5-O-benzyl-2,3-O-isopropylidene-D-ribofuranose | 198969-39-0

• 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: 5-O-benzyl-2,3-O-isopropylidene-D-ribofuranose
• 英文别名: (3aR,6R,6aR)-2,2-dimethyl-6-(phenylmethoxymethyl)-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-ol
• CAS: 198969-39-0
• 化学式: C₁₅H₂₀O₅
• 分子量: 280.321
• InChiKey: YPAOSXPSJGYURT-ZHZAVPAVSA-N

物化性质

• 沸点：
  418.9±45.0 °C(Predicted)
• 密度：
  1.187±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  5-O-benzyl-2,3-O-isopropylidene-D-ribofuranose 在 咪唑 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 1-O-tert-butyldiphenylsilyl-5-O-benzyl-2,3-O-isopropylidene-D-ribitol
  参考文献：
  名称：

  Synthetic studies toward the preparation of (4R,5R)-(−)-3-[(benzyloxy)methyl]-4,5-O-isopropylidene-cyclopenten-2-one: an important synthetic intermediate for carbanucleosides

  摘要：

  The carbocyclic compound (4R,5R)-(-)-3-[(benzyloxy)methyl]-4,5-O-isopropylidene-2-cyclopentenone 1 is an important synthetic intermediate to access a variety of carbanucleosides. Herein, synthetic studies that lead to this valuable compound employing inexpensive D-ribose as the chiral source are presented. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.069
• 作为产物：
  描述：

  allyl 2,3-O-isopropylidene-β-D-ribofuranoside 在 甲醇 、 potassium tert-butylate 、 sodium hydride 、 臭氧 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 35.0h， 生成 5-O-benzyl-2,3-O-isopropylidene-D-ribofuranose
  参考文献：
  名称：

  Synthetic studies toward the preparation of (4R,5R)-(−)-3-[(benzyloxy)methyl]-4,5-O-isopropylidene-cyclopenten-2-one: an important synthetic intermediate for carbanucleosides

  摘要：

  The carbocyclic compound (4R,5R)-(-)-3-[(benzyloxy)methyl]-4,5-O-isopropylidene-2-cyclopentenone 1 is an important synthetic intermediate to access a variety of carbanucleosides. Herein, synthetic studies that lead to this valuable compound employing inexpensive D-ribose as the chiral source are presented. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.069

文献信息

• [EN] NUCLEOTIDE AND NUCLEOSIDE THERAPEUTIC COMPOSITIONS AND USES RELATED THERETO<br/>[FR] COMPOSITIONS THÉRAPEUTIQUES À BASE DE NUCLÉOTIDES ET NUCLÉOSIDES ET UTILISATIONS ASSOCIÉES
  申请人：UNIV EMORY

  公开号：WO2017155923A1

  公开（公告）日：2017-09-14

  This disclosure relates to nucleotide and nucleoside therapeutic compositions and uses in treating infectious diseases, viral infections, and cancer, where the base of the nucleotide or nucleoside contains at least one thiol, thione or thioether.

  这份披露涉及到核苷酸和核苷类治疗组合物，用于治疗传染病、病毒感染和癌症，在这些组合物中，核苷酸或核苷的碱基至少含有一个硫醇、硫酮或硫醚。
• Highly regioselective and stereoselective synthesis of C-Aryl glycosides <i>via</i> nickel-catalyzed <i>ortho</i>-C–H glycosylation of 8-aminoquinoline benzamides
  作者：Wei-Yu Shi、Ya-Nan Ding、Nian Zheng、Xue-Ya Gou、Zhe Zhang、Xi Chen、Yu-Yong Luan、Zhi-Jie Niu、Yong-Min Liang

  DOI：10.1039/d1cc03589d

  日期：——

  C-Aryl glycosides are of high value as drug candidates. Here a novel and cost-effective nickel catalyzed ortho-CAr–H glycosylation reaction with high regioselectivity and excellent α-selectivity is described. This method shows great functional group compatibility with various glycosides, showing its synthetic potential. Mechanistic studies indicate that C–H activation could be the rate-determining

  C-芳基糖苷作为候选药物具有很高的价值。本文描述了一种新颖且经济高效的镍催化邻-C Ar -H 糖基化反应，具有高区域选择性和优异的 α-选择性。该方法与各种糖苷表现出良好的官能团相容性，显示出其合成潜力。机理研究表明 C-H 激活可能是速率决定步骤。
• Titanocene-Catalyzed Reduction of Lactones to Lactols
  作者：Xavier Verdaguer、Marcus C. Hansen、Scott C. Berk、Stephen L. Buchwald

  DOI：10.1021/jo971560s

  日期：1997.11.1

  A convenient method for the conversion of lactones to lactols is described. The hydrosilylation to lactols is carried out via air-stable titanocene difluoride or a titanocene diphenoxide precatalyst using inexpensive polymethylhydrosiloxane (PMHS) as the stoichiometric reductant. These procedures have been demonstrated with a variety of substrates and proceed in good to excellent yield.

  描述了一种方便的将内酯转化为内酯的方法。使用便宜的聚甲基氢硅氧烷（PMHS）作为化学计量的还原剂，通过空气稳定的二茂钛二氟化物或二茂钛二苯醚预催化剂进行氢化硅烷化为乳糖醇。这些步骤已在多种底物上得到证明，并且以良好至极好的收率进行。
• Nickel-catalyzed generation of 2-methylhex-5-enyl ethers from allyl ethers with trimethylaluminium
  作者：Takahiko Taniguchi、Kunio Ogasawara

  DOI：10.1039/a802430h

  日期：——

  Allyl ethers have been converted into the corresponding 2-methylhex-5-enyl ethers in one step on treatment with trimethylaluminium in the presence of a catalytic amount of (dppp)NiCl2.

  丙烯醚在催化量的(dppp)NiCl2存在下，与三甲基铝处理后，已一步转化为相应的2-甲基己-5-烯基醚。
• Synthesis of methyl 2-O-allyl-(and 3-O-allyl-) 5-O-benzyl-β-d-ribofuranoside
  作者：Trupti Desai、Jill Gigg、Roy Gigg

  DOI：10.1016/0008-6215(95)00308-8

  日期：1996.1

  D-Ribose was converted into methyl 5-O-benzyl-beta-D-ribofuranoside and this, on tin-mediated allylation, gave a mixture of the 2-O-allyl and 3-O-allyl derivatives which were separated by chromatography. The more polar isomer was characterised as the 3-O-allyl derivative after conversion via 3-O-allyl-5-O-benzyl-1,2-O-isopropylidene-alpha-D-ribofuranose (which was also synthesised from 3-O-allyl-1

  将D-核糖转化为甲基5-O-苄基-β-D-呋喃呋喃糖苷，并且在锡介导的烯丙基化中，得到2-O-烯丙基和3-O-烯丙基衍生物的混合物，将其通过色谱法分离。通过3-O-烯丙基-5-O-苄基-1,2-O-异亚丙基-α-D-呋喃核糖转化后，更具极性的异构体被表征为3-O-烯丙基衍生物（也由3- O-烯丙基-1，2-：5，6-二-O-异亚丙基-α-D-呋喃糖）成已知的5-O-苄基-1,2-O-异亚丙基-α-D-呋喃核糖。通过甲基2-O-烯丙基-5-O将3-O-烯丙基-5-O-苄基-β-D-呋喃呋喃糖苷转化为甲基2-O-烯丙基-5-O-苄基-β-D-核呋喃糖苷-苄基-3-O-（丙-1-烯）-β-D-呋喃呋喃糖苷。