2,3,4,6-tetrabenzyl-α-D-mannopyranosyl-(1->1)-2,3,4,6-tetrabenzyl-α-D-mannopyranoside | 25018-28-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetrabenzyl-α-D-mannopyranosyl-(1->1)-2,3,4,6-tetrabenzyl-α-D-mannopyranoside
• 英文别名: (2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside；(2R,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-2-(phenylmethoxymethyl)-6-[(2R,3S,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxane
• CAS: 25018-28-4；58781-26-3；58781-27-4；71748-32-8；74080-40-3；74080-43-6；74080-44-7；77943-36-3；95189-57-4；95189-58-5；103130-73-0；74080-41-4
• 化学式: C₆₈H₇₀O₁₁
• 分子量: 1063.3
• InChiKey: AVZQUDHQXONDDN-QAIPEPPASA-N

物化性质

• 熔点：
  121 °C
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11
• 重原子数：
  79
• 可旋转键数：
  28
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetrabenzyl-α-D-mannopyranosyl-(1->1)-2,3,4,6-tetrabenzyl-α-D-mannopyranoside 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 1-O-(α-D-mannopyranosyl)-α-D-mannopyranose
  参考文献：
  名称：

  新式合成糖苷。合成的α，α-海藻糖，类似物半乳糖，甘露等-α-d-糖苷

  摘要：

  摘要在三氟甲磺酸（三氟甲磺酸）酐为催化剂，二氯甲烷为溶剂的情况下，在低温下存在2,3,4,6-四-O-苄基-d-吡喃葡萄糖，2,3,4,6-四-O -苄基-d-吡喃半乳糖和2,3,4,6-四-O-苄基-d-甘露吡喃糖几乎定量地转化为相应的α，α-（1→1）和2：1混合物α，β-（1→1）二糖。因此，在柱后，获得了α，α-海藻糖的纯2,3,4,6,2'，3'，4'，6-辛基-O-苄基衍生物，以及d-半乳糖和d-甘露糖类似物。层析，产率55-65％。氢解得到相应的游离糖。以10–34％的产率获得纯的异头物。该方法的潜力通过合成2,3,4,6-四-O-苄基-α-d-吡喃葡萄糖基2,3：4,5-二-O-异亚丙基-β-d-果糖吡喃糖苷来证明。 50％的产量，

  DOI：

  10.1016/s0008-6215(00)85133-2
• 作为产物：
  描述：

  2-allylphenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 在 sodium methylate 、 silver trifluoromethanesulfonate 、 一氯化碘 、 sodium hydride 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 14.0h， 生成 2,3,4,6-tetrabenzyl-α-D-mannopyranosyl-(1->1)-2,3,4,6-tetrabenzyl-α-D-mannopyranoside
  参考文献：
  名称：

  2-Allylphenyl glycosides as glycosyl donors for sugar coupling

  摘要：

  Glycosylations employing 2-allylphenyl glycoside, a new type of stable glycosyl donor, were optimized and explored with a variety of acceptors promoted by ICl/AgOTf. The utility of the protocol was further demonstrated with an efficient synthesis of the disaccharide fragment of bleomycins. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.01.022

文献信息

• Synthesis of Methyl<i>O</i>-<i>α</i>-D-Mannosyl-(1→4)-[(3-<i>O</i>-methyl-<i>α</i>-D- mannosyl)-(1→4)-]_<i>n</i>3-<i>O</i>-methyl-<i>α</i>-D-mannosides (<i>n</i>= 0, 1, and 2) via Dehydrative Glycosylation
  作者：Motoko Hirooka、Megumi Terayama、Emi Mitani、Shinkiti Koto、Asako Miura、Kayo Chiba、Ayano Takabatake、Takako Tashiro

  DOI：10.1246/bcsj.75.1301

  日期：2002.6

  Methyl O-α-D-mannopyranosyl-(1→4)-[(3-O-methyl-α-D-mannopyranosyl-(1→4)-]n3-O-methyl-α-D-mannopyranosides (n = 0, 1, and 2), the lowest homologs related to the 3-O-methylmannose polysaccharides (MMP) from Mycobacterium smegmatis, were synthesized via dehydrative glycosylation reactions. The reagent systems, composed of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, and triethylamine, of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, and 1, 8-diazabicyclo[5.4.0]undec-7-ene, and of trimethylsilyl trifuloromethanesulfonate and pyridine were useful.

  通过脱水糖基化反应合成了甲基 O-α-D-吡喃甘露糖基-(1→4)-[(3-O-甲基-α-D-吡喃甘露糖基-(1→4)-]n3-O-甲基-α-D-吡喃甘露糖苷（n = 0、1 和 2），这是分枝杆菌中 3-O-甲基甘露糖多糖（MMP）的最低同源物。由对硝基苯磺酰氯、三氟甲磺酸银和三乙胺，对硝基苯磺酰氯、三氟甲磺酸银和 1，8-二氮杂双环[5.4.0]十一-7-烯，以及三氟甲磺酸三甲基硅酯和吡啶组成的试剂体系非常有用。
• THE HIGHLY STEREOSELECTIVE SYNTHESIS OF PERBENZYLATED α,α-TREHALOSE AND ITS D-<i>GALACTO</i>AND D-<i>MANNO</i>ANALOGS
  作者：Juji Yoshimura、Kazutoshi Hara、Tatsuya Sato、Hironobu Hashimoto

  DOI：10.1246/cl.1983.319

  日期：1983.3.5

  6-tetra-o-benzyl-1-o-trimethylsilyl-α,β-D-glucopyranose in dichloromethane with trimethylsilyl triflate catalyst gave the corresponding α,α- and α,β-trehaloses in quantitative yield. A similar treatment of D-galacto and D-manno analogs gave exclusively the corresponding α,α-anomers, respectively.

  用三甲基甲硅烷基三氟甲磺酸酯催化剂在二氯甲烷中处理 2,3,4,6-四-邻苄基-1-邻三甲基甲硅烷基-α,β-D-吡喃葡萄糖，定量得到相应的α,α-和α,β-海藻糖屈服。D-半乳糖和 D-甘露糖类似物的类似处理分别只产生相应的 α,α-异头物。
• 2-Allyloxyphenyl glycoside as a new and stable type of glycosyl donors
  作者：Jinq-Chyi Lee、Guan-Rong Pan、Suvarn S. Kulkarni、Shun-Yuan Luo、Chun-Chen Liao、Shang-Cheng Hung

  DOI：10.1016/j.tetlet.2005.12.127

  日期：2006.3

  A high-yielding coupling of a new and stable type of glycosyl donors, namely 2-allyloxyphenyl glycoside, with a variety of alcohols via NIS/TfOH reagent combination as effective activators at room temperature is described here. (c) 2006 Elsevier Ltd. All rights reserved.
• Rational Design and Synthesis of a 1,1-Linked Disaccharide That Is 5 Times as Active as Sialyl Lewis X in Binding to E-Selectin
  作者：Kazumi Hiruma、Tetsuya Kajimoto、Gabriel Weitz-Schmidt、Ian Ollmann、Chi-Huey Wong

  DOI：10.1021/ja9611093

  日期：1996.1.1

  We describe here a rational design and synthesis of (3-O-carboxymethyl)-beta-D-galactopyranosyl alpha-D-mannopyranoside which is 5 times as active as sialyl Lewis X in binding to E-selectin and also effective against P- and L-selectin. A new method for the 1,1-glycosidic bond formation via coupling of protected trimethylsilyl beta-D-galactoside and alpha-mannosyl fluoride in the presence of BF3 . Et(2)O is described.
• Sulfoxide Covalent Catalysis: Application to Glycosidic Bond Formation
  作者：Timothy A. Boebel、David Y. Gin

  DOI：10.1002/anie.200352761

  日期：2003.12.8