methyl 2-deoxy-3-O-benzyl-β-D-erythro-pentofuranoside | 113666-60-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2-deoxy-3-O-benzyl-β-D-erythro-pentofuranoside
• 英文别名: methyl 3-O-benzyl-2-deoxy-β-D-ribofuranoside；Methyl 3-O-benzyl-2-deoxy-β-D-erythro-pentofuranoside；[(2R,3S,5R)-5-methoxy-3-phenylmethoxyoxolan-2-yl]methanol
• CAS: 113666-60-7
• 化学式: C₁₃H₁₈O₄
• 分子量: 238.284
• InChiKey: KSWAOVQCBZRJED-YNEHKIRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-deoxy-3-O-benzyl-β-D-erythro-pentofuranoside 在 吡啶 、 咪唑 、 chromium(VI) oxide 、 盐酸 、 氢氧化钾 、 ammonium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 cerium(III) chloride 、 草酰氯 、 乙酸酐 、 二甲基亚砜 、 三乙胺 、 三苯基膦 、 calcium carbonate 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 二氯甲烷 、 苯 为溶剂， 反应 115.42h， 生成 methyl 2,6-dideoxy-3-C-methyl-α-L-xylo-hexopyranoside
  参考文献：
  名称：

  Stereoselectivity of Addition of Organometallic Reagents to Pentodialdo-1,4-furanoses: Synthesis of L-Axenose and D-Evermicose from a Common Intermediate

  摘要：

  The additions of organometallic reagents to two pentodialdo-1,4-furanosides (methyl 3-O-benzyl-2-deoxy-alpha-D-erythro-pentofuranoside and its beta-anomer) were carried out under a variety of experimental conditions. Methylmagnesium halides, methyllithium, methylcerium and the organotitanium reagent MeTi(OiPr)(3) were reacted with the pentodialdo-1,4-furanosides in an effort to determine if the stereoselectivity of addition to the formyl group is the result of chelation or nonchelation control and to determine the effect of anomeric configuration. The stereochemistry of the products was assigned by NMR methods and correlation with known compounds synthesized previously. The stereoselectivity of addition depends on the configuration at the anomeric center of the dialdose, with the beta-anomer giving mainly the product of a non-chelation-controlled addition and the beta-anomer giving the opposite stereoselectivity. The major product obtained from the beta-anomer was utilized as a key intermediate in the synthesis of two branched-chain carbohydrates, axenose and evermicose, found in antibiotics. Methylcerium additions are the most efficient method for introducing the branching methyl group in a 2-deoxyfuranosid-3-ulose.

  DOI：

  10.1021/jo00106a035
• 作为产物：
  描述：

  (2S,3R)-2-<3,4-O-isopropylidene-2,3,4-trihydroxybut-1-yl>-1,3-dithiane 在 盐酸 、 水 、 sodium hydride 、 calcium carbonate 、 碘甲烷 作用下， 以 乙腈 为溶剂， 反应 29.83h， 生成 methyl 2-deoxy-3-O-benzyl-β-D-erythro-pentofuranoside
  参考文献：
  名称：

  Chemistry of L-ascorbic and D-isoascorbic acids. 4. An efficient synthesis of 2-deoxypentofuranoses

  摘要：

  DOI：

  10.1021/jo00301a035

文献信息

• Zinc-Catalyzed Phosphonylation of Alcohols with Alkyl Phosphites
  作者：Yuki Saito、Soo Min Cho、Luca Alessandro Danieli、Shu̅ Kobayashi

  DOI：10.1021/acs.orglett.0c00932

  日期：2020.4.17

  (Zn(TMHD)2), primary, secondary, and tertiary alcohol substituents on a wide range of substrates, including acyclic and cyclic structures, carbohydrates, steroids, and amino acids, reacted with dimethyl phosphite to afford the corresponding H-phosphonate diesters in high to excellent yields.

  在催化量的Zn（acac）2或双（2,2,6,6-四甲基-3,5-庚二酮基）锌（II）（Zn（TMHD）2），伯，仲和广泛的底物（包括无环和环状结构，碳水化合物，类固醇和氨基酸）上的叔醇取代基与亚磷酸二甲酯反应，以高收率或优异的收率得到相应的H-膦酸酯二酯。
• Cyclic platelet-activating factor analogues derived from 2-deoxy-d-erythro-pentose
  作者：Michael L. Phillips、Rosanne Bonjouklian

  DOI：10.1016/0008-6215(86)85026-1

  日期：1986.1

  A method for the synthesis of chiral cyclic analogues of platelet-activating factor (PAF) is reported. Treatment of suitably substituted derivatives of 2-deoxy-D-erythro-pentose with phosphorus oxychloride, followed by choline p-toluenesulfonate generates cyclic phospholipids in good yield. Further chemical modification produces other compounds including optically active gamma-butyrolactones such as

  报道了一种合成血小板活化因子（PAF）的手性环状类似物的方法。用氯氧化磷处理2-脱氧-D-赤-戊糖的适当取代的衍生物，然后用胆碱对甲苯磺酸盐处理，可以高收率产生环状磷脂。进一步的化学修饰会产生其他化合物，包括旋光性的γ-丁内酯，例如2-脱氧-5-O-十六烷基-3-O-磷胆酰基-D-赤型戊酮-1、4-内酯和2-脱氧-3-O-十六烷基-5-O-磷胆酰基-D-赤-戊基-1，4-内酯。所有磷脂都是PAF诱导的人血小板聚集的弱拮抗剂，而两个类似物是弱激动剂。提出的化学方法对于合成其他构象受限的PAF类似物应该是有用的。
• Sugar-Modified Foldamers as Conformationally Defined and Biologically Distinct Glycopeptide Mimics
  作者：Aloysius Siriwardena、Kiran Kumar Pulukuri、Pancham S. Kandiyal、Saumya Roy、Omprakash Bande、Subhash Ghosh、José Manuel Garcia Fernández、Fernando Ariel Martin、Jean-Marc Ghigo、Christophe Beloin、Keigo Ito、Robert J. Woods、Ravi Sankar Ampapathi、Tushar Kanti Chakraborty

  DOI：10.1002/anie.201304239

  日期：2013.9.23

  To fold or not to fold? It is shown that attached sugars play a defining role in the conformations adopted by a pair of novel SAA‐derived foldamers in water and that these differences are reflected in the contrasting interactions of these glycofoldamers with various biological targets. C green, O red, N blue, H gray; yellow oval=mannose.

  折叠还是不折叠？结果表明，附着的糖在水中一对新型 SAA 衍生折叠体所采用的构象中起着决定性作用，并且这些差异反映在这些糖折叠体与各种生物靶标的对比相互作用中。C绿、O红、N蓝、H灰；黄色椭圆形=甘露糖。
• A highly efficient catalytic method for the synthesis of phosphite diesters
  作者：Yuki Saito、Soo Min Cho、Luca Alessandro Danieli、Akira Matsunaga、Shū Kobayashi

  DOI：10.1039/d4sc01401d

  日期：——

  In contrast to conventional methods that rely on stoichiometric activation of phosphonylating reagents, we have developed a highly efficient catalytic method for the synthesis of phosphite diesters using a readily available phosphonylation reagent and alcohols with environmentally benign Zn(II) catalysts. Two alcohols could be introduced consecutively on the P center with release of trifluoroethanol

  与依赖膦酰化试剂化学计量活化的传统方法相比，我们开发了一种高效的催化方法，使用易于获得的膦酰化试剂和醇以及环境友好的 Zn( II ) 催化剂来合成亚磷酸二酯。在温和条件下，可以在 P 中心连续引入两种醇，并释放三氟乙醇作为唯一的副产物，无需任何添加剂。产物能顺利氧化生成磷酸三酯。一系列醇，包括空间要求高和高度官能化的醇，例如碳水化合物和核苷，都可以应用于该反应。
• Monoglycosyl, diglycosyl, and dinucleoside methylenediphosphonates: direct synthesis and antiviral activity
  作者：Claude Grison、Stéphane Joliez、E. De Clercq、Philippe Coutrot

  DOI：10.1016/j.carres.2006.03.023

  日期：2006.7

  A direct and general access to D-glycosyl 3-, 5-, or 6-methylenediphosphonates, di-D-glycosyl 1,5-, 3,5-, 3,6-, 5,5-, or 6,6-methylenediphosphonates and dithymidine 3',5'-methylenediphosphonate is described. The method involves the one-pot alkylidenediphosphorylation of glycosyl or thymidine derivatives. No antiviral activity was detected against a panel of RNA and DNA viruses. (c) 2006 Elsevier Ltd. All rights reserved.