2,3,2',3'-tetra-O-benzyl-α,α-trehalose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,2',3'-tetra-O-benzyl-α,α-trehalose
• 英文别名: (2R,3R,4S,5R,6R)-6-[(2R,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-3,4-bis(phenylmethoxy)oxan-2-yl]oxy-2-(hydroxymethyl)-4,5-bis(phenylmethoxy)oxan-3-ol
• 化学式: C₄₀H₄₆O₁₁
• 分子量: 702.799
• InChiKey: WXWNXVODAVEHEI-AELZGUPMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  51
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  146
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2,3,2',3'-tetra-O-benzyl-α,α-trehalose 在 吡啶 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 2,3,4,2',3',4'-hexa-O-benzyl-6,6'-di-O-p-tolylsulfonyl-α,α-trehalose
  参考文献：
  名称：

  镜腔冠索因子的合成

  摘要：

  摘要受保护的双庚二糖醛酸，（2,3,4-三-O-苄基-6-脱氧-α-d-葡萄糖-庚基吡喃葡萄糖醛酸）2,3,4-三-O-苄基-6-脱氧-通过链长的羰基铁方法合成α-d-葡萄糖-庚基吡喃二葡萄糖醛酸，起始于2,3,4,2'，3'，4'-六-O-苄基-6,6'-di-邻甲苯磺酰基-α，α-海藻糖。还通过酸催化的其二酰胺的甲醇水解制备了其二甲酯，该二酰胺先前是通过另一种途径获得的。二酸经（外消旋）（2 RS，3 SR）-和（2 RS，3 RS）-3-O-苄基胭脂基烯醇酯化二酸，通过将合成的3-O-苄基甲基C 32-胭脂烯酸酯还原而获得氢化铝锂，以高收率提供了相应的二酯。产物的氢解脱苄基化导致“镜”冠状帘线因子。

  DOI：

  10.1016/0008-6215(93)80100-s
• 作为产物：
  描述：

  海藻糖 在 sodium hydride 、 对甲苯磺酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 2,3,2',3'-tetra-O-benzyl-α,α-trehalose
  参考文献：
  名称：

  用于膜蛋白研究的十二烷基海藻糖苷去污剂的合成和性质

  摘要：

  糖基洗涤剂，主要来自麦芽糖或葡萄糖，在膜蛋白的提取、增溶、稳定和结晶中占主导地位。受海藻糖广泛用于保护生物大分子和脂质双层结构的启发，我们合成了新的海藻糖苷去污剂，用于膜蛋白研究的潜在应用。我们设计了四种十二烷基海藻糖苷的有效合成方法，每种十二烷基海藻糖苷的 12 碳烷基链连接到海藻糖的不同羟基，从而呈现结构多样但相关的洗涤剂家族。评估洗涤剂的物理特性，包括溶解度、疏水性、临界胶束浓度 (CMC) 和胶束大小，并与最流行的麦芽糖苷类似物 β- d 进行比较。-十二烷基麦芽糖苷 (DDM)，由于不同的分子几何形状和所得胶束中可能的极性基团相互作用而彼此不同。还在甲醇中获得了 2-十二烷基海藻糖苷 (2-DDTre) 的晶体，晶体堆积显示相邻海藻糖基团之间存在多个 H 键相互作用。测试了少数海藻糖苷去污剂对伤害感受素/孤啡肽 FQ 肽受体 (ORL1) 和 MsbA 的溶解和稳定作用，它们分别属于

  DOI：

  10.1021/la3020404

文献信息

• ?-D-Glycosyl-Substituted ?,?-D-Trehaloses with (1 ? 4)-Linkage: Syntheses and NMR Investigations
  作者：Hans Peter Wessel、Gerhard Englert、Peter Stangier

  DOI：10.1002/hlca.19910740403

  日期：1991.6.19

  Two symmetrical trehalose glycosyl ‘acceptors’ 4 and 6 were prepared and three of the unsymmetrical type, 8, 10, and 11. Glucosylation of symmetrical ‘acceptor’ 4 gave a higher yield of trisaccharide (44%) than protect ve-group manipulation, namely via selective debenzylidenation 2 9 or monoacetylation 2 5 which proceeded in moderate yields (33–34%). A comparison of catalysts in the cis-glucosylation

  两个对称的海藻糖的糖基“受体” 4和6中制备和三个非对称型的，8，10，和11。对称的“受体” 4的糖基化比保护ve-基团操纵（即通过选择性脱苄基2 9或单乙酰化2 5）获得的三糖收率更高（44％），中等收率（33-34％）。海藻糖“受体” 10与四-O-苄基-β-D-吡喃葡萄糖基氟13的顺式-葡萄糖基化反应中催化剂的比较异三氟甲磺酸酐（（Tf）2 O）作为新的反应性启动子，产生92％的三糖14，解封得到目标糖α-D-吡喃葡萄糖基-（1 4）-α，α-D-海藻糖。对大多数化合物的1 H-NMR光谱进行了广泛的分析。提倡使用ID TOCSY技术的时间效率，如果需要的话还可以通过ROESY实验进行补充。
• An improved synthesis of 6-O--mycoloyl- and 6-O-corynomycoloyl-α,α-trehalose with observations on the permethylation analysis of trehalose glycolipids
  作者：Avraham Liav、Mayer B. Goren

  DOI：10.1016/s0008-6215(00)90151-4

  日期：1986.11
• Yoshimoto, Kimihiro; Wakamiya, Takako; Nishikawa, Yoshihiro, Chemical and pharmaceutical bulletin, 1982, vol. 30, # 4, p. 1169 - 1174
  作者：Yoshimoto, Kimihiro、Wakamiya, Takako、Nishikawa, Yoshihiro

  DOI：——

  日期：——
• Convenient Divergent Synthesis of a Library of Trehalosamine Analogues
  作者：Yu Hui、Cheng-Wei Tom Chang

  DOI：10.1021/ol026095m

  日期：2002.6.1

  A library of seven trehalosamine analogues with various natural and non-natural binding motifs was synthesized through an expedient divergent synthetic approach, The final products were prepared in sufficient quantities and purities for different types of assay against various pathogens. Several stereo- and regioselective reactions on the trehalose scaffold were developed for rapid synthesis of all of the designed compounds.
• The Synthesis of Four Dideoxygenated Analogues of β-Maltosyl-(1→4)-Trehalose
  作者：Hans Peter Wessel、Rudolf Minder、Michel Trumtel

  DOI：10.1080/07328309808001900

  日期：1998.11

  Four derivatives of beta-maltosyl-(1 -->4)-trehalose were prepared, each with two deoxy functions in one of the constitutive disaccharide building blocks. 2,3-Di-O-acetyl-4,6-dideoxy-4,6-diiodo-alpha-D-galactopyranosyl-(1-->4) -1,2,3,6-tetra-O-acetyl-D-glucopyranose (3) was employed as a precursor for the 4'",6'" -dideoxygenated tetrasaccharide 9: coupling of 3 with 2,3,6-tri-O-benzyl-alpha-D-glucopyranosyl 2,3,6-tri-O-benzylidene-alpha-D-glucopyranoside (4) furnished the tetrasaccharide 5 which was deiodinated and deprotected to yield the target tetrasaccharide 9. Secondly, the dideoxygenated maltose derivative 3-deoxy-4,6-O-isopropylidene-2-O-pivaloyl-alpha-D-glucopyranosyl-(1-->4)-1,6- anhydro-3-deoxy-2-O-pivaloyl-beta-D-glucopyranose (10) was ring-opened to the anomeric acetate 11. A [2+2] block synthesis with 4 in TMS triflate mediated glycosylation gave a tetrasaccharide which was deprotected to the 3 ",3'"- dideoxygenated analogue of beta-maltosyl-(1 -->4)-trehalose. For the third tetrasaccharide, 2,3,2',3'-tetra-O-benzyl-alpha,alpha-trehalose was iodinated at the primary positions and deiodinated in the presence of palladium-on-carbon, then this acceptor was selectively glycosylated with hepta-O-acetyl-maltosyl bromide (20). Removal of protective groups furnished the maltosyl trehalose tetrasaccharide deoxygenated at positions C-6 and C-6'. To prepare a 3,3'-dideoxygenated trehalose, the free hydroxyl groups of 2-O-benzyl-4,6-O-(R)-benzylidene-alpha-D-glucopyranosyl 2-O-benzyl-4,6-O-(R)-benzylidene-alpha-D-glucopryanoside (25) were reduced by Barton-McCombie deoxygenation. One of the benzylidene groups was opened reductively with sodium cyanoborohydride. The resulting free hydroxyl group at the 4'-position was glycosylated in a Koenigs-Knorr reaction with 20 to yield the 3,3'-dideoxygenated tetrasaccharide 32, the fourth target oligosaccharide, after deprotection.