(3R,4R,5S)-5-ethylpyrrolidine-3,4-diol | 759430-56-3

• 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: (3R,4R,5S)-5-ethylpyrrolidine-3,4-diol
• 英文别名: (2S,3R,4R)-2-ethylpyrrolidine-3,4-diol
• CAS: 759430-56-3
• 化学式: C₆H₁₃NO₂
• 分子量: 131.175
• InChiKey: DPKVFORGPDPGQG-KVQBGUIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  9
• 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：
  52.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,4R,5S)-5-ethylpyrrolidine-3,4-diol 在 2,4,6-三甲基吡啶 、 二叔丁基过氧化物 、 4 A molecular sieve 、 sodium methylate 、 silver trifluoromethanesulfonate 、 silver perchlorate 、 sodium carbonate 、 tin(IV) oxide 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 54.5h， 生成 4-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl-3-O-(β-D-galactopyranosyl)-(2S,3R,4R)-1-benzyloxycarbonyl-2-ethyl-3,4-dihydroxypyrrolidine
  参考文献：
  名称：

  Synthesis of A Novel Sialyl Lewis X Analogue Containing A Pyrrolidine in Place ofN-Acetyl Glucosamine

  摘要：

  The synthesis of the new sialyl Lewis X analogue, 4-O-(alpha-L-fucopyranosyl)-3-O-(3-O-sodium sulfonato-beta-D-galactopyranosyl)-(2S,3R, 4R)-2-ethyl-3,4-dihydroxypyrrolidine 2 has been achieved. The N-acetyl glucosamine unit of natural Lewis X has been replaced by a rigid 3R/4R-dihydroxylated pyrrolidine 12. This one has been synthezised from the methyl 4-O-benzoyl-2,3-di-O-benzyl-6-deoxy-6-iodo-alpha-D-altropyranoside sugar precursor 10 using the Ganem/Bernotas one-pot elimination-reductive amination ring contraction reaction. The (2S,3R,4R)-1-benzyloxycarbonyl-3,4-dihydroxy-2-ethylpyrrolidine 12 obtained was subsequently regioselectively glycosylated, using 2,3,4-tri-O-benzyl-alpha-L-fucopyranosyl fluoride and 2,3,4,6-tetra-O-benzoyl-beta-D-galactopyranosyl bromide as glycosyl donors. Disaccharide containing pyrrolidine 21 was finally transformed into the target O-sulfated analog 2, after regioselective sulfation and usual deprotection.

  DOI：

  10.1080/07328300008544095
• 作为产物：
  描述：

  (4aR,6S,7S,8S,8aS)-6-Methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol 在 palladium on activated charcoal 吡啶 、 咪唑 、 盐酸 、 氢氧化钾 、 氢气 、 碘 、 sodium cyanoborohydride 、 三苯基膦 、 锌 作用下， 以 甲醇 、 乙醇 、 水 、 甲苯 为溶剂， 反应 38.25h， 生成 (3R,4R,5S)-5-ethylpyrrolidine-3,4-diol
  参考文献：
  名称：

  Synthesis of A Novel Sialyl Lewis X Analogue Containing A Pyrrolidine in Place ofN-Acetyl Glucosamine

  摘要：

  The synthesis of the new sialyl Lewis X analogue, 4-O-(alpha-L-fucopyranosyl)-3-O-(3-O-sodium sulfonato-beta-D-galactopyranosyl)-(2S,3R, 4R)-2-ethyl-3,4-dihydroxypyrrolidine 2 has been achieved. The N-acetyl glucosamine unit of natural Lewis X has been replaced by a rigid 3R/4R-dihydroxylated pyrrolidine 12. This one has been synthezised from the methyl 4-O-benzoyl-2,3-di-O-benzyl-6-deoxy-6-iodo-alpha-D-altropyranoside sugar precursor 10 using the Ganem/Bernotas one-pot elimination-reductive amination ring contraction reaction. The (2S,3R,4R)-1-benzyloxycarbonyl-3,4-dihydroxy-2-ethylpyrrolidine 12 obtained was subsequently regioselectively glycosylated, using 2,3,4-tri-O-benzyl-alpha-L-fucopyranosyl fluoride and 2,3,4,6-tetra-O-benzoyl-beta-D-galactopyranosyl bromide as glycosyl donors. Disaccharide containing pyrrolidine 21 was finally transformed into the target O-sulfated analog 2, after regioselective sulfation and usual deprotection.

  DOI：

  10.1080/07328300008544095

文献信息

• Structure-Guided Engineering of <scp>D</scp> -Fructose-6-Phosphate Aldolase for Improved Acceptor Tolerance in Biocatalytic Aldol Additions
  作者：Anna Soler、Mariana L. Gutiérrez、Jordi Bujons、Teodor Parella、Cristina Minguillon、Jesús Joglar、Pere Clapés

  DOI：10.1002/adsc.201500073

  日期：2015.5.26

  structure‐guided redesign of D‐fructose‐6‐phosphate aldolase from Escherichia coli (FSA) was devised for improving the acceptor tolerance towards α‐substituted and conformationally constrained aldehydes. FSA A129S/R134X/A165G/S166G and L107Y/A129G/R134X/A165G/S166G variants, where X was R, V, P, or S, were the most suited biocatalysts for dihydroxyacetone, hydroxyacetone and glycolaldehyde additions to 20 α‐substituted

  为提高受体对α-取代的和构象受限的醛的耐受性，设计了来自大肠杆菌（FSA）的D-果糖-6-磷酸醛缩酶醛缩酶的结构指导的重新设计。FSA A129S / R134X / A165G / S166G和L107Y / A129G / R134X / A165G / S166G变体，其中X为R，V，P或S，是向20个α-取代的N加成二羟基丙酮，羟丙酮和乙醇醛的最合适生物催化剂。-Cbz-氨基醛（Cbz =苄氧羰基），包括吡咯烷和哌啶衍生物。对于全动态立体控制SI -SI面加入醛缩酶-结合的亲核试剂到的Ñ观察-CBZ-氨基醛羰基，家具相应d -苏式配置羟醛加合物> 95:5博士通过NMR评估的。还原胺化后，鉴定并表征了47种不同的亚氨基环醇。在一些实施例中，观察到相应醛的部分外消旋化，这似乎主要在醛醇加成反应期间产生。
• Synthesis of A Novel Sialyl Lewis X Analogue Containing A Pyrrolidine in Place of<i>N</i>-Acetyl Glucosamine
  作者：Elsa Dechaux、Pascal Savy、Samule Bouyain、Claude Monneret、Jean-Claude Florent

  DOI：10.1080/07328300008544095

  日期：2000.1

  The synthesis of the new sialyl Lewis X analogue, 4-O-(alpha-L-fucopyranosyl)-3-O-(3-O-sodium sulfonato-beta-D-galactopyranosyl)-(2S,3R, 4R)-2-ethyl-3,4-dihydroxypyrrolidine 2 has been achieved. The N-acetyl glucosamine unit of natural Lewis X has been replaced by a rigid 3R/4R-dihydroxylated pyrrolidine 12. This one has been synthezised from the methyl 4-O-benzoyl-2,3-di-O-benzyl-6-deoxy-6-iodo-alpha-D-altropyranoside sugar precursor 10 using the Ganem/Bernotas one-pot elimination-reductive amination ring contraction reaction. The (2S,3R,4R)-1-benzyloxycarbonyl-3,4-dihydroxy-2-ethylpyrrolidine 12 obtained was subsequently regioselectively glycosylated, using 2,3,4-tri-O-benzyl-alpha-L-fucopyranosyl fluoride and 2,3,4,6-tetra-O-benzoyl-beta-D-galactopyranosyl bromide as glycosyl donors. Disaccharide containing pyrrolidine 21 was finally transformed into the target O-sulfated analog 2, after regioselective sulfation and usual deprotection.