(2S,3S,4R,1'S)-3,4-dihydroxy-2-1',2'-dihydroxyethylpyrrolidine | 115509-95-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (2S,3S,4R,1'S)-3,4-dihydroxy-2-1',2'-dihydroxyethylpyrrolidine
• 英文别名: (2S,3S,4R)-2-[(S)-1,2-dihydroxyethyl]pyrrolidine-3,4-diol；1,4-Dideoxy-1,4-imino-D-talitol；1,4-Dideoxy-1,4-imino-D-tallitol；(2S,3S,4R)-2-[(1S)-1,2-dihydroxyethyl]pyrrolidine-3,4-diol
• CAS: 115509-95-0
• 化学式: C₆H₁₃NO₄
• 分子量: 163.174
• InChiKey: RVNSAAIWCWTCTJ-ARQDHWQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  93
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R,1'S)-3,4-dihydroxy-2-1',2'-dihydroxyethylpyrrolidine 在 sodium periodate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.5h， 以2.26 g的产率得到(3aS,4R,6aR)-4-Formyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid benzyl ester
  参考文献：
  名称：

  一些多羟基吡咯烷衍生物的合成。

  摘要：

  聚羟基吡咯烷衍生物7、11、15和18由4合成，4是我们全合成斯温森碱（1）的关键中间体。这些新衍生物的免疫刺激活性适中，低于斯温森碱。

  DOI：

  10.1248/cpb.35.3995
• 作为产物：
  描述：

  2,3,5,6-di-isopropyIidene-1,4-dihydroxy-D-mannitol 在 4-二甲氨基吡啶 、 palladium on activated charcoal 氢气 、 三氟乙酸 作用下， 以 吡啶 、 乙醇 为溶剂， 反应 79.0h， 生成 (2S,3S,4R,1'S)-3,4-dihydroxy-2-1',2'-dihydroxyethylpyrrolidine
  参考文献：
  名称：

  Synthesis from d-mannose of 1,4-dideoxy-1,4-imino-l-ribitol and of the α-mannosidase inhibitor 1,4-dideoxy-1,4-imino-d-talitol

  摘要：

  DOI：

  10.1016/s0040-4020(01)81717-8

文献信息

• Asymmetric Synthesis of d-Proline, d-Pipecolic Acid, (2R,3S,4R)-3,4-Dihydroxyproline, and 1,4-Dideoxy-1,4-imino-d-talitol from a Common Precursor
  作者：Shital Chattopadhyay、Jyoti Mukherjee

  DOI：10.1055/s-0034-1378452

  日期：——

  (2R)-proline, (2R,3S,4R)-3,4-dihydroxyproline, and the known glycosidase inhibiting azasugar 1,4-dideoxy-1,4-imino-d-talitol from a common starting material namely (R)-cyclohexylideneglyceraldehyde in good overall yields. Methodology involving stereoselective aza-Michael addition and ring-closing metathesis as key steps has been developed for the preparation of (2R)-pipecolic acid, (2R)-proline, (2R,3S,4R)-3,4-dihydroxyproline

  摘要 已经开发出以立体选择性aza-Michael加成法和闭环复分解为关键步骤的方法，用于制备（2 R）-哌酸，（2 R）-脯氨酸，（2 R，3 S，4 R）-3， 4- dihydroxyproline，和已知的糖苷酶抑制azasugar 1,4-二脱氧-1,4-亚氨基- d -talitol从一个共同的起始原料即（[R在良好的总收率）-cyclohexylideneglyceraldehyde。 已经开发出以立体选择性aza-Michael加成法和闭环复分解为关键步骤的方法，用于制备（2 R）-哌酸，（2 R）-脯氨酸，（2 R，3 S，4 R）-3， 4- dihydroxyproline，和已知的糖苷酶抑制azasugar 1,4-二脱氧-1,4-亚氨基- d -talitol从一个共同的起始原料即（[R在良好的总收率）-cyclohexylideneglyceraldehyde。
• Synthesis of 1,4-dideoxy-1,4-imino-derivatives of d-allitol, l-allitol and d-talitol: a stereo selective approach for azasugars
  作者：B. Chandrasekhar、A. Madhan、B. Venkateswara Rao

  DOI：10.1016/j.tet.2007.06.044

  日期：2007.9

  approach for the azasugars 1,4-dideoxy-1,4-imino-d-allitol, l-allitol, and 1,4-dideoxy-1,4-imino-d-talitol is described for different olefin compounds I derived from (R)-2,3-O-isopropylidine glyceraldehyde, l-ascorbic acid, and d-isoascorbic acid by using vinyl Grignard addition, allylation, RCM, and dihydroxylation as the key steps.

  对于不同的烯烃化合物I，描述了对氮杂糖1，4-二脱氧-1，4-亚氨基-d-烯丙糖醇，1-烯丙醇和1，4-二脱氧-1，4-亚氨基-d-塔罗糖醇的立体选择性方法。通过将乙烯基格氏试剂加成，烯丙基化，RCM和二羟基化作为关键步骤，衍生自（R）-2,3- O-异丙基甘油醛，1-抗坏血酸和d-异抗坏血酸。
• Epimerization of C5 of an N-hydroxypyrrolidine in the synthesis of swainsonine related iminosugars
  作者：Bao-Chen Qian、Akiko Kamori、Kyoko Kinami、Atsushi Kato、Yi-Xian Li、George W. J. Fleet、Chu-Yi Yu

  DOI：10.1039/c6ob00531d

  日期：——

  Epimerization of C5 of an N-hydroxypyrrolidine ring by regioselective oxidation to a nitrone followed by diastereoselective reduction provides a new approach to the synthesis of swainsonine and related compounds. The only protection in the synthesis of the potent mannosidase inhibitor DIM (1,4-dideoxy-1,4-imino-D-mannitol) was the acetonation of D-mannose.

  N-羟基吡咯烷环的C5通过区域选择性氧化成硝酮然后进行非对映选择性还原的差向异构化提供了一种合成swainsonine和相关化合物的新方法。在有效的甘露糖苷酶抑制剂DIM（1,4- dideoxy -1,4- imino - D-甘露醇）的合成中唯一的保护是D-甘露糖的乙酰化。
• [EN] STABILE CONJUGATE<br/>[FR] CONJUGUÉ STABLE
  申请人：GLYKOS BIOMEDICAL OY

  公开号：WO2021123506A1

  公开（公告）日：2021-06-24

  A conjugate is disclosed. The conjugate may be represented by Formula I: [D-O-L]n-T Formula I wherein D is a payload molecule; O is an oxygen atom of said payload molecule; T is a targeting unit capable of binding a target molecule, cell and/or tissue; and n is at least 1.

  本发明揭示了一种共轭物。该共轭物可以用公式I表示：[D-O-L]n-T 公式I，其中D是荷载分子；O是所述荷载分子的氧原子；T是能够结合目标分子、细胞和/或组织的靶向单元；n至少为1。
• The First Asymmetric Synthesis of 1,4-Dideoxy-1,4-imino-<scp>d</scp>-talitol
  作者：María D. Díaz-de-Villegas、José A. Gálvez、Ramón Badorrey、Carlos Cativiela、Roberto Díez

  DOI：10.1055/s-2005-871534

  日期：——

  The first stereoselective synthesis of 1,4-dideoxy-1,4-imino-d-Talitol has been achieved in 24% overall yield from conveniently protected (S)-glyceraldimine (1), which is easily prepared from inexpensive d-mannitol. The synthesis is based on the addition of vinylmagnesium bromide to this N-benzylimine followed by N-acylation, ring-closing metathesis and asymmetric dihydroxylation. In this synthesis as many as three stereogenic centres are constructed with total stereoselectivity.

  1,4-二脱氧-1,4-亚氨基-D-塔利醇的首次立体选择性合成，从方便保护的（S）-甘油二胺（1）中获得了24%的总收率，而（S）-甘油二胺（1）很容易从廉价的D-甘露醇制备。该合成基于乙烯基溴化镁与N-苄基亚胺的加成，然后进行N-酰化、环化复分解和不对称二羟基化。在该合成中，多达三个立体中心以完全立体选择性构建。