2',2'',3,3',3'',4'',6,6',6''-nona-O-acetyl-D-maltotrial | 183852-94-0

• 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: 2',2'',3,3',3'',4'',6,6',6''-nona-O-acetyl-D-maltotrial
• 英文别名: nona-O-acetyl-maltotrial；3,6,2',3',6',2'',3'',4'',6''-nona-O-acetylmaltotrial；[(2R,3S,4R)-4-acetyloxy-3-[(2R,3R,4S,5R,6R)-3,4-diacetyloxy-6-(acetyloxymethyl)-5-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 183852-94-0
• 化学式: C₃₆H₄₈O₂₃
• 分子量: 848.763
• InChiKey: XRTRCOOXTHHARE-PWGRSMRYSA-N

物化性质

• 熔点：
  80-82 °C
• 沸点：
  791.2±60.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  59
• 可旋转键数：
  25
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  283
• 氢给体数：
  0
• 氢受体数：
  23

反应信息

• 作为反应物：
  描述：

  2',2'',3,3',3'',4'',6,6',6''-nona-O-acetyl-D-maltotrial 在 sodium tetrahydroborate 、 mercury(II) diacetate 作用下， 生成 Glc2Ac3Ac4Ac6Ac(a1-4)Glc2Ac3Ac6Ac(a1-4)2-deoxy-D-araHex3Ac6Ac
  参考文献：
  名称：

  Mercuration-reductive demercuration of glycals: A mild and convenient entry to 2-deoxy-sugars

  摘要：

  Protected glycals, derived from mono-, di-and tri-saccharides, were easily and efficiently converted into the corresponding 2-deoxy-sugars, by reaction with mercuric(II) acetate/sodium borohydride in a polar solvent at 0 degrees C. The mild and non acidic reaction conditions permit the survival of acid-labile groups, such as silyl ethers. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00281-6
• 作为产物：
  描述：

  2,2’,2’’,3,3’,3’’,4’’,6,6’,6’’-deca-O-acetylmaltotriosyl bromide 在 sodium acetate 、 copper(II) sulfate 、 锌 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 2.5h， 以1.1 g的产率得到2',2'',3,3',3'',4'',6,6',6''-nona-O-acetyl-D-maltotrial
  参考文献：
  名称：

  乙酸钯 (II) 催化氰化三甲基甲硅烷基氰化物对过氧乙酰基乙二醇进行多糖和三糖氰化物的温和合成

  摘要：

  发现催化量 (1-2 mol%) 的乙酸钯 (II) 可用作二糖和三糖过氧乙酰乙二醇与氰化三甲基甲硅烷基氰化反应生成二糖和三糖 2-吡喃糖基的催化剂氰化物具有高产率和中等立体选择性。

  DOI：

  10.1055/s-2008-1032183

文献信息

• A versatile strategy for the synthesis of N-linked glycoamino acids from glycals
  作者：Vipin Kumar、Namakkal G. Ramesh

  DOI：10.1039/b712841j

  日期：——

  readily available glycals is reported. A variety of glycals possessing different carbohydrate templates (mono-, di- and trisaccharide glycals) were shown to undergo a novel iodine catalyzed stereoselective diamination reaction with chloramine-T. Taking advantage of the difference in the reactivity between the anomeric and C2 sulfonamido groups of these diamines 7, 13, 15, 17 and 19, they could be protected

  据报道，从容易获得的糖中合成N-连接的糖氨基酸的通用途径。具有不同碳水化合物模板的各种糖（单糖，二糖和三糖糖）已显示与氯胺-T发生新的碘催化的立体选择性渗氨基反应。利用这些二胺7、13、15、17和19的异头和C2磺酰胺基之间反应性的差异，可以在C2和异头氮原子上对其进行不同保护。因此，这些二胺的化学选择性乙酰化安装了C2乙酰氨基基团，这是一种必不可少的功能，在诱导N-连接的糖蛋白的β转角中起着至关重要的作用。随后保护20a，b的异头氮 e作为它们的Alloc（烯丙氧基羰基）衍生物，然后由SmI（2）介导的轻度二糖基化，得到24a-c。24a和24c的Alloc基团的脱保护以及释放的游离胺与多种受保护的氨基酸的偶联以高收率提供了N-连接的糖氨基酸25和27。还报道了N-连接的糖肽29的示例性合成。
• Ligand‐Controlled Stereoselective Synthesis of 2‐Deoxy‐β‐C‐glycosides by Cobalt Catalysis
  作者：Bingxue Liu、Deguang Liu、Xianle Rong、Xi Lu、Yao Fu、Qiang Liu

  DOI：10.1002/anie.202218544

  日期：——

  A ligand-controlled cobalt-catalyzed hydroalkylation of glycals was developed to access 2-deoxy-β-C-alkyl glycosides. This method exhibits broad substrate scope and excellent diastereoselectivity under very mild conditions. In addition, unprecedented stereodivergent synthesis of 2-deoxy-C-ribofuranosides was achieved using different chiral bisoxazoline ligands.

  开发了配体控制的钴催化的甘醇加氢烷基化反应以获得 2-脱氧-β-C-烷基糖苷。该方法在非常温和的条件下表现出广泛的底物范围和出色的非对映选择性。此外，使用不同的手性双恶唑啉配体实现了前所未有的 2-脱氧-C-呋喃核糖苷的立体发散合成。
• 一种烯糖化合物的合成方法
  申请人：江西科技师范大学

  公开号：CN114456217A

  公开（公告）日：2022-05-10

  一种烯糖化合物的合成方法是，以酰基保护、硅烷基或烷氧基保护的糖与三芳基或三烷基膦为原料，于室温条件下加入有机溶剂充分溶解，在20~60℃条件下反应2~36小时，得到磷盐中间化合物，然后在碱性条件下水解，反应结束后萃取，收集有机相，溶剂旋干后重新溶解于甲苯、乙醚或甲基叔丁基醚，过滤去除不溶物，旋干溶剂后经硅胶柱层析分离得到目标烯糖化合物。本发明实现以三取代膦为氧化剂的还原消除反应得到烯糖化合物，另外选择氘代氢氧化钠与氘代水为碱性条件时，可以得到相应的1‑D‑烯糖化合物，反应具有操作简便、原料廉价易得、反应收率高等特点，是一种具有较好应用前景的合成方法。
• Syntheses of 2-deoxy-2-fluoro mono- and oligo-saccharide glycosides from glycals and evaluation as glycosidase inhibitors
  作者：John D. McCarter、Michael J. Adam、Curtis Braun、Mark Namchuk、Dedreia Tull、Stephen G. Withers

  DOI：10.1016/0008-6215(93)84061-a

  日期：1993.10

  Several fluorinated oligosaccharides, including 2-deoxy-2-fluoro derivatives of cellobiose, maltose, and maltotriose were synthesized by the action of fluorine or acetyl hypofluorite on the corresponding glycal peracetates. Temperature effects on the stereoselectivities of these reactions were examined. Addition of acetyl hypofluorite to several 2-substituted glycals in the gluco or galacto series gave 2,2-disubstituted arabino- or lyxo-hexose derivatives; 3,4,6-tri-O-acetyl-2-fluoro-D-glucal or the analogous galactal yielded 2-deoxy-2,2-difluoro arabino- or lyxo-hexose peracetates, whereas 2-acetoxy-3,4,6-tri-O-acetyl-D-glucal or the analogous galactal gave 2(R)-2-acetoxy-2-fluoro-arabino- or lyxo-hexose peracetates, respectively. 2-Acetamido-3,4,6-tri-O-acetyl-D-glucal gave 2(R)-2-acetamido-2-acetoxy-3,4,6-tri-O-acetyl-alpha-D-arabino-hexopyranosyl fluoride. 2,4-Dinitrophenyl 2-deoxy-2-fluoro-beta-cellobioside was an inactivator of the exoglucanase from Cellulomonas fimi while 2-deoxy-2-fluoro-alpha-maltosyl and alpha-maltotriosyl fluorides were slow substrates of human pancreatic alpha-amylase and rabbit muscle glycogen debranching enzyme, respectively.