N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)benzylideneamine | 121732-95-4

• 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: N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)benzylideneamine
• 英文别名: [(2R,3S,4S,5R,6R)-6-[(E)-benzylideneamino]-3,4,5-tris(2,2-dimethylpropanoyloxy)oxan-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 121732-95-4
• 化学式: C₃₃H₄₉NO₉
• 分子量: 603.753
• InChiKey: OXFDLHMJAQWGPR-LOWWOIKVSA-N

物化性质

• 沸点：
  614.8±55.0 °C(predicted)
• 密度：
  1.11±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  43
• 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：

  N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)benzylideneamine 在 zinc(II) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 生成
  参考文献：
  名称：

  邻氨基苯甲酸酯化的D-半乳糖胺作为手性助剂的立体选择性合成α-氨基（苯基）甲基（苯基）次膦酸

  摘要：

  通过Mannich型反应可以高收率实现β- N-糖苷连接的α-氨基膦酸衍生物的非对映异构形成。通过使用邻氨基苯甲酸酯化的半乳糖胺作为手性模板，使用SnCl 4作为促进剂在THF中进行反应（参见方案）。

  DOI：

  10.1002/chem.200901419
• 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 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。
• Stereoselective Synthesis of 2-Substituted Pyrrolidines
  作者：Sandrine Deloisy、Heiko Tietgen、Horst Kunz

  DOI：10.1135/cccc20000816

  日期：——

  Using O-pivaloyl protected D-galactopyranosylamine and D-arabinopyranosylamine, (S) or (R) configured α-substituted homoallylamines are synthesized with high diastereoselectivity by reaction of the corresponding aldimines with allyltributylstannane. Electrophile-induced endo-trig-cyclization of these N-glycosylhomoallylamines gave the 2-substituted pyrrolidines of high diastereomeric purity.

  使用O-皮瓦洛伊保护的D-半乳糖胺和D-阿拉伯糖胺，通过相应的醛亚胺与丁基三丁基基锡烯基反应，高对映选择性地合成了（S）或（R）配置的α-取代的同烯基胺。这些N-糖基同烯基胺的亲电诱导的内三角环化反应产生了高对映纯度的2-取代吡咯烷。
• Diastereoselective Synthesis of Adjacent P,C-Stereogenic β-<i>N</i>-Glycosidic Linked α-Aminophosphinates
  作者：Shuang Liu、Yuming Li、Zhiyu Yin、Qiuli Yu、Zhiwei Miao

  DOI：10.1021/acs.joc.6b02877

  日期：2017.3.3

  of adjacent P,C-stereogenic β-N-glycosidic linked α-aminophosphinates is developed in high yields via a phospha-Mannich reaction. The reaction was performed by employing (Rp)-O-(−)-menthyl H-phenylphosphinate and O-pivaloylated N-galactosylimine for double stereodifferentiation and BF3·Et2O as a promoter in THF. O-Pivaloylated N-galactosylphenyl imine 2 and (Rp)-O-(−)-menthyl H-phenylphosphinate 1 were

  通过膦-曼尼希反应以高收率开发了相邻的P，C-立体异构的β- N-糖苷连接的α-氨基次膦酸酯的非对映选择性形成。将反应物通过采用进行（[R p） - Ö - （ - ） -薄荷基ħ -phenylphosphinate和ö -pivaloylated Ñ -galactosylimine双stereodifferentiation和BF 3 ·的Et 2 O作为在THF中的启动子。O-聚乙烯基化的N-半乳糖基苯基亚胺2和（R p）-O -（-）-薄荷基H-苯基次膦酸酯1将其以非对映异构体比例高达20：1转化为N-半乳糖基α-氨基烷基次膦酸酯3。转化的合成方法提供了快速接近相邻的P，C-立体异构手性α-氨基次膦酸酯的途径。
• 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.