6-O-acetyl-2,3,4-tri-O-benzoyl-α-D-galactopyranosyl trichloroacetimidate | 363619-57-2

• 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: 6-O-acetyl-2,3,4-tri-O-benzoyl-α-D-galactopyranosyl trichloroacetimidate
• 英文别名: Bz(-2)[Bz(-3)][Bz(-4)]Gal6Ac(a)-O-C(NH)CCl3；[(2R,3S,4S,5R,6R)-2-(acetyloxymethyl)-4,5-dibenzoyloxy-6-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl] benzoate
• CAS: 363619-57-2
• 化学式: C₃₁H₂₆Cl₃NO₁₀
• 分子量: 678.907
• InChiKey: LMPRSGVCSGTWDZ-MOHFTYJVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  45
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  148
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  6-O-acetyl-2,3,4-tri-O-benzoyl-α-D-galactopyranosyl trichloroacetimidate 在 2,4,6-三甲基吡啶 、 4-二甲氨基吡啶 、 三甲基溴硅烷 、 三氟甲磺酸三甲基硅酯 、 4 Angstroem MS 、 高氯酸,吡啶 作用下， 以 吡啶 、 甲醇 、 硝基甲烷 、 二氯甲烷 、 乙腈 为溶剂， 反应 15.0h， 生成 [(2S,3S,4S,5R,6R)-5-[(2S,3R,4S,5S,6R)-6-(acetyloxymethyl)-3,4,5-tribenzoyloxyoxan-2-yl]oxy-3,4-dibenzoyloxy-6-(benzoyloxymethyl)oxan-2-yl]methylphosphonic acid
  参考文献：
  名称：

  Synthesis of β-d-Galp-(1→4)-α-d-Manp methanephosphonate, a substrate analogue for the elongating α-d-mannosyl phosphate transferase in the Leishmania

  摘要：

  An isosteric C-glycoside phosphono analogue of dec-9-enyl beta -D-galactopyranosyl-(1 -->4)-alpha -D-mannopyranosyl phosphate was synthesised and showed high biological activity in the Leishmania MPT assay. A one-step Horner-Emmons/Michael reaction was developed for the stereoselective preparation of cc-D-mannosyl methanephosphonate derivatives. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00961-3
• 作为产物：
  描述：

  [(2R,3S,4S,5R)-6-acetyloxy-2-(acetyloxymethyl)-4,5-dibenzoyloxyoxan-3-yl] benzoate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 苄胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 29.0h， 生成 6-O-acetyl-2,3,4-tri-O-benzoyl-α-D-galactopyranosyl trichloroacetimidate
  参考文献：
  名称：

  An Efficient Method for the Synthesis of 2,6-Branched Galacto-Oligo­saccharides and Its Applications to the Synthesis of Three Tetrasaccharides and a Hexasaccharide Related to the Arabinogalactans (AGs)

  摘要：

  通过使用6-O-Ac-2,3,4-三-O-Bz-α-d-半乳糖吡喃糖苷三氯乙酰亚胺、2,6-二-O-Ac-3,4-二-O-Bz-α-d-半乳糖吡喃糖苷三氯乙酰亚胺和2-O-Ac-3,4,6-三-O-Bz-α-d-半乳糖吡喃糖苷三氯乙酰亚胺作为合成砌块，开发了一种高效合成2,6-支化半乳寡糖的方法。利用这种方法，可以方便地制备与植物来源的AGs相关的三种四糖和一种六糖。

  DOI：

  10.1055/s-2003-42109

文献信息

• A concise synthesis of arabinogalactan with β-(1→6) galactopyranose backbone and α-(1→2) arabinofuranose side chains
  作者：Ying Zeng、Aixiao Li、Fanzuo Kong

  DOI：10.1016/j.tetlet.2003.08.087

  日期：2003.11

  Penta- and octasaccharides composed of β-(1→6)-linked galactose backbone with α-(1→2)-linked arabinose branches were synthesized through coupling of α-(1→5)-linked arabinofuranosyl disaccharide donor with a tri- and tetrasaccharide backbone at C-2, respectively.

  通过将α-（1→5）连接的阿拉伯呋喃糖基二糖供体与三-α-（1→5）连接的阿拉伯呋喃糖基二糖供体偶联，合成由β-（1→6）连接的半乳​​糖骨架和α-（1→2）连接的阿拉伯糖支组成的五糖和八糖。 C-2分别为四糖主链和四糖主链。
• Syntheses of β-(1→6)-branched β-(1→3)-linked d-galactans that exist in the rhizomes of Atractylodes lancea DC
  作者：Aixiao Li、Fanzuo Kong

  DOI：10.1016/j.carres.2005.05.017

  日期：2005.9

  β-(1→6)-linked disaccharide donor 4 . Condensation of 2 with 5 and subsequent selective deacetylation by methanolysis produced the β-(1→6)-linked disaccharide acceptor 7 . Reaction of 7 with 4 , oxidative cleavage of 1-OMP, and trichloroacetimidate formation produced the tetrasaccharide donor 9 . The penta- ( 15 ), the hexa- ( 17 ), and the heptasaccharide donor 19 were synthesized similarly. Meanwhile

  摘要用2,3,4,6-四-O-苯甲酰基-α-d-吡喃半乳糖基三氯乙酰亚氨酸酯（1 ），4-甲氧基苯基2,3,4-三-O-苯甲酰基-β-d-吡喃半乳糖苷（2），6-O-乙酰基-2,3,4-三-O-苯甲酰基-α-d-吡喃半乳糖基三氯乙酰亚氨酸（5），4-甲氧基苯基6-O-乙酰基-2,4-二-O-苯甲酰基-β-d-吡喃半乳糖苷（22）和4-甲氧基苯基2,4,6-三-O-苯甲酰基-β- d-半乳糖吡喃糖苷（26）为关键合成子。将2与1偶联，然后将1-OMP氧化裂解，随后形成三氯乙酰亚氨酸酯，得到β-（1→6）连接的二糖供体4。2与5的缩合以及随后的甲醇解选择性脱乙酰基产生了β-（1→6）连接的二糖受体7。7与4的反应，1-OMP的氧化裂解和三氯乙亚氨酸盐的生成产生了四糖供体9。相似地合成五（15），六（17）和七糖供体19。同时，用22处理1产生β-（1→3）-连接的二糖23和α-（1→3）-连接
• Syntheses of arabinogalactans consisting of β-(1→6)-linked d-galactopyranosyl backbone and α-(1→3)-linked l-arabinofuranosyl side chains
  作者：Aixiao Li、Fanzuo Kong

  DOI：10.1016/j.carres.2004.05.007

  日期：2004.8

  nonasaccharides, β- d -Gal p -(1 → 6)-[α- l -Ara f -(1 → 3)]-β- d -Gal p -(1 → 6)-β- d -Gal p -(1 → 6)-β- d -Gal p -(1 → 6)-[α- l -Ara f -(1 → 5)-α- l -Ara f -(1 → 3)]-β- d -Gal p -(1 → 6)-β- d -Gal p and β- d -Gal p -(1 → 6)-[α- l -Ara f -(1 → 5)-α- l -Ara f -(1 → 3)]-β- d -Gal p -(1 → 6)-β- d -Gal p -(1 → 6)-β- d -Gal p -(1 → 6)-[α- l -Ara f -(1 → 3)]-β- d -Gal p -(1 → 6)-β- d -Gal p , were synthesized

  5-三-O-苯甲酰基-α-1-阿拉伯呋喃糖基三氯乙酰亚胺酸酯（8）和​​2,3,5-三-O-苯甲酰基-α-1-α-阿拉伯呋喃糖基-（1→5）-2,3-二-O -关键的合成子是-苯甲酰基-α-1-阿拉伯呋喃糖基三氯乙酰亚氨酸盐（11）。基于这些合成子，通过简单的转化合成了四（10）和五糖供体（13），以及四（20）和五糖受体（22）。22与10的偶联，以及20与13的偶联以及随后的脱酰作用，分别得到九糖24和26，由β-（1→6）-连接的吡喃木糖基主链和α-（1→3）-连接的阿拉伯呋喃糖基侧链组成。不同的大小。根据这些合成子，通过简单的转化合成了四（20）和五糖受体（22）。22与10的偶联，以及20与13的偶联以及随后的脱酰作用，分别得到九糖24和26，由β-（1→6）-连接的吡喃木糖基主链和α-（1→3）-连接的阿拉伯呋喃糖基侧链组成。不同的大小。根据这些合成子，通过简单的转化合成了四（
• HClO4–SiO2 catalyzed glycosylation using sugar trichloroacetimidates as glycosyl donors
  作者：Yuguo Du、Guohua Wei、Shuihong Cheng、Yuxia Hua、Robert J. Linhardt

  DOI：10.1016/j.tetlet.2005.11.025

  日期：2006.1

  Silica-supported perchloric acid (HClO4-SiO2) has been used as an efficient promoter,, as a replacement of TMSOTf, in various glycosylation reactions using sugar trichloroacetimidates as glycosyl donors. Operational simplicity, economic considerations, high yield, short reaction time and low toxicity were the key features associated with this protocol. (c) 2005 Elsevier Ltd. All rights reserved.
• Concise syntheses of arabinogalactans with β-(1→6)-linked galactopyranose backbones and α-(1→3)- and α-(1→2)-linked arabinofuranose side chains
  作者：Aixiao Li、Fanzuo Kong

  DOI：10.1016/j.bmc.2004.10.035

  日期：2005.2

  4-Methoxyphenyl glycosides of 2,3"-bis-alpha-L-arabinofuranosyl branched beta-D-(1-6)-linked galactopyranosyl tetraose (16), 3',2""-bis-alpha-L-arabinofuranosyl branched beta-D-(1-->6)-linked Plactopyranosyl hexaose (27), and a twentyose (42) consisting of beta- (1-->6)-linked D-galactopyranosyl pen tadecaoligosaccha ride backbone with alpha-L-arabinofuranosyl side chains alternatively attached at C-2 and C-3 of the middle galactose residue of each consecutive beta-(1-->6)-linked galactotriose unit of the backbone. were synthesized with isopropyl 3-O-allyl-2.4-di-O-benzoyl-1-thio-beta-D-galactopyranoside (6). 2.3.4.6-tetra-O-benzoyl-alpha-D-galactopyranosyl trichloroacetimidate (7), 2,.3,5-tri-O-benzoyl-alpha-L-arabinofuranosyl trichloroacetimidate (12), 6-O-acetyl-2,3,4-tn-O-benzoyl-alpha-D-galactopyranosyl trichloroacetimidate (17), 4-methoxyphenyl 2,3,4-tri-O-benzo-beta-D-galactopyranoside (19), and 2,6-di-O-acetyl-3,4-di-O-benzoyl-alpha-D-galactopyranosyl trichloroacetimidate (28) as the key synthons. Condensation of 6 with 7 gave the disaccharide donor 8, and subsequent condensation of 8 with 4-methoxyphenyl 2.3.4-tri-O-benzoyl-beta-D-galactopyranosyl-(1-->6)-2-O-acetyl-3,4-di-O-benzoyl-beta-D-galactopyranoside (9) followed by selective deacetylation afforded the tetrasaccharide acceptor 11. Coupling of I I with 12 gave the pentasaccharide 13, its deallylation followed by coupling with 12. and debenzoylation Rave the hexasaccharide 16 with beta-(1-->6)-linked galactopyranose backbone and 2- and 3"-linked alpha-L-arabinofuranose side chains. The octasaccharide 27 was similarly synthesized, while the twentyoside 42 was synthesized with tetrasaccharides 33 or 24 as the donors and 23, 36, 38, and 40 as the acceptors by consecutive couplings followed by deacylation. (C) 2004 Elsevier Ltd. All rights reserved.