2,3,4,6-四-o-乙酰基-alpha-d-吡喃葡萄糖苷甲酯 | 604-70-6

• 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: 2,3,4,6-四-o-乙酰基-alpha-d-吡喃葡萄糖苷甲酯
• 英文名称: Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-methoxy-tetrahydro-pyran-4-yl ester
• 英文别名: methyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside；1-O-methyl-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside；alpha-D-Glucopyranoside methyl tetraacetate；[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-methoxyoxan-2-yl]methyl acetate
• CAS: 604-70-6
• 化学式: C₁₅H₂₂O₁₀
• mdl: MFCD00076081
• 分子量: 362.334
• InChiKey: UYWUMFGDPBMNCA-QMIVOQANSA-N

物化性质

• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.733
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  2,3,4,6-四-o-乙酰基-alpha-d-吡喃葡萄糖苷甲酯 在 氢氟酸 作用下， 反应 2.0h， 生成 2,3,4,6-四-O-乙酰基-α-D-吡喃葡萄糖酰氟
  参考文献：
  名称：

  A one-pot procedure for the quantitative conversion of glycosides into acetylated glycosyl fluorides

  摘要：

  DOI：

  10.1016/0008-6215(95)00328-2
• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-2-O-benzyl-α-D-galactopyranosyl bromide 在 methyl 2,3,4-tri-O-acetyl-6-O-trityl-α-D-glucopyranoside 、 18-冠醚-6 、 triphenylmethyl perchlorate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 生成 2,3,4,6-四-o-乙酰基-alpha-d-吡喃葡萄糖苷甲酯
  参考文献：
  名称：

  A new stereospecific method for 1,2-cis-glycosylation

  摘要：

  A new stereospecific method for 1,2-cis-glycosylation involves the reaction of 1,2-trans-glycosyl thiocyanates with sugar trityl ethers in the presence of triphenylmethylium perchlorate, The method has been applied to give disaccharide derivatives with (1 --> 6), (1 --> 4),(1 --> 3), and (1 --> 2) linkages.

  DOI：

  10.1016/0008-6215(91)84047-i
• 作为试剂：
  描述：

  (4aS,7aR)-1-Trimethylsilanyloxy-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester 在 三氟甲磺酸三甲基硅酯 、 2,3,4,6-四-o-乙酰基-alpha-d-吡喃葡萄糖苷甲酯 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以95%的产率得到methyl 1-[(4-methoxycarbonyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-1-yl)oxy]-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
  参考文献：
  名称：

  Tietze, Lutz F.; Fischer, Roland; Remberg, Gerd, Liebigs Annalen der Chemie, 1987, p. 971 - 976

  摘要：

  DOI：

文献信息

• Studies on the constituents of Momordica cochinchinensis Spreng. II. Isolation and characterization of the root saponins, Momordins I, II and III.
  作者：MASAYO IWAMOTO、HIKARU OKABE、TATSUO YAMAUCHI

  DOI：10.1248/cpb.33.1

  日期：——

  From the root of Momordica cochinchinensis SPRENG. (Cucurbitaceae), three saponins named momordins I, II and III have been isolated. Their structures were determined on the basis of chemical and spectral evidence as oleanolic acid 3-O-α-L-arabinopyranosyl (1→3)-β-D-glucuronopyranoside (momordin I), 28-O-β-D-glucopyranoside of momordin I (momordin II) and 3β-hydroxy-11α, 12α-epoxy-olean-28, 13-olide 3-O-α-L-arabinopyranosyl (1→3)-β-D-glucuronopyranoside (momordin III). Momordin II was proved to be identical with hemsloside Ma1 isolated from the tubers of Hemsleya macrosperma and H. chinensis.

  从木鳖子（Momordica cochinchinensis SPRENG. 葫芦科）的根中分离出三种皂苷，命名为木鳖子苷I、II和III。它们的结构通过化学和光谱证据确定为：木鳖子苷I（3-O-α-L-阿拉伯吡喃糖基（1→3）-β-D-葡萄糖醛酸苷基的齐墩果酸）、木鳖子苷II（木鳖子苷I的28-O-β-D-葡萄糖苷）和木鳖子苷III（3β-羟基-11α, 12α-环氧-齐墩果-28, 13-内酯的3-O-α-L-阿拉伯吡喃糖基（1→3）-β-D-葡萄糖醛酸苷）。木鳖子苷II被证实与从大苞赤瓟和中华赤瓟块根中分离出的hemsloside Ma1相同。
• Widely Useful DMAP-Catalyzed Esterification under Auxiliary Base- and Solvent-Free Conditions
  作者：Akira Sakakura、Kimio Kawajiri、Takuro Ohkubo、Yuji Kosugi、Kazuaki Ishihara

  DOI：10.1021/ja075824w

  日期：2007.11.28

  catalytic condensation of carboxylic acids with equimolar amounts of alcohols is the most desirable. Although several highly active dehydration catalysts have been reported, more efficient alternatives are still strongly needed because the dehydrative esterification of tertiary alcohols, phenols, acid-sensitive alcohols, amino acids, and hardly soluble alcohols has never proceeded satisfactorily. Here

  关于原子经济性和 E 因子，羧酸与等摩尔量的醇的催化缩合是最理想的。尽管已经报道了几种高活性脱水催化剂，但仍然强烈需要更有效的替代品，因为叔醇、酚、酸敏感醇、氨基酸和难溶性醇的脱水酯化从未令人满意地进行。在这里，我们报告了对经典 DMAP 催化醇酰化的新见解：令人惊讶的是，仅 0.05-2 mol% 的 DMAP 就可以在无碱和无溶剂的辅助条件下有效地促进醇与酸酐的酰化，从而得到相应的酯高产量。此外，我们在不使用任何溶剂的情况下实现了市售聚苯乙烯支持的 DMAP 的回收和再利用。这些偶然发现提供了广泛有用且环境友好的酯化方法，这可能比催化脱水缩合方法更实用和可靠，特别是对于几乎不与羧酸直接缩合的反应性较低的醇。
• Glycosylation of α-amino acids by sugar acetate donors with InBr3. Minimally competent Lewis acids
  作者：Mark R. Lefever、Lajos Z. Szabò、Bobbi Anglin、Michael Ferracane、Joanna Hogan、Lauren Cooney、Robin Polt

  DOI：10.1016/j.carres.2012.01.008

  日期：2012.4

  glycoside formation, but also promote undesired reactions of the glycoside products. Use of 'minimally competent' Lewis acids such as InBr(3) promotes the desired activation catalytically, and with greatly reduced side products from sugar peracetates.

  描述了一种用于制备用于 O 联糖肽合成的 Fmoc-丝氨酸和 Fmoc-苏氨酸糖苷的简化方法。路易斯酸促进糖苷形成，但也促进糖苷产物的不希望的反应。使用“最低限度的”路易斯酸（如 InBr(3)）可促进所需的活化催化，并大大减少过乙酸糖的副产物。
• Glycosidation catalust and process for preparing glycoside derivatives
  申请人：Nippon Fine Chemical Co., Ltd.

  公开号：US04874852A1

  公开（公告）日：1989-10-17

  Disclosed are a glycosidation catalyst comprising at least one of heteropoly acids represented by the formula H.sub.a X.sub.p M.sub.q O.sub.r .multidot.bH.sub.2 O wherein X is P, As, Si or Ge, M is at least one species selected from the group consisting of Mo, W and V, a is 3 4 or 6, b is an integer of 0 to 30, p is 1 or 2, q is 12 or 18, and r is 40 or 62, with the proviso that when X is P or As, a is 3 or 6; when X is Si or Ge, a is 4; and further (1) when X is P or As and a is 3, or when X is Si or Ge and a is 4, M is at least one species selected from the group consisting of Mo, W and V, p is 1, q is 12 and r is 40; and (2) when X is P or As and a is 6, M is Mo or W, p is 2, q is 18 and r is 62, and a process for preparing a glycoside derivative by using said catalyst.

  揭示了一种糖苷化催化剂，包括由公式H.sub.a X.sub.p M.sub.q O.sub.r .multidot.bH.sub.2 O表示的至少一种杂多酸，其中X为P、As、Si或Ge，M至少是来自Mo、W和V组成的群体中选择的一种物种，a为3、4或6，b为0至30的整数，p为1或2，q为12或18，r为40或62，但当X为P或As时，a为3或6；当X为Si或Ge时，a为4；进一步地（1）当X为P或As且a为3，或者当X为Si或Ge且a为4时，M为来自Mo、W和V组成的群体中选择的至少一种物种，p为1，q为12，r为40；以及（2）当X为P或As且a为6时，M为Mo或W，p为2，q为18，r为62，以及使用所述催化剂制备糖苷衍生物的方法。
• Samarium Trifluoromethanesulfonate: An Efficient Moisture Tolerant Acylation Catalyst under Solvent‐Free Condition
  作者：Bimalendu Roy、Somnath Dasgupta、Vishal Kumar Rajput、Balaram Mukhopadhyay

  DOI：10.1080/07328300801991245

  日期：2008.5

  Samarium trifluoromethanesulfonate catalyzed the acylation of phenols, alcohols, thiols, free reducing sugars, and glycosides in excellent yields at ambient temperature under solvent‐free condition using stoichiometric amounts of various anhydrides.

  在无溶剂条件下，使用化学计量的各种酸酐，三氟甲烷磺酸催化苯酚，醇，硫醇，游离还原糖和糖苷的酰化反应具有优异的收率。

表征谱图