methyl O-(methyl 3-deoxy-4,5:7,8-di-O-isopropylidene-α-D-manno-2-octulopyranosonate)-(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside | 131444-89-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl O-(methyl 3-deoxy-4,5:7,8-di-O-isopropylidene-α-D-manno-2-octulopyranosonate)-(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
• 英文别名: methyl (methyl 3-deoxy-4,5:7,8-di-O-isopropylidene-α-D-manno-octulosonate)-(2->6)-(2,3,4-tri-O-benzyl-α-D-glucopyranoside)；methyl (3aR,4R,6R,7aR)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-[[(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methoxy]-2,2-dimethyl-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carboxylate
• CAS: 131444-89-8
• 化学式: C₄₃H₅₄O₁₃
• 分子量: 778.894
• InChiKey: QQDMSCMCYHYYQY-OOLZGBGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.46
• 重原子数：
  56.0
• 可旋转键数：
  15.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  127.83
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  methyl O-(methyl 3-deoxy-4,5:7,8-di-O-isopropylidene-α-D-manno-2-octulopyranosonate)-(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 在 palladium on activated charcoal sodium hydroxide 、 水 、 氢气 、 三氟乙酸 作用下， 以 甲醇 、 水 为溶剂， 反应 48.0h， 生成 Sodium; (2R,4R,5R,6R)-6-((R)-1,2-dihydroxy-ethyl)-4,5-dihydroxy-2-((2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylate
  参考文献：
  名称：

  含双糖的3-脱氧-d-甘露糖-2-辛磺酸的立体控制方法

  摘要：

  详细介绍了基于烯醇醚的立体控制碘环化合成含KDO的二糖合成方法的过程。

  DOI：

  10.1016/s0040-4039(00)97952-8
• 作为产物：
  描述：

  2-deoxy-3,4:6,7-di-O-isopropylidene-5-O-<<(trimethylsilyl)ethoxy>methyl>-D-manno-heptonic acid 在 吡啶 、 4-二甲氨基吡啶 、 sodium chlorite 、 草酰氯 、 potassium tert-butylate 、 四丁基氟化铵 、 双氧水 、 碘 、 sodium methylate 、 乙二胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 六甲基磷酰三胺 、 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 52.17h， 生成 methyl O-(methyl 3-deoxy-4,5:7,8-di-O-isopropylidene-α-D-manno-2-octulopyranosonate)-(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Cyclization of hydroxy enol ethers: a stereocontrolled approach to 3-deoxy-D-manno-2-octulosonic acid containing disaccharides

  摘要：

  A method for the preparation of the carboxylic acids 14 and 15 has been developed, starting from known 2,3,5,6-di-O-isopropylidene-D-mannofuranose. Esterification of 14 and 15 with methanol, methyl 2,3,4-tri-O-benzyl-alpha-D-glucopyranoside, and 1,2,5,6-di-O-isopropylidene-alpha-D-glucofuranose, followed by reaction with Tebbe reagent and selective deprotection gave, respectively, the key complex hydroxy enol ethers 20, 26, and 35. Stereoselective iodocyclization, followed by transformation of the CH2I appendage into a methyloxycarbonyl group, gave the corresponding protected KDO-containing disaccharides.

  DOI：

  10.1021/jo00041a017

文献信息

• Synthesis of 3-deoxy-d-manno-2-octulosonic acid (Kdo) and d-glycero-d-talo-2-octulosonic acid (Ko) and their α-glycosides
  作者：Martin Reiner、Richard R. Schmidt

  DOI：10.1016/s0957-4166(99)00557-1

  日期：2000.1

  Reaction of 2,3:5,6-di-O-isopropylidene-D-mannofuranose 1 with C-2 lithio derivatives of glyoxylate mercaptal in the presence of MgBr2 afforded D-glycero-D-galacto-2-octulosonates 2 and 3, respectively. Their 3-O-deoxygenation led to Kdo. N-Iodosuccinimide treatment of 3 gave thioglycoside 11 directly, which was transformed into Ko derivative 12 via epimerisation of the 3-hydroxy group. 3-O-Benzoylation of 12 and then transformation into phosphite furnished 15, an efficient glycosyl donor. Reaction of 15 with 6-O-unprotected glucosamine derivative 22 as acceptor gave alpha-glycoside 23, which was successfully transformed either into Kdo-disaccharide 27 or into Ko-disaccharide 29. (C) 2000 Elsevier Science Ltd. All rights reserved.
• ARNAUD, HAUDRECHY;PIERRE, SINAY, TETRAHEDRON LETT., 31,(1990) N0, C. 5765-5768
  作者：ARNAUD, HAUDRECHY、PIERRE, SINAY

  DOI：——

  日期：——