(2S,3R,4R)-2-(羟甲基)吡咯烷-3,4-二醇盐酸盐 | 114488-33-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: (2S,3R,4R)-2-(羟甲基)吡咯烷-3,4-二醇盐酸盐
• 英文名称: (2S,3R,4R)-2-(hydroxymethyl)pyrrolidine-3,4-diol hydrochloride
• 英文别名: (2S,3R,4R)-2-hydroxymethyl-pyrrolidine-3,4-diol hydrochloride；1,4-Dideoxy-1,4-imino-L-xylitol hydrochloride；(2S,3R,4R)-2-(hydroxymethyl)pyrrolidine-3,4-diol;hydrochloride
• CAS: 114488-33-4
• 化学式: C₅H₁₁NO₃*ClH
• 分子量: 169.608
• InChiKey: PZGVJCJRMKIVLJ-UJPDDDSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.35
• 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：
  77.3
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  methyl-1,3-di-O-isopropylidene-α-D-fructofuranoside 在 咪唑 、 aluminium hydride 、 盐酸 、 palladium 10% on activated carbon 、 氢气 、 碘 、 sodium hydride 、 对甲苯磺酸 、 臭氧 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， -78.0~20.0 ℃ 、405.33 kPa 条件下， 反应 56.58h， 生成 (2S,3R,4R)-2-(羟甲基)吡咯烷-3,4-二醇盐酸盐
  参考文献：
  名称：

  A Versatile Approach to N-Alkylated 1,4-Dideoxy-1,4-imino-d-arabinitols and 1,4-Dideoxy-1,4-imino-l-xylitols

  摘要：

  A versatile and concise synthesis of N-alkylated 1,4-dideoxy-1,4-imino-D-arabinitol and 1,4-dideoxy-1,4-imino-L-xylitol derivatives is described. These were prepared using pseudohemiketal lactams as key intermediates, which in turn were obtained from sucrose. The key intermediates were prepared by a diastereospecific tandem reaction which facilitated the introduction of various substituents on the nitrogen atom of the iminosugars.

  DOI：

  10.1021/jo1020322

文献信息

• Lewis Acid Catalyzed Ring-Opening Reactions of Sugar-Derived Semicyclic N,O-Acetals
  作者：Masaharu Sugiura、Hiroyuki Hagio、Shu Kobayashi

  DOI：10.1002/1522-2675(200211)85:11<3678::aid-hlca3678>3.0.co;2-0

  日期：2002.11

  efficiently synthesized from regular acetyl or methyl glycosides (glucopyranoside, ribofuranoside, arabinofuranoside, and 2-deoxyribofuranoside) and a carbamate by treatment of trimethylsilyl trifluoromethanesulfonate and 4 A molecular sieves. It was found that these N-glycosides underwent Lewis acid catalyzed ring-opening reactions with silylated nucleophiles to give ring-opened amino alcohols with good-to-high

  N-(烷氧基羰基)-N-糖苷(聚氧半环N,O-缩醛) 由常规乙酰基或甲基糖苷(吡喃葡萄糖苷、呋喃核糖苷、阿拉伯呋喃糖苷和2-脱氧呋喃核糖苷) 和氨基甲酸酯通过三甲基甲硅烷基三氟甲磺酸酯和4 A 处理有效合成分子筛。发现这些N-糖苷与硅烷化亲核试剂发生路易斯酸催化的开环反应，得到具有良好至高非对映选择性的开环氨基醇。揭示了反应性顺序，2-脱氧呋喃糖苷 > 阿拉伯呋喃糖苷 > 呋喃糖苷 > 吡喃葡萄糖苷。还用硅烷或氢化二异丁基铝研究了开环还原。发现合适的还原剂取决于所使用的 N-糖苷。糖苷酶抑制剂，（2S，3R，
• [EN] METHODS FOR THE PREPARATION OF ALKENYLAMINES, CYCLIC CARBAMATES OR DITHIOCARBAMATES, AND AMINOALCOHOLS OR AMINOTHIOLS<br/>[FR] PROCÉDÉS POUR LA PRÉPARATION D'ALCÉNYLAMINES, DE CARBAMATES CYCLIQUES OU DE DITHIOCARBAMATES, ET D'AMINOALCOOLS OU D'AMINOTHIOLS
  申请人：VICTORIA LINK LTD

  公开号：WO2010041964A1

  公开（公告）日：2010-04-15

  A method for preparing an alkenylamine, or a salt, solvate or hydrate thereof, is disclosed. The method comprises reacting a alogen-substituted cyclic acetal or a derivative thereof under particular conditions to provide the alkenylamine, which may be optionally converted into a salt, solvate or hydrate thereof. A method for preparing a cyclic carbamate or cyclic dithiocarbamate, or a salt, solvate or hydrate thereof, is also disclosed. The method comprises reacting an alkenylamine under particular conditions to provide the cyclic carbamate or cyclic dithiocarbamate, which may be optionally converted into a salt, solvate or hydrate thereof. A method for preparing a 1,2-aminoalcohol or 1,2-aminothiol, or a salt, solvate or hydrate thereof, is also disclosed. The method comprises forming a cyclic carbamate or cyclic dithiocarbamate from an alkenylamine, and deprotecting the cyclic carbamate or cyclic dithiocarbamate to provide the 1,2-aminoalcohol or 1,2-aminothiol, which may optionally be converted into a salt, solvate or hydrate thereof.

  揭示了一种制备烯基胺或其盐、溶剂合物或水合物的方法。该方法包括在特定条件下反应氯代取代的环缩醛或其衍生物以提供烯基胺，该烯基胺可以选择性地转化为其盐、溶剂合物或水合物。还揭示了一种制备环氨基甲酸酯或环二硫代氨基甲酸酯或其盐、溶剂合物或水合物的方法。该方法包括在特定条件下反应烯基胺以提供环氨基甲酸酯或环二硫代氨基甲酸酯，该化合物可以选择性地转化为其盐、溶剂合物或水合物。还揭示了一种制备1,2-氨基醇或1,2-氨基硫醇或其盐、溶剂合物或水合物的方法。该方法包括从烯基胺中形成环氨基甲酸酯或环二硫代氨基甲酸酯，并去保护环氨基甲酸酯或环二硫代氨基甲酸酯以提供1,2-氨基醇或1,2-氨基硫醇，该化合物可以选择性地转化为其盐、溶剂合物或水合物。
• Facile Synthesis of (2<i>S</i>,3<i>R</i>,4<i>R</i>)-2-Hydroxymethyl-3,4-pyrrolidinediol and 4-Acetamido-1,2,3-tri-<i>O</i>-acetyl-4-deoxy-L-xylopyranose from the Photoproduct of D-Mannose
  作者：Akira Hosaka、Shuji Ichikawa、Hiroko Shindo、Tadashi Sato

  DOI：10.1246/bcsj.62.797

  日期：1989.3

  (Synthesis of 2S,3R,4R)-2-hydroxymethyl-3,4-pyrrolidinediol and 4-acetamido-1,2,3-tri-O-acetyl-4-deoxy-l-xylopyranose were attained in four steps from d-mannose, using iron(III)-catalyzed photoreaction as a key reaction.

  (以铁（III）催化的光反应为关键反应，通过四个步骤从 d-甘露糖合成了 2S,3R,4R）-2-羟甲基-3,4-吡咯烷二醇和 4-乙酰氨基-1,2,3-O-三乙酰基-4-脱氧-l-木吡喃糖。
• A New Synthesis of (2S,3R,4R)-2-(Hydroxymethyl)pyrrolidine-3,4-diol
  作者：Qingchang Meng、Manfred Hesse

  DOI：10.1002/hlca.19910740222

  日期：1991.3.13

  The title compound 6 was synthesized from 2,3,5-tri-O-benzyl-D-arabinofuranose (7) in three steps and 48% overall yield. Moreover, it was shown, in the case of γ-hydroxy amide 9, that the Mitsunobu reaction is not suitable for the preparation of γ-lactams, because O-alkylation is predominant.

  由2,3,5-三-O-苄基-D-阿拉伯呋喃糖（7）分三步合成标题化合物6，总产率为48％。此外，在γ-羟基酰胺9的情况下，由于主要是O-烷基化，因此表明Mitsunobu反应不适合于γ-内酰胺的制备。
• Buchanan, J. Grant; Lumbard, Keith W.; Sturgeon, Robert J., Journal of the Chemical Society. Perkin transactions I, 1990, p. 699 - 706
  作者：Buchanan, J. Grant、Lumbard, Keith W.、Sturgeon, Robert J.、Thompson, Deryk K.

  DOI：——

  日期：——