(methoxycarbonyl)methyl α-D-glucopyranoside | 314238-21-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (methoxycarbonyl)methyl α-D-glucopyranoside
• 英文别名: methyl 2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyacetate
• CAS: 314238-21-6
• 化学式: C₉H₁₆O₈
• 分子量: 252.221
• InChiKey: VCDGVBMVFQWFFN-GXHGQEQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (methoxycarbonyl)methyl α-D-glucopyranoside 以 吡啶 为溶剂， 生成 methyl 2-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyacetate
  参考文献：
  名称：

  Hydrogen peroxide oxidation of palatinose and trehalulose: direct preparation of carboxymethyl α-d-glucopyranoside

  摘要：

  The direct oxidation of palatinose and trehalulose by hydrogen peroxide in acidic medium provided carboxymethyl alpha -D-glucopyranoside (alpha -CMG) in moderate to fair yields in a single step. The effect of catalytic sodium tungstate on the reaction was studied. alpha -CMG is a versatile synthon able to supply a glucosyl moiety through the acylation of alcohols or amines, via the opening of the delta -lactone obtained by acetylation. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01440-4
• 作为产物：
  描述：

  Isomaltulose 在 sodium tungstate 磷酸 、 双氧水 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 (methoxycarbonyl)methyl α-D-glucopyranoside
  参考文献：
  名称：

  Hydrogen peroxide oxidation of palatinose and trehalulose: direct preparation of carboxymethyl α-d-glucopyranoside

  摘要：

  The direct oxidation of palatinose and trehalulose by hydrogen peroxide in acidic medium provided carboxymethyl alpha -D-glucopyranoside (alpha -CMG) in moderate to fair yields in a single step. The effect of catalytic sodium tungstate on the reaction was studied. alpha -CMG is a versatile synthon able to supply a glucosyl moiety through the acylation of alcohols or amines, via the opening of the delta -lactone obtained by acetylation. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01440-4

文献信息

• Straightforward Route for Anchoring a Glucosyl Moiety onto Nucleophilic Species:  Reaction of Amines and Alcohols with Carboxymethyl 3,4,6-Tri-<i>O</i>-acetyl-α-<scp>d</scp>-glucopyranoside 2-<i>O</i>-Lactone
  作者：Stéphane Trombotto、Mathieu Danel、Juliette Fitremann、Alain Bouchu、Yves Queneau

  DOI：10.1021/jo0300237

  日期：2003.8.1

  The base-catalyzed reaction of carboxymethyl 3,4,6-tri-O-acetyl-alpha-D-glucopyranoside 2-O-lactone (prepared from isomaltulose) with amino acids and fatty amines under basic catalysis gave a series of new pseudoglucopeptides, nonionic amphiphiles, and polymerizable derivatives. The same reaction applied to alcohols provided the corresponding 2-(alpha-D-glucopyranosyloxy)acetyl esters with either basic

  在碱性催化下，羧甲基3,4,6-三-O-乙酰基-α-D-吡喃葡萄糖苷2-O-内酯（由异麦芽酮糖制备）与氨基酸和脂肪胺的碱催化反应产生了一系列新的假葡萄糖肽，非离子两亲物和可聚合衍生物。应用于醇的相同反应提供了带有碱性或酸性催化剂的相应的2-（α-D-吡喃葡萄糖基氧基）乙酰基酯。
• SACCHAROPEPTIDES AND DERIVATIVES THEREOF
  申请人：GLYCOMED INCORPORATED

  公开号：EP0824538A1

  公开（公告）日：1998-02-25
• [EN] SACCHAROPEPTIDES AND DERIVATIVES THEREOF<br/>[FR] SACCHAROPEPTIDES ET DERIVES
  申请人：——

  公开号：WO1996035700A1

  公开（公告）日：1996-11-14

  [EN] The present invention describes glycomimetic saccharopeptides of formula (I): W-(X)n-Y-[(X)n-W-(X)n-Y]m-(X)n-W, wherein W is independently selected from the group consisting of a) saccharides; b) aryl, aralkyl; c) alkyl of 1 to 8 carbon atoms, optionally substituted; d) cyclic alkyl or 5-7 carbon atoms, heterocyclic alkyl. Y is independently selected from the group consisting of -NR<3>-C(O)- and -C(O)-NR<3>-; X is a difunctional or polyfunctional group selected from the group consisting of a) aryl, aralkyl; b) alkyl of 1-8 carbon atoms, optionally substituted with 1-3 substituents. R is -H, or lower alkyl, lower aryl, and lower aralkyl; R' is independently selected from the group consisting of -H, lower alkyl of 1-4 carbon atoms, aralkyl of 2 to 19 carbon atoms, and -C(O)R"; R" is lower alkyl of 1 to 4 carbon atoms; and R<3> is selected from the group consisting of -H, alkyl of 1-8 carbon atoms, and aralkyl of 5-8 carbon atoms; and pharmaceutically acceptable salts thereof.
  [FR] La présente invention concerne des saccharopeptides glycomimétiques représentés par la formule générale (I): W-(X)n-Y-[(X)n-W-(X)n-Y]m-(X)n-W ainsi que certains de ses sels pharmacologiquement admis. Dans cette formule, W est choisi indépendamment dans le groupe constitué a) des saccharides, b) des aryles et aralkyles, c) des alkyles portant 1 à 8 atomes de carbone, éventuellement substitués et d) des alkyles cycliques ou des alkyles hétérocycliques portant 5 à 7 atomes de carbones. Y est choisi indépendamment dans le groupe constitué des -NR<3>-C(O) et -C(O)-NR<3>-. X est un groupe bifonctionnel ou polyfonctionnel choisi dans le groupe constitué a) des aryles et aralkyles et b) des alkyles portant 1 à 8 atomes de carbone ayant éventuellement 1 à 3 substituants. R est -H ou alkyle inférieur, aryle inférieur et aralkyle inférieur. R' est choisi indépendamment dans le groupe constitué des -H, alkyles inférieurs portant 1 à 4 atomes de carbone, aralkyles portant de 2 à 19 atomes de carbone et de -C(O)R". R" est alkyle inférieur portant 1 à 4 atomes de carbone. Enfin, R<3> est choisi dans le groupe constitué des -H, alkyles portant 1 à 8 atomes de carbone et aralkyles portant 5 à 8 atomes de carbone.