-form, and the 2''-and 4''-hydroxyl groups of the pyranose-form of sugar, seemed to play an important role in the manifestation of the activities of α-D-MonoCers.

  合成了十种单糖基神经酰胺（MonoCers），它们具有相同的神经酰胺部分和不同的糖基部分，并研究了它们的免疫刺激和抗肿瘤活性。糖与神经酰胺的结合方式已被证明会影响MonoCers的免疫刺激及其相应的抗肿瘤活性的表现。对于含有D-糖的D-MonoCers，α-D-MonoCers（糖以α-构型与神经酰胺结合）显示出比β-D-MonoCers更强的活性。此外，糖的形式，不是呋喃糖形式而是吡喃糖形式，以及吡喃糖形式的糖的2''和4''-羟基，似乎在α-D-MonoCers的活性表现中起着重要作用。
• Iodine Monochloride (ICl) as a Highly Efficient, Green Oxidant for the Oxidation of Alcohols to Corresponding Carbonyl Compounds
  作者：Peng Wei、Datong Zhang、Zhigang Gao、Wenqing Cai、Weiren Xu、Lida Tang、Guilong Zhao

  DOI：10.1080/00397911.2015.1005630

  日期：2015.6.18

  ABSTRACT Iodine monochloride (ICl) was discovered to be a highly efficient, green oxidant, which can oxidize aldose hemiacetals, diarylmethanols, arylalkylmethanols, anddialkylmethanols to the corresponding aldose lactones, diarylmethanones, arylalkylmethanones, and dialkylmethanones, respectively, in high yields. ICl as a green, metal-free oxidant is characterized by mild reaction condition, short reaction

  摘要 一氯化碘 (ICl) 被发现是一种高效的绿色氧化剂，可以将醛糖半缩醛、二芳基甲醇、芳烷基甲醇和二烷基甲醇分别以高产率氧化成相应的醛糖内酯、二芳基甲酮、芳基烷基甲酮和二烷基甲酮。ICl作为一种绿色无金属氧化剂，具有反应条件温和、反应时间短、收率好、适用范围广等特点。图形概要
• The Development of an Aza-C-Glycoside Library Based on a Tandem Staudinger/Aza-Wittig/Ugi Three-Component Reaction
  作者：Tom Wennekes、Kimberly M. Bonger、Katrin Vogel、Richard J. B. H. N. van den Berg、Anneke Strijland、Wilma E. Donker-Koopman、Johannes M. F. G. Aerts、Gijsbert A. van der Marel、Herman S. Overkleeft

  DOI：10.1002/ejoc.201200923

  日期：2012.11

  We report the tandem Staudinger/aza-Wittig/Ugi three-component reaction mediated synthesis of a 64-member compound library of aza-C-glycosides. The library is composed of four pyrrolidine and three piperidine scaffolds, onto which a number of functional groups is grafted to form seven sublibraries. Variation in the library is achieved by transformation of two pentoses and a hexose into the corresponding

  我们报告串联 Staudinger/aza-Wittig/Ugi 三组分反应介导的 aza-C-糖苷 64 成员化合物库的合成。该文库由四个吡咯烷和三个哌啶支架组成，在其上接枝了许多官能团以形成七个子文库。通过将两种戊糖和一种己糖转化为相应的 4-叠氮戊醛和 5-叠氮己醛衍生物作为 Staudinger/aza-Wittig 过程的前体，可以实现文库的变化。通过在完全保护的 Ugi-3CR 中间体上使用不同的异氰化物以及保护和官能团操作，可以实现进一步的变化。化合物库的初步生物学评估揭示了几种低微摩尔人酸性葡糖神经酰胺酶抑制剂
• Synthesis of C-5-thioglycopyranosides and their sulfonium derivatives from 1-C-(2′-oxoalkyl)-5-S-acetylglycofuranosides
  作者：Tian Yi、Shih-Hsiung Wu、Wei Zou

  DOI：10.1016/j.carres.2004.11.014

  日期：2005.2

  D-xylose were converted to 1-C-(2'-oxoalkyl)-5-thioglycopyranosides by base treatment. The transformation was achieved through beta-elimination to an acyclic alpha,beta-conjugated aldehyde (ketone or ester), followed by an intramolecular hetero-Michael addition by the 5-thiol group. The cycloaddition was highly stereoselective in favor of an equatorial 1-C-substitution. The resultant C-5-thioglycopyranosides

  通过碱处理将L-阿拉伯糖，D-核糖和D-木糖的1-C-（2'-氧代烷基）-5-S-乙酰基呋喃糖苷转化为1-C-（2'-氧代烷基）-5-硫代吡喃果糖苷。通过β-消除成无环α，β-共轭醛（酮或酯），然后通过5-硫醇基团进行分子内杂-迈克尔加成，实现了转化。环加成是高度立体选择性的，有利于赤道1-C取代。通过用环状硫酸盐和甲基碘处理，将所得的C-5-硫代糖吡喃果糖苷进一步转化为the盐。由于存在S-轴和S-赤道取代基，获得了两种sulf异构体。
• Functionalized d- and l-Arabino-Pyrrolidines as Potent and Selective Glycosidase Inhibitors
  作者：Emil Lindbäck、Magne O. Sydnes、Marianne B. Haarr、Óscar Lopéz、Jóse G. Fernández-Bolaños

  DOI：10.1055/a-1764-8950

  日期：2022.6

  4-dideoxy-1,4-imino-d-arabinitol (DAB) and 1,4-dideoxy-1,4-imino-l-arabinitol (LAB) analogues with an amidine, hydrazide, hydrazide imide, or amide oxime moiety is described. The preparation of DAB and LAB analogues commenced from l-xylose and d-xylose, respectively. The obtained iminosugars are tested against a panel of glycosidases with pharmaceutical relevance, revealing enhanced activity for the DAB analogues

  摘要用脒高效合成亚氨基糖对映异构体对，包括 1,4-二脱氧-1,4-亚氨基-d-阿拉伯糖醇 (DAB) 和 1,4-二脱氧-1,4-亚氨基-l-阿拉伯糖醇 (LAB) 类似物描述了酰肼、酰肼酰亚胺或酰胺肟部分。DAB 和 LAB 类似物的制备分别从 l-木糖和 d-木糖开始。所获得的亚氨基糖针对一组具有药物相关性的糖苷酶进行了测试，显示与 LAB 类似物相比，DAB 类似物的活性增强。特别是，d-阿拉伯构型的脒表现出强效（亚微摩尔范围）和选择性的α-甘露糖苷酶抑制剂。