1,2,6-三-O-乙酰基-3,4-二-O-苄基吡喃己糖 | 65827-57-8

• 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
• 中文名称: 1,2,6-三-O-乙酰基-3,4-二-O-苄基吡喃己糖
• 英文名称: 1,2,6-tri-O-acetyl-3,4-di-O-benzyl-α-D-mannopyranose
• 英文别名: 1,2,6-Tri-O-acetyl-3,4-di-O-benzyl-D-mannopyranose；1,2,6-Tri-O-acetyl-3,4-di-O-benzyl-a-D-mannopyranose；[(2R,3R,4S,5S,6R)-5,6-diacetyloxy-3,4-bis(phenylmethoxy)oxan-2-yl]methyl acetate
• CAS: 65827-57-8
• 化学式: C₂₆H₃₀O₉
• 分子量: 486.519
• InChiKey: NBSOZVWQAKGBSC-JMTTVTNBSA-N

物化性质

• 熔点：
  73-75°C
• 溶解度：
  可溶于二氯甲烷、乙醚、乙酸乙酯、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  35
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1,2,6-三-O-乙酰基-3,4-二-O-苄基吡喃己糖 在 溴化钛(IV) 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 2.5h， 以96%的产率得到2,6-di-O-acetyl-3,4-di-O-benzyl-α-D-mannopyranosyl bromide
  参考文献：
  名称：

  合成烯类N-乙酰神经氨酸盐-合成氢嵌段。Kupplung zum N-乙酰神经氨酸半透明糖蜜三甲基甲硅烷基三氟甲磺酸

  摘要：

  摘要获得了由N-乙酰神经氨酸和乳糖胺组成的三糖合成嵌段，该嵌段可与其他糖单元进行一般偶联反应。O-（5-乙酰氨基-4,7,8,9-四-甲基-O-乙酰基-3,5-二脱氧-α-和-β-d-甘油-d-半乳清-2-壬基吡喃二磺酸酯）-（2→ 6）-O-（2,3,4-三-O-乙酰基-β-d-吡喃半乳糖基）-（1→4）-1,3,6-三-O-乙酰基-2-脱氧-2-邻苯二甲酰亚胺基-β-d-吡喃葡萄糖被用作糖基供体。在三甲基甲硅烷基三氟甲基磺酸盐的存在下，通过与在OH-2处代表糖基受体的未取代的d-甘露糖衍生物反应，将两种化合物转化为四糖。除去保护基团得到O-（5-乙酰氨基-3，

  DOI：

  10.1016/s0008-6215(00)90670-0
• 作为产物：
  描述：

  1,2-O-(1-methoxyethylidene)-6-O-trityl-β-D-mannopyranose 在 硫酸 、 sodium hydride 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.5h， 生成 1,2,6-三-O-乙酰基-3,4-二-O-苄基吡喃己糖
  参考文献：
  名称：

  稻瘟病菌细胞壁蛋白杂多糖内链模型的合成：支链d-甘露糖苷

  摘要：

  摘要描述了高效合成支链d-甘露糖苷甲基2,6-di-O-（2-O-α-d-甘露吡喃糖基-α-d-甘露吡喃糖基）α-d-甘露吡喃糖苷和甲基2,4-二- O-（2-O-α-d-甘露吡喃糖基-α-d-甘露吡喃糖基）-α-d-甘露吡喃糖苷，起始于糖基受体甲基3,4-二-O-苄基-α-d-甘露吡喃糖苷和甲基3 ，6-二-O-苄基-α-d-甘露吡喃糖苷，并使用保护的d-甘露糖苷甲基3,4-二-O-苄基-2,6-二-O-（3,4,6-tri- O-苄基-α-d-甘露吡喃糖基）-α-d-甘露糖吡喃糖苷和甲基3,6-二-O-苄基-2,4-二-O-（3,4,6-三-O-苄基- α-d-甘露糖吡喃糖基）-α-d-甘露糖吡喃糖苷为关键中间体。

  DOI：

  10.1016/s0008-6215(00)80753-3

文献信息

• One-pot synthesis of branched oligosaccharides by use of galacto- and mannopyranosyl thioglycoside diols as key glycosylating agents
  作者：Xing-Yong Liang、Qiang-Wei Liu、Hua-Chao Bin、Jin-Song Yang

  DOI：10.1039/c3ob40421h

  日期：——

  one-pot synthesis of three fully protected oligosaccharides 22, 36, and 50 with di-branched structures by employing D-galacto- and mannopyranosyl thioglycoside diols as central glycosylating agents. After global deprotection, they were converted respectively into the 3-aminopropyl linker-containing free oligosaccharide fragments 14, 24, and 38 structurally related to cell wall oligosaccharides from Atractylodes

  我们描述在本文中的高效的四组分一锅合成的三个完全受保护的低聚糖22，36，和50与二支化结构通过采用d -galacto-和吡喃甘露糖基硫代糖苷二醇中央糖基化剂。完全脱保护后，将它们分别转化成3-氨基丙基含有接头-自由寡糖片段14，24，和38结构上与细胞壁寡糖从苍术DC，海洋真菌Lineolata rhizophorae和致病结核分枝杆菌。异头碳原子上的3-氨基丙基接头可使这些合成的低聚物与合适的蛋白质载体缀合。
• Combination of solid phase and solution phase synthesis of oligosaccharides using sonication
  作者：Christabel T. Tanifum、Jianjun Zhang、Cheng-Wei T. Chang

  DOI：10.1016/j.tetlet.2010.06.027

  日期：2010.8

  An approach that combines solid phase and solution phase synthesis of oligosaccharides via the assistance of sonication has been developed. By employing the traceless linker, the designed oligosaccharides can be obtained in pure form and, more importantly, ready for incorporation to aglycons of interest via ‘Click’ chemistry or amide linkage. The overall strategy will facilitate the studies of roles

  已经开发了通过超声处理结合寡糖的固相和溶液相合成的方法。通过使用无痕连接子，可以以纯净形式获得设计的寡糖，更重要的是，可以通过“点击”化学或酰胺键将寡糖掺入目标糖苷。总体策略将有助于研究碳水化合物在生物活性化合物中的作用。
• Synthesis of a nona- and an undeca-saccharide that form part of the complex type of carbohydrate moiety of glucoproteins
  作者：Hans Lönn、Jörgen Lönngren

  DOI：10.1016/0008-6215(83)88003-3

  日期：1983.8

  Silver trifluoromethanesulfonate-promoted condensation of 3,6-di-O-acetyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-acetyl-beta-D- galactopyranosyl)-beta-D-glucopyranosyl bromide with benzyl 2,4,-di-O-benzyl-6-O-(3,4-di-O-benzyl-alpha-D-mannopyranosyl)-3-O-(3,6-di-O- benzyl-alpha-D-mannopyranosyl)-alpha-D-mannopyranoside gave nonasaccharide and undecasaccharide derivatives. The nonasaccharide 2 and

  三氟甲磺酸银促进的3,6-二-O-乙酰基-2-脱氧-2-邻苯二甲酰亚胺基-4-O-（2,3,4,6-四-O-乙酰基-β-D-吡喃半乳糖基）缩合β-D-吡喃葡萄糖基溴与苄基2,4，-二-O-苄基-6-O-（3,4-二-O-苄基-α-D-甘露吡喃糖基）-3-O-（3,6-二-O-苄基-α-D-甘露吡喃糖基）-α-D-甘露吡喃糖苷得到九糖和十一糖衍生物。通过除去保护基，然后进行N-乙酰化，得到九糖2和十一糖3。（公式；请参见文字）。
• Studies on carbohydrates XX. Synthesis of hexasaccharide containing lactosamine unit using glycosyl trichloroacetates as glycosyl donors
  作者：Xiao Xiang Zhu、Ping Yu Ding、Meng Shen Cai

  DOI：10.1016/0040-4039(96)01989-2

  日期：1996.11

  O-Glycosyl trichloroacetate, a stable and readily obtained intermediate, was activated as a highly reactive glycosyl donor upon treatment with acid and coupled with the acceptor to afford complex glycosides with high stereoselectivity.

  稳定且易于获得的中间体O-糖基三氯乙酸酯，经酸处理后被活化为高反应性糖基供体，并与受体偶联，从而提供了具有高立体选择性的复合糖苷。
• Synthesis of α-D-Glucopyranosyl-(1-3)-α-D-Mannopyranosyl-(1-7)-4-Methylumbelliferone, A Fluorogenic Substrate for Endo-α-1,2-Mannosidase
  作者：C. Vogel、G. Pohlentz

  DOI：10.1080/07328300008544148

  日期：2000.1.1

  alpha -D-Glucopyranosyl-(1-3)-alpha -D-mannopyranosyl-(1-7)-4-methylumbelliferone (Glc-Man-Muf) was synthesized as a potential fluorogenic substrate for endo-alpha -1,2-mannosidase. The synthesis was designed in a convergent way. The glucose donor ethyl 2,3,4,6-tetra-O-benzyl-1-thio-beta -glucopyranoside and the mannose acceptor 1,2:4,6-di-O-isopropylidene-beta -mannopyranose were coupled in the presence of N-iodosuccinimide and trifluoromethanesulfonic acid to yield the corresponding disaccharide derivative. After conversion into peracetylated alpha -D-glucopyranosyl-(1-3)-alpha -D-mannopyranose the disaccharide was attached to 4-methylumbelliferone using the Helferich method. After separation of the desired isomer, deacetylation yielded the title compound. Glc-Man-Muf was used as st substrate in endomannosidase assays with rat liver Golgi preparations as an enzyme source (in the presence of the alpha -glucosidase inhibitor deoxynojirimycin). The degradation of Glc-Man-Muf was linear with protein up to 300 mug and with time up to 2 h. V-max and K-m were determined to be 0.17 nmol/mg x h and 3.7 mM, respectively.