| 149207-10-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• CAS: 149207-10-3
• 化学式: C₁₆H₂₀O₅
• 分子量: 292.332
• InChiKey: NXGBZPLOQHPAKZ-KBUPBQIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.89
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  在 palladium dihydroxide 吡啶 、 sodium hydroxide 、 氢气 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 100.0h， 生成 Methanesulfonic acid (3aR,6S,6aR)-6-hydroxymethyl-5-methanesulfonyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester
  参考文献：
  名称：

  胸腺嘧啶核苷与3'，4'-四氢呋喃环稠合的合成及生物学评价。

  摘要：

  从1,2; 5,6-di-O-异亚丙基-D-葡萄糖开始，成功合成了与3'，4'-四氢呋喃环稠合的嘧啶核苷，并测定了其对HIV-1，HIV-2， EMCV，考克斯。B3和VSV。胸腺嘧啶类似物（5）及其相应的2'-脱氧类似物（6）表现出高细胞毒性，而不具有抗病毒活性。

  DOI：

  10.1016/s0960-894x(03)00730-3
• 作为产物：
  描述：

  3-deoxy-3-hydroxymethyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose 在 sodium periodate 、 硫酸 、 sodium hydride 作用下， 以 甲醇 为溶剂， 反应 64.17h， 生成
  参考文献：
  名称：

  核苷和核苷酸。147.含有氧杂环丁烷素A和（2 R，3 R）-2 - C-（腺嘌呤-9-基）-1,4-脱水-2,3-二脱氧-3-C-羟甲基-D-的DNA十二聚体的合成阿拉伯糖醇

  摘要：

  羟色胺A（1）和（2 R，3 R）-2 - C-（腺嘌呤-9-基）-1,4-脱水-2,3-二脱氧-3-C-羟基-甲基-D-阿拉伯糖醇（2），扩环的氧杂环丁烷类似物，被掺入DNA十二聚体中，5'-d（CGCG1ATTCGCG）-3'（II），5'-d（CGCGA 1 TTCGCG）-3'（III），5'-d （CGCG 2 ATTCGCG）-3'（IV）和5'-d（CGCGA 2 TTCGCG）-3'（V）。II，III，IV和V与母体十二聚体5'-d（CGCGAATTCGCG）-3'的热诱导跃迁（I在含有0.01 M磷酸钠（pH 7.0），0.02 M NaCl和6μM每个十二聚体的缓冲液中在260 nm处监测）。Tms的顺序为40°C（I）> 37°C（IV）> 36°C（V）> 34°C（II）> 32°C（III）。含有2的寡核苷酸比未经修饰的DNA十二聚体对蛇毒磷酸二酯酶的抵抗力更高（I）。

  DOI：

  10.1016/0040-4020(96)00007-5

文献信息

• SYNTHESIS OF NOVEL 3′-DEOXY-3′-<i>C</i>-HYDROXYMETHYL NUCLEOSIDES WITH CONFORMATIONALLY RIGID SUGAR MOIETY AS POTENTIAL ANTIVIRAL AGENTS
  作者：Moon Woo Chun、Myung Jung Kim、Un Hee Jo、Joong Hyup Kim、Hee-Doo Kim、Lak Shin Jeong

  DOI：10.1081/ncn-100002354

  日期：2001.3.31

  Based on the fact that the ring expanded 3′-C-hydroxymethyl analogue of oxetanocin A exhibited potent antiviral activity, two types of conformationally rigid 3′-C-hydroxymethyl derivatives in which 2′-hydroxyl group is linked to the 4′-position or to the 6′-position were synthesized starting from 1,2;5,6-di-O-isopropylidene-D-glucose, respectively.

  基于氧杂环丁烷素A的扩环3'-C-羟甲基类似物表现出强大的抗病毒活性这一事实，将2'-羟基连接到4'-位置的两种构象刚性3'-C-羟甲基衍生物分别从1,2; 5,6-二-O-异亚丙基-D-葡萄糖开始合成或至6'-位。
• Synthetic Studies of Rifamycins. V. A Chiral Synthesis of an Ansa-chain Compound for the C-17–C-29 Portion of Rifamycin W
  作者：Masaya Nakata、Hiroyuki Enari、Mitsuhiro Kinoshita

  DOI：10.1246/bcsj.55.3283

  日期：1982.10

  The chiral synthesis of methyl 5,7,9-tri-O-acetyl-2-C-(acetoxymethyl)-2,4,6,8,10,11,12-heptadeoxy-4,6,8,10-tetra-C-methyl-aldehydo-l-glycero-l-talo-l-manno-(E)-11-tridecenuronate 1-(dimethyl acetal) (III), a useful synthetic segment for the C-17-C-29 portion of rifamycin W, is described. The key intermediate, 3-O-(t-butyldimethylsilyl)-2,4,7-trideoxy-5,6-O-isopropylidene-2,4-di-C-methyl-aldehydo-d-glycero-d-talo-heptose (28) was synthesized in 30% yield from methyl 4,6-O-benzylidene-3-deoxy-3-C-methyl-α-d-glucopyranoside in 15 steps. The synthesis involves key steps of highly stereoselective Grignard reaction and regiospecific cis-epoxide ring-opening reaction. The condensation of 28 with 3,3-diethoxy-2-lithio-1-propene afforded about 1.6:1 excess of the “Cram” product (30, 56% yield). The desilylation of 30 followed by homogeneous hydrogenation with (Ph3P)3RhCl gave only the erythro product 34. 3,5-Di-O-benzyl-2,4,6-trideoxy-2,4,6-tri-C-methyl-l-glycero-l-manmo-heptodialdose 1-(diethyl acetal) derived from 34, condensed with the lithium reagent prepared (in ether at −95–−90 °C) from butyllithium and 3-C-(benzyloxymethyl)-3,5,6-trideoxy-5-iodo-1,2-O-isopropylidene-α-d-hexenofuranose, derived from 3-deoxy-3-C-hydroxymethyl-1,2 : 5,6-di-O-isopropylidene-α-d-allofuranose, to afford a 4 : 1 mixture of the “Cram” product and its epimer in 80% yield. The homogeneous hydrogenation of the mixture followed by the debenzylation gave the diastereomerically pure major product, which could be transformed into III in 6 steps.

  本文介绍了 5,7,9-三-O-乙酰基-2-C-（乙酰氧甲基）-2,4,6,8,10,11,12-庚二氧基-4,6,8,10-四-C-甲基-aldehydo-l-甘油-l-talo-l-manno-(E)-11-十三烯脲酸甲酯 1-（二甲基乙缩醛）(III)的手性合成，这是利福霉素 W 的 C-17-C-29 部分的有用合成片段。关键中间体 3-O-(叔丁基二甲基硅烷基)-2,4,7-三脱氧-5,6-O-异亚丙基-2,4-二-C-甲基-醛基-d-缩水甘油-d-庚糖 (28) 是由甲基 4,6-O-亚苄基-3-脱氧-3-C-甲基-α-d-吡喃葡萄糖苷经 15 个步骤合成的，收率为 30%。合成的关键步骤包括高度立体选择性的格氏反应和区域特异性的顺式环氧化物开环反应。28 与 3,3-二乙氧基-2-二硫代-1-丙烯缩合后，可得到过量的 "Cram "产物（30，产率 56%），过量率约为 1.6:1。对 30 进行脱硅处理，然后用 (Ph3P)3RhCl 进行均相氢化，只得到赤式产物 34。由 34 生成的 3,5-二-O-苄基-2,4,6-三脱氧-2,4,6-三-C-甲基-l-甘油-l-芒诺-庚二缩醛 1-（二乙基缩醛）、与丁锂和 3-C-(苄氧基甲基)-3,5,6-三脱氧-5-碘-1,2-O-异亚丙基-α-d-己烯呋喃糖制备的锂试剂（在乙醚中，-95-90 °C）缩合，该试剂由 3-deoxy-3-C-hydroxymethyl-1,2 ：5,6-二-O-异亚丙基-α-d-异呋喃糖，得到 4 : 1 的 "Cram "产品及其表聚物混合物，收率为 80%。对混合物进行均相氢化，然后进行去苄基化反应，得到非对映纯的主要产物，该产物可通过 6 个步骤转化为 III。
• Synthesis and Biological Evaluation of Pyrimidine Nucleosides Fused with 3′,4′-Tetrahydrofuran Ring
  作者：Moon Woo Chun、Myong Jung Kim、Hea Ok Kim、Hyung Ryong Moon、Hee-Doo Kim、Joong Hyup Kim、Lak Shin Jeong

  DOI：10.1081/ncn-120022618

  日期：2003.10

  Pyrimidine nucleosides fused with 3,4'-tetrahydrofuran ring were synthesized, starting from 1,2;5,6-di-O-isopropylidene-D-glucose and assayed for antiviral activities. Thymine analogue 1 and its corresponding 2'-deoxy analogue 3 exhibited high cytotoxicity instead of giving antiviral activities.
• Synthesis of 3′-Acetamidoadenosine Derivatives as Potential A₃Adenosine Receptor Agonists
  作者：Moon Woo Chun、Sung Wook Choi、Tae Kyung Kang、Won Jun Choi、Hea Ok Kim、Zhan-Guo Gao、Kenneth A. Jacobson、Lak Shin Jeong

  DOI：10.1080/15257770801944436

  日期：2008.4.4

  On the basis of high binding affinity of 3'-aminoadenosine derivatives 2b at the human A(3) adenosine receptor (AR), 3'-acetamidoadenosine derivatives 3a-e were synthesized from 1,2:5,6-di-O-isopropylidene-D-glucose via stereoselective hydroboration as a key step. Although all synthesized compounds were totally devoid of binding affinity at the human A(3)AR, our results revealed that 3'-position of adenosine can only be tolerated with small size of a hydrogen bonding donor like hydroxyl or amino group in the binding site of human A(3)AR.
• First asymmetric synthesis of (+)- and (−)-Roccellaric acid and dihydroprotolichesterinic acid
  作者：Johann Mulzer、Nabiollah Salimi、Hans Hartl

  DOI：10.1016/s0957-4166(00)86089-9

  日期：1993.3

  Stereocontrolled syntheses of the title compounds from (R)-2,3-isopropylidene glyceraldehyde, (S)-O-THP-lactaldehyde and 1,2:5,6-Di-O-isopropylidene-alpha-D-glucofuranose (''diacetone-D-glucose'') are described.