2,3,4-tri-O-(4-methoxybenzyl)-L-fucopyranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4-tri-O-(4-methoxybenzyl)-L-fucopyranose
• 英文别名: (3S,4R,5R,6S)-3,4,5-tris[(4-methoxyphenyl)methoxy]-6-methyloxan-2-ol
• 化学式: C₃₀H₃₆O₈
• 分子量: 524.611
• InChiKey: DWPHENFVXZNHQE-ZMSWTNECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  84.8
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-(4-methoxybenzyl)-L-fucopyranose 在 四氯化碳 、 三(二甲胺基)膦 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以73%的产率得到2,3,4-tri-O-(4-methoxybenzyl)-α-L-fucopyranosyl chloride
  参考文献：
  名称：

  Synthesis of ?-fucosyl glycosides and disaccharides using 4-methoxybenzyl (Mpm) protected fucosyl donors

  摘要：

  The 4-methoxybenzyl (Mpm) group removable by selective oxidation was applied as a non-neighbouring-group-active protection of fucose hydroxy functions in the stereoselective synthesis of alpha-fucosides of acceptors containing double bonds sensitive to hydrogenation. With this aim, the synthesis of the alpha-fucosyl chloride (4) carrying the acid-sensitive Mpm protection was elaborated.

  DOI：

  10.1002/prac.19923340706
• 作为产物：
  描述：

  (Z/E)-propenyl-2,3,4-tri-O-(4-methoxybenzyl)-α-L-fucopyranoside 在 4-甲基苯磺酸吡啶 作用下， 以 乙醇 、 水 为溶剂， 反应 16.0h， 以70%的产率得到2,3,4-tri-O-(4-methoxybenzyl)-L-fucopyranose
  参考文献：
  名称：

  Synthesis of ?-fucosyl glycosides and disaccharides using 4-methoxybenzyl (Mpm) protected fucosyl donors

  摘要：

  The 4-methoxybenzyl (Mpm) group removable by selective oxidation was applied as a non-neighbouring-group-active protection of fucose hydroxy functions in the stereoselective synthesis of alpha-fucosides of acceptors containing double bonds sensitive to hydrogenation. With this aim, the synthesis of the alpha-fucosyl chloride (4) carrying the acid-sensitive Mpm protection was elaborated.

  DOI：

  10.1002/prac.19923340706

文献信息

• [EN] SYNTHESIS OF NEW FUCOSE-CONTAINING CARBOHYDRATE DERIVATIVES<br/>[FR] SYNTHÈSE DE NOUVEAUX DÉRIVÉS GLUCIDIQUES CONTENANT DU FUCOSE
  申请人：GLYCOM AS

  公开号：WO2012127410A1

  公开（公告）日：2012-09-27

  A method for the synthesis of a compound of formula (1) or a salt thereof, wherein A is a carbohydrate linker which is a lactosyl moiety or which consists of a lactosyl moiety and at least one monosaccharide unit selected from the group consisting of: glucose, galactose, N-acetylglucosamine, fucose and N-acetyl neuraminic acid; and wherein R1 is one of the following anomeric protecting groups: a) -OR2, wherein R2 is a protecting group removable by catalytic hydrogenolysis; b) -SR3, wherein R3 is an optionally substituted alkyl, an optionally substituted aryl or an optionally substituted benzyl; c) -NH- C(R")=C(R')2, wherein each R' independently is one of the following electron withdrawing groups: -CN, -COOH, -COO-alkyl, -CO-alkyl, -CONH2, -CONH- alkyl or -CON(alkyl)2, or wherein the two R'-groups are linked together and form -CO-(CH2)2-4-CO- and thus form, together with the carbon atom to which they are attached, a 5-7 membered cycloalkan-1,3-dione, in which dione any of the methylene groups is optionally substituted with 1 or 2 alkyl groups, and R" is H or alkyl, in which a fucosyl donor of formula (2) wherein X is selected from the group consisting of: a guanosine diphosphatyl moiety, a lactose moiety, azide, fluoride, optionally substituted phenoxy-, optionally substituted pyridinyloxy-, optionally substituted 3-oxo-furanyloxy- of formula (A), optionally substituted 1,3,5-triazinyloxy- of formula (B), 4-methylumbelliferyloxy-group of formula (C), and a group of formula (D) wherein Ra is independently H or alkyl, or two vicinal Ra groups represent a =C(Rb)2 group, wherein Rb is independently H or alkyl, Rc is independently selected from the group consisting of alkoxy, amino, alkylamino and dialkylamino, Rd is selected from the group consisting of H, alkyl and -C(=O)Re, wherein Re is OH, alkoxy, amino, alkylamino, dialkylamino, hydrazino, alkylhydrazino, dialkylhydrazino or trialkylhydrazino, is reacted with an acceptor of formula H-A-R1 or a salt thereof, wherein A and R1 are as defined above, under the catalysis of an enzyme capable of transferring fucose. A compound of formula 1', its use in manufacture of human milk oligosaccharides, a method of manufacture of human milk oligosaccharides, and a fucosyl donor are also provided.

  一种合成式（1）化合物或其盐的方法，其中A是一种碳水化合物连接物，其为乳糖基或由乳糖基和至少一种单糖单元组成，所述单糖单元选自以下组中的一种：葡萄糖、半乳糖、N-乙酰葡萄糖胺、岩藻糖和N-乙酰神经酸；R1是以下异构保护基之一：a）-OR2，其中R2是可通过催化氢解去除的保护基；b）-SR3，其中R3是可选的取代基烷基、可选的取代基芳基或可选的取代基苄基；c）-NH-C(R")=C(R')2，其中每个R'独立地是以下电子提取基之一：-CN、-COOH、-COO-烷基、-CO-烷基、-CONH2、-CONH-烷基或-CO N（烷基）2，或其中两个R'基连接在一起形成-CO-（CH2）2-4-CO-，并与它们连接的碳原子一起形成5-7环脂肪环-1,3-二酮，在该二酮中，任何亚甲基基团均可选地被1或2个烷基取代，R"为H或烷基，在式（2）中提供了一种岩藻糖供体，其中X选自以下组中的一种：鸟苷二磷酸基团、乳糖基、叠氮化物、氟化物、可选取代的苯氧基、可选取代的吡啶氧基、可选取代的3-氧代呋喃氧基式（A）、可选取代的1,3,5-三嗪氧基式（B）、4-甲基芹菜素氧基式（C）和式（D）中的基团，其中Ra独立地为H或烷基，或两个相邻的Ra基团表示=C（Rb）2基团，其中Rb独立地为H或烷基，Rc独立地选自烷氧基、氨基、烷基氨基和双烷基氨基，Rd选自H、烷基和-C（=O）Re，其中Re为OH、烷氧基、氨基、烷基氨基、双烷基氨基、肼基、烷基肼基、双烷基肼基或三烷基肼基，与式H-A-R1或其盐反应，其中A和R1如上所述，在能够转移岩藻糖的酶的催化下。还提供了式1'的化合物及其在制造人乳寡糖中的应用、制造人乳寡糖的方法和一种岩藻糖供体。
• [EN] GLYCOSYLATED GALACTOSYL DISACCHARDDES, METHODS FOR THEIR PRODUCTION AND THEIR USE IN CONSUMABLE PRODUCTS<br/>[FR] DISACCHARIDES GALACTOSYLIQUES GLYCOLYSÉS, PROCÉDÉS DE PRÉPARATION ET LEUR UTILISATION DANS DES PRODUITS CONSOMMABLES
  申请人：GLYCOM AS

  公开号：WO2013190529A1

  公开（公告）日：2013-12-27

  A method for modifying galactosyl disaccharides in order to enhance their bifidogenic effect, comprising reacting at least one glycosyl donor with a precursor galactosyl disaccharide or a mixture of precursor galactosyl disaccharides using enzyme catalysis, compounds obtainable by said method and the use of such compounds in consumable products.

  一种用于改性半乳糖二糖以增强其双歧杆菌效果的方法，包括使用酶催化作用，将至少一种糖基供体与前体半乳糖二糖或前体半乳糖二糖混合物反应，所得化合物及其在可食用产品中的使用。
• MODIFIED GALACTOOLIGOSACCHARIDES
  申请人：GLYCOM A/S

  公开号：US20150183816A1

  公开（公告）日：2015-07-02

  The invention relates to a method for making modified galactooligosaccharides comprising the step of enzymatic glycosylation, the modified galactooligosaccharides obtainable by the method and consumable products containing them.

  本发明涉及一种制备改性半乳寡糖的方法，包括酶促糖基化步骤，所述方法获得的改性半乳寡糖以及包含它们的可食用产品。
• METHOD FOR GENERATING HUMAN MILK OLIGOSACCHARIDES (HMOs) OR PRECURSORS THEREOF
  申请人：Dekany Gyula

  公开号：US20140234912A1

  公开（公告）日：2014-08-21

  A method for generating human milk oligosaccharides (HMOs) or precursors thereof, compounds obtainable by the method, and uses and compositions involving such compounds. The method comprising the steps of a) providing at least one donor selected from the group of compounds of any of formulae 5 to 10, b) providing at least one acceptor from a group of lactose, LNT, LNnT and derivatives thereof, c) providing at least one enzyme comprising a transglycosidase activity and/or a glycosynthase activity, d) preparing a mixture of the at least one donor, at least one acceptor and at least one enzyme provided in steps a), b) and c); and e) incubating the mixture prepared according to step d).

  一种生成人乳寡糖（HMO）或其前体的方法，该方法包括以下步骤：a）提供至少一种来自公式5至10中的化合物组的供体；b）提供至少一种来自乳糖、LNT、LNnT及其衍生物组的受体；c）提供至少一种具有转床苷酶活性和/或糖合成酶活性的酶；d）制备在步骤a）、b）和c）中提供的至少一种供体、至少一种受体和至少一种酶的混合物；e）孵育根据步骤d）制备的混合物。该方法所得到的化合物，以及使用该化合物的组合物和用途也包括在内。
• Method for generating human milk oligosaccharides (HMOs) or precursors thereof
  申请人：Dekany Gyula

  公开号：US09234225B2

  公开（公告）日：2016-01-12

  A method for generating human milk oligosaccharides (HMOs) or precursors thereof, compounds obtainable by the method, and uses and compositions involving such compounds. The method comprising the steps of a) providing at least one donor selected from the group of compounds of any of formulae 5 to 10, b) providing at least one acceptor from a group of lactose, LNT, LNnT and derivatives thereof, c) providing at least one enzyme comprising a transglycosidase activity and/or a glycosynthase activity, d) preparing a mixture of the at least one donor, at least one acceptor and at least one enzyme provided in steps a), b) and c); and e) incubating the mixture prepared according to step d).

  一种生成人类乳寡糖（HMOs）或其前体化合物的方法，以及由该方法获得的化合物、涉及此类化合物的用途和组合物。该方法包括以下步骤：a）提供至少一种来自任何5至10式化合物组的供体；b）提供来自乳糖、LNT、LNnT和其衍生物组的至少一种受体；c）提供至少一种具有转移酶活性和/或糖合成酶活性的酶；d）制备至少一种供体、至少一种受体和至少一种在步骤a）、b）和c）中提供的酶的混合物；以及e）孵育根据步骤d）制备的混合物。