3-chloro-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)benzylideneamine | 121839-50-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-chloro-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)benzylideneamine
• 英文别名: [(2R,3S,4S,5R,6R)-6-[(E)-(3-chlorophenyl)methylideneamino]-3,4,5-tris(2,2-dimethylpropanoyloxy)oxan-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 121839-50-7
• 化学式: C₃₃H₄₈ClNO₉
• 分子量: 638.198
• InChiKey: HUTVVJMTNHDUGO-ZYRFJDCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  44
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  127
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3-chloro-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)benzylideneamine 生成 [(2R,3S,4S,5R,6R)-6-[[(S)-(3-chlorophenyl)-cyanomethyl]amino]-3,4,5-tris(2,2-dimethylpropanoyloxy)oxan-2-yl]methyl 2,2-dimethylpropanoate
  参考文献：
  名称：

  KUNZ, HORST;SAGER, WILFRIED;PFRENGLE, WALDEMAR;SCHANZENBACH, DIRK, TETRAHEDRON LETT., 29,(1988) N 35, C. 4397-4400

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2,3,4,6-penta-O-pivaloyl-β-D-galactopyranose 在 镍 叠氮基三甲基硅烷 、 氢气 、 四氯化锡 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 3-chloro-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)benzylideneamine
  参考文献：
  名称：

  Kunz, Horst; Sager, Wilfried; Schanzenbach, Dirk, Liebigs Annalen der Chemie, 1991, # 7, p. 649 - 654

  摘要：

  DOI：

文献信息

• High diastereoselective vinylogous Mannich reaction induced by O-pivaloylated d-galactosylamine as the chiral auxiliary: stereoselective synthesis of 8-arylazocan-2-one
  作者：Bing Cui、Gang Hou、Yan Cai、Zhiwei Miao

  DOI：10.1016/j.carres.2013.03.020

  日期：2013.6

  The diastereospecific formation of β-N-glycosidically linked α,β-unsaturated δ-amino aldehyde derivatives has been achieved with high yield via a vinylogous Mannich reaction. The reaction was performed by using a O-pivaloylated galactosyl amine as a chiral template and AlCl3 as a promoter in THF. (S)-8-(p-Nitrophenyl) azocan-2-one can be stereoselective synthesized from (S) ethyl 7-galactosylamino

  β-N-糖苷键连接的α，β-不饱和δ-氨基醛衍生物的非对映异构形成已通过乙烯基曼尼希反应以高收率实现。该反应通过在THF中使用O-聚乙烯醇化的半乳糖胺作为手性模板并且使用AlCl 3作为促进剂来进行。（S）-8-（对硝基苯基）偶氮烷-2-酮可通过双键的连续加氢反应从（S）7-半乳糖基氨基-7-（对硝基苯基）庚-2,4-二烯酸酯中立体合成，环内酰胺的形成，以及在碱性条件下去除N-糖苷助剂的过程。
• Kunz, Horst; Schanzenbach, Dirk, Angewandte Chemie, 1989, vol. 101, # 8, p. 1042 - 1043
  作者：Kunz, Horst、Schanzenbach, Dirk

  DOI：——

  日期：——
• Carbohydrates as chiral templates: diastereoselective synthesis of N-glycosyl-N-homoallylamines and .beta.-amino acids from imines
  作者：Sabine Laschat、Horst Kunz

  DOI：10.1021/jo00020a033

  日期：1991.9

  Complexing properties and chirality of carbohydrates were utilized in diastereoselective reactions of O-pivaloylated N-galactosylimines with allylsilanes and -stannanes. With allyltrimethylsilane in the presence of SnCl4, imines 2 of aromatic and heteroaromatic aldehydes were converted to homoallylamines 3, giving ratios of diastereomers higher than 7:1. No addition products derived from alpha-anomeric aromatic imines were formed. Aliphatic homoallylamines 3 were synthesized by using allyltributylstannane in the presence of SnCl4. Both alpha- and beta-anomeric aliphatic imines reacted with the allylstannane. They gave the same ratio of diastereomers and showed the same sense of asymmetric induction.
• Asymmetric Mannich Synthesis ofβ-Amino Acids with Two New Stereogenic Centers at theα andβ Positions
  作者：Horst Kunz、Andreas Burgard、Dirk Schanzenbach

  DOI：10.1002/anie.199703861

  日期：1997.3.3
• Reversal of asymmetric induction in stereoselective strecker synthesis on galactosyl amine as the chiral matrix
  作者：Horst Kunz、Wilfried Sager、Waldemar Pfrengle、Dirk Schanzenbach

  DOI：10.1016/s0040-4039(00)80504-3

  日期：1988.1