methyl 2-deoxy-α-D-erythro-pentopyranoside | 6160-56-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-deoxy-α-D-erythro-pentopyranoside
• 英文别名: methyl 2-deoxy-α-D-arabinopyranoside；methyl 2-deoxy-α-D-ribopyranoside；Me-α-D-ery-dPenp；Methyl 2-deoxy-alpha-D-erythro-pentopyranoside；(3R,4S,6S)-6-methoxyoxane-3,4-diol
• CAS: 6160-56-1
• 化学式: C₆H₁₂O₄
• 分子量: 148.159
• InChiKey: CYLGOSOYSUHPCY-JKUQZMGJSA-N

物化性质

• 沸点：
  271.4±40.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-deoxy-α-D-erythro-pentopyranoside 在 ruthenium trichloride 、 sodium periodate 、 lithium aluminium tetrahydride 、 磺酰氯 、 叠氮化锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 三乙胺 、 乙腈 为溶剂， 反应 25.0h， 生成 1-[(1R,4S,6R)-4-甲氧基-3-氧杂-7-氮杂双环[4.1.0]庚-7-基]乙酮
  参考文献：
  名称：

  的改进的立体选择性合成都是甲基α-和对应于E环的氨基糖成分β糖苷的加利车霉素γ 1我和埃斯波霉素阿1

  摘要：

  的E环的单糖组分（α和β端基异构体）刺孢霉素γ 1我和埃斯波霉素阿1已经通过从甲基2-脱氧- α-和β-d-ribopyranoside开始的有效和改进的立体选择性方法合成。在每种情况下，合成方法都使用环状硫酸盐和中间体活化的氮丙啶的区域选择性开环。

  DOI：

  10.1016/s0040-4020(97)00921-6
• 作为产物：
  描述：

  甲醇 、 2-deoxy-D-ribose 在 盐酸 作用下， 以0.82 g的产率得到methyl 2-deoxy-α-D-erythro-pentopyranoside
  参考文献：
  名称：

  加利车霉素的氨基糖成分（E环）的一个有效的立体选择性合成γ 1我

  摘要：

  一种简单，高效，立体选择性的甲基2,4-二脱氧-4-（乙基氨基）-3 - O-甲基-β-L-苏-戊吡喃糖苷2的合成，对应于E的单糖单元（E环）描述了加利车霉素1。合成程序利用甲基2-脱氧-β-D-核糖吡喃糖苷3作为对映体纯原料，并通过中间体活化的氮丙啶12的酸甲醇分解，分6步得到所需的氨基糖2，令人满意的高总收率（60％ ）。在合成过程的任何时候都不需要分离阶段。

  DOI：

  10.1016/0957-4166(96)00074-2

文献信息

• [EN] PROCESS FOR THE PREPARATION OF (2R.3S)-2-(HYDROXYMETHYL) -5-METHOXYTETRAHYDROFURAN-3-OL AND ACETYLATED DERIVATIVES THEREOF, FREE OF PYRANOSE COMPOUNDS<br/>[FR] PROCÉDÉ POUR LA PRÉPARATION DU (2R,3S)-2-(HYDROXYMÉTHYL)-5-MÉTHOXYTÉTRAHYDROFURAN-3-OL ET DE DÉRIVÉS ACÉTYLÉS DE CELUI-CI, EXEMPTS DE COMPOSÉS DE PYRANOSE
  申请人：JOHNSON MATTHEW PLC

  公开号：WO2012071508A1

  公开（公告）日：2012-05-31

  A method of preparing a ribofuranose derivative essentially free of pyranose compounds includes a step of contacting a solution of MDR containing MDRP as an impurity in a solvent including methanol and/or tetrahydrofuran with at least one alkali metal periodate under conditions sufficient to oxidize at least a portion of the MDRP. MDR containing at most 5 wt% of MDRP based on the total weight of MDR and MDRP may be produced.

  一种制备基本无吡喃糖衍生物的核糖醇衍生物的方法，包括以下步骤：将包含MDRP杂质的MDR溶液在包括甲醇和/或四氢呋喃的溶剂中与至少一种碱金属过碘酸盐接触，以使至少部分MDRP被氧化。可以制备含有MDRP最多占MDR和MDRP总重量的5wt％的MDR。
• 4'-Thio-Nucleosides via in Situ Pyranose-Furanose Rearrangements: A Short Synthesis of the Antiherpes Agent 2'-Deoxy-5-ethyl-4'-thiouridine via Direct Coupling of a Silylated Pyrimidine Base with a 4-Thiopyranose Sugar
  作者：Karamjit Singh Jandu、David L. Selwood

  DOI：10.1021/jo00121a039

  日期：1995.8

  Methyl 2-deoxy-3,4-0-thiocarbonyl-beta-D-ribopyranoside was converted into the thione carbonate by reaction with thiophosgene. Bromide ion-catalyzed 0-S rearrangement produced methyl 2-deoxy-3-0,4-S-carbonyl-4-thio-beta-D-ribopyranoside (3a) and the 3-0,4-S isomer 3b. The carbonates were cleaved with ammonia and the 3-0,4-S pyranoside sugar coupled with bis(trimethylsilyl)-5-ethyluracil using trimethylsilyl triflate to provide the antiherpes agent 2'-deoxy-5-ethyl-4'-thiouridine 9. The reaction proceeded via in, situ pyranoside rearrangement-of the sugar and subsequent coupling. The pyranoside sugar could also be converted to the furanoside form with Dowex H+ acid resin and coupled in conventional fashion to give the nucleoside. Coupling of methyl 4-0-carbamoyl-2-deoxy-3-thio-beta-D-ribopyranoside (4b) with the bis(trimethylsilyl)-5-ethyluracil gave 1-[2-[2-(hydroxymethyl)thiiran-1-yl]-1-methoxyethyl]-5-ethyluracil.
• Phenylboronic acid esters of the common 2-deoxy-aldoses
  作者：David Heß、Peter Klüfers

  DOI：10.1016/j.carres.2011.05.031

  日期：2011.9

  Phenylboronic acid esters are formed by the three common 2-deoxy aldoses: 2-deoxy-D-erythro-pentose ('2-deoxy-D-ribose'), 2-deoxy-D-lyxo-hexose ('2-deoxy-D-galactose'), and 2-deoxy-D-arabino-hexose ('2deoxy-D-glucose'). The major species that was formed from equimolar quantities of boronic acid and the aldose, was the 3,4-monoester of the pentopyranose in a skew-boat conformation, and the 4,6-monoester in the case of the two hexopyranoses. A double molar quantity of boronic acid led, for both 2-deoxyhexoses, to the diester of the open-chain aldehydo isomer as the major product: the 3,5: 4,6-diester for the lyxo-configured deoxy-hexose, and the 3,4:5,6-diester of the arabino-configured isomer. Minor products of all reactions were identified by a combined NMR/DFT methodology. (C) 2011 Elsevier Ltd. All rights reserved.
• EP0195805A4
  申请人：——

  公开号：EP0195805A4

  公开（公告）日：1987-07-09
• PROCESS FOR MAKING A 2-DEOXYURIDINE
  申请人：SCM CORPORATION

  公开号：EP0195805A1

  公开（公告）日：1986-10-01