methyl 3-deoxy-4,5:7,8-di-O-isopropylidene-α,β-D-manno-2-octulopyranosonate | 114884-19-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-deoxy-4,5:7,8-di-O-isopropylidene-α,β-D-manno-2-octulopyranosonate
• 英文别名: 4,5,7,8-di-O-isopropylidene-3-deoxy-2-hydroxyl-D-mannooctopyranos-2-ulosonate；Methyl 4,5:7,8-Di-O-isopropylidene-3-deoxy-α-D-manno-2-octulosonate；Methyl 3-deoxy-4:5,7:8-di-O-isopropylidene-α-D-manno-octulosonate；methyl (3aR,4R,6R,7aR)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-hydroxy-2,2-dimethyl-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carboxylate
• CAS: 114884-19-4
• 化学式: C₁₅H₂₄O₈
• 分子量: 332.351
• InChiKey: BEGHRYNOKHMAEO-WPMOFKQCSA-N

物化性质

• 熔点：
  123 °C
• 沸点：
  402.0±45.0 °C(Predicted)
• 密度：
  1.239±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 3-deoxy-4,5:7,8-di-O-isopropylidene-α,β-D-manno-2-octulopyranosonate 在 sodium hydroxide 、 溶剂黄146 作用下， 反应 2.83h， 生成 3-deoxy-α-D-manno-oct-2-ulosonic acid
  参考文献：
  名称：

  亚烷基卡宾在异头CH键处插入。3-脱氧-d-阿拉伯糖-2-庚基磺酸（DAH）和3-脱氧-d-甘露糖-2-辛基磺酸（KDO）的合成

  摘要：

  提出了一种基于亚烷基卡宾的[1,5]-CH键插入作用使糖类与相应的3-deoxy-2-ulosonic酸同源的新方法。该方法的应用通过3-脱氧-d-阿拉伯糖-2-庚酸（DAH）和3-脱氧-d-甘露糖-2-辛酸（KDO）的合成来说明。

  DOI：

  10.1016/s0040-4039(02)01078-x
• 作为产物：
  描述：

  methyl 2,6-anhydro-3-deoxy-4,5:7,8-di-O-isopropylidene-D-glycero-D-galacto-octonate 生成 methyl 3-deoxy-4,5:7,8-di-O-isopropylidene-α,β-D-manno-2-octulopyranosonate
  参考文献：
  名称：

  合成KDO的3-deoxy-D-manno-2-octulosonic酸（KDO），2-deoxy-KDO和硫代糖苷的新策略

  摘要：

  为了在合成KDO的过程中利用合成中间体的优势，我们开发了一种新的策略，该策略基于含水杂Diels-Alder反应与衍生自D-甘油醛的水溶性二烯的反应，然后对新创建的双键进行二羟基化。研究了这些反应的立体选择性以产生2-脱氧-KDO，其通过烯醇盐被亚硫基化以产生β-硫代糖苷，其水解导致KDO。

  DOI：

  10.1016/s0040-4020(01)81292-8

文献信息

• Convenient Syntheses of 3-Deoxy-D-<i>manno</i>-2-octulosonic Acid (KDO) and 3-Deoxy-D-<i>glycero</i>-D-<i>galacto</i>-2-nonulosonic Acid (KDN) Derivatives from D-Mannose
  作者：Ken-ichi Sato、Tomoyuki Miyata、Ikuo Tanai、Yasuchika Yonezawa

  DOI：10.1246/cl.1994.129

  日期：1994.1

  6-di-O-isopropylidene-D-mannose and 2,3,4,5,6,7-hexa-O-benzyl-6-D-glycero-2,3,4,5-D-galacto-heptose with methyl 2-benzyloxycarbonylamino-2-(diethoxyphosphoryl)acetate gave the corresponding α-dehydroamino acid derivatives in good yields, respectively. They were converted to methyl 3-deoxy-4,5:7,8-di-O-isopropylidene-α-D-manno-2-octulopyranosonate and methyl (methyl 3-deoxy-D-glycero-β-D-galacto-2-nonulopyranosid)onate

  4-O-苄基-2,3:5,6-二-O-异亚丙基-D-甘露糖和2,3,4,5,6,7-六-O-苄基-6-D的Horner-Wittig反应-glycero-2,3,4,5-D-galacto-heptose 与 2-benzyloxycarbonylamino-2-(diethoxyphosphoryl) 乙酸甲酯分别以良好的产率得到相应的 α-脱氢氨基酸衍生物。它们被转化为甲基 3-deoxy-4,5:7,8-di-O-isopropylidene-α-D-manno-2-octulopyranosonate 和甲基 (methyl 3-deoxy-D-glycero-β-D-galacto- 2-nonulopyranosid)onate 通过 α-氧代链烷酸甲酯衍生物。
• Formal Synthesis of 3-Deoxy-d-manno-Octulosonic Acid (KDO) and 3-Deoxy-d-arabino-2-heptulosonic Acid (DAH)
  作者：Kwok Mong、Tapan Pradhan、Chun Lin

  DOI：10.1055/s-0032-1317932

  日期：——

  synthetic routes to 3-deoxy- d - manno -octulo­sonic acid (KDO) and 3-deoxy- d - arabino -2-heptulosonic acid (DAH) from common sugar substrates are reported. Chain homologation of the sugar substrates was accomplished by Wittig olefination and Corey–Fuchs alkynylation. A new cyclization strategy was investigated to access the desired pyranosyl isomer of the KDO target.

  报道了从常见糖底物合成 3-脱氧-d-甘露糖-辛糖酸 (KDO) 和 3-脱氧-d-阿拉伯糖-2-庚糖酸 (DAH) 的实用合成路线。糖底物的链同源化是通过 Wittig 烯化和 Corey-Fuchs 炔化完成的。研究了一种新的环化策略以获取所需的 KDO 目标吡喃糖基异构体。
• Frick, Wendelin; Kruelle, Thomas; Schmidt, Richard R., Liebigs Annalen der Chemie, 1991, # 5, p. 435 - 438
  作者：Frick, Wendelin、Kruelle, Thomas、Schmidt, Richard R.

  DOI：——

  日期：——
• 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.
• HORITO, SHIGEOMI;AMANO, MASAYO;HASHIMOTO, HIRONOBU, J. CARBOHYDR. CHEM., 8,(1989) N, C. 681-684
  作者：HORITO, SHIGEOMI、AMANO, MASAYO、HASHIMOTO, HIRONOBU

  DOI：——

  日期：——