3,5,6-tri-O-benzyl-4a-carba-β-D-galactofuranose | 1005004-09-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,5,6-tri-O-benzyl-4a-carba-β-D-galactofuranose
• 英文别名: (1R,2S,3S,4S)-4-[(1S)-1,2-bis(phenylmethoxy)ethyl]-3-phenylmethoxycyclopentane-1,2-diol
• CAS: 1005004-09-0
• 化学式: C₂₈H₃₂O₅
• 分子量: 448.559
• InChiKey: QXJRWVLAVPSMPU-WMJDNDCMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,5,6-tri-O-benzyl-4a-carba-β-D-galactofuranose 在 偶氮二甲酸二异丙酯 、 三氟化硼乙醚 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 (1S,2S,3S,5R)-2-(benzyloxy)-5-(((1S,2S,3S,5R)-2-(benzyloxy)-3-((S)-1,2-bis(benzyloxy)ethyl)-5-(((3aR,4R,6S,7S,7aR)-4-methoxy-2,2,6-trimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-7-yl)oxy)cyclopentyl)oxy)-3-((S)-1,2-bis(benzyloxy)ethyl)cyclopentan-1-ol
  参考文献：
  名称：

  Carbasugar analogues of galactofuranosides: β-O-linked derivatives and towards β-S-linked derivatives

  摘要：

  A selectively protected carbasugar analogue of beta-galactofuranose was synthesised from glucose using ring-closing metathesis as the key step. The carbasugar was converted into an alpha-galacto configured 1,2-epoxide, which was an effective electrophile in Lewis acid catalysed coupling reactions with alcohols. The epoxide was opened with regioselective attack at C-1 to give beta-galacto configured C-1 ethers. Using carbohydrates as nucleophiles, we synthesised a number of pseudodisaccharides. The epoxide was also regioselectively opened at C-1 with a sulfur nucleophile under basic conditions to give a beta-galacto configured C-1 thioether. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.04.032
• 作为产物：
  描述：

  3,4,6-三-O-苄基葡萄糖 在 盐酸 、 正丁基锂 、 Hoveyda-Grubbs catalyst second generation 、 草酰氯 、 palladium 10% on activated carbon 、 氢气 、 4-甲基苯磺酸吡啶 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 溶剂黄146 、 乙酸乙酯 、 甲苯 为溶剂， 反应 6.25h， 生成 3,5,6-tri-O-benzyl-4a-carba-β-D-galactofuranose
  参考文献：
  名称：

  Carbasugar analogues of galactofuranosides: β-O-linked derivatives and towards β-S-linked derivatives

  摘要：

  A selectively protected carbasugar analogue of beta-galactofuranose was synthesised from glucose using ring-closing metathesis as the key step. The carbasugar was converted into an alpha-galacto configured 1,2-epoxide, which was an effective electrophile in Lewis acid catalysed coupling reactions with alcohols. The epoxide was opened with regioselective attack at C-1 to give beta-galacto configured C-1 ethers. Using carbohydrates as nucleophiles, we synthesised a number of pseudodisaccharides. The epoxide was also regioselectively opened at C-1 with a sulfur nucleophile under basic conditions to give a beta-galacto configured C-1 thioether. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.04.032

文献信息

• First synthesis of 4a-carba-β-d-galactofuranose
  作者：Jens Frigell、Ian Cumpstey

  DOI：10.1016/j.tetlet.2007.10.138

  日期：2007.12

  The synthesis of 4a-carba-β-d-galactofuranose is described starting from diacetone glucose. The key ring-closure step was carried out by metathesis to form a cyclopentene. Catalytic hydrogenation of the CC double bond gave the galacto configured saturated carbahexofuranose with excellent diastereoselectivity.

  描述了从双丙酮葡萄糖开始的4a-氨基甲酸酯-β-d-半乳糖呋喃糖的合成。通过复分解进行关键环闭合步骤以形成环戊烯。CC双键的催化加氢得到具有出色的非对映选择性的半乳糖构型的饱和呋喃呋喃呋喃糖。
• Carbasugar Analogues of Galactofuranosides: Pseudodisaccharide Mimics of Fragments of Mycobacterial Arabino­galactan
  作者：Jens Frigell、Jean A. Pearcey、Todd L. Lowary、Ian Cumpstey

  DOI：10.1002/ejoc.201001380

  日期：2011.3

  A partially protected carbasugar analogue of β-galactofuranose was converted into an α-galacto configured 1,2-epoxide, which was was opened by alcohols under Lewis acid catalysis with regioselectiv ...

  部分保护的 β-呋喃半乳糖类似物被转化为 α-半乳糖配置的 1,2-环氧化物，在路易斯酸催化下通过区域选择性的醇将其打开。
• Carbasugar analogues of galactofuranosides: α-<i>O</i>-linked derivatives
  作者：Jens Frigell、Ian Cumpstey

  DOI：10.3762/bjoc.6.129

  日期：——

  Using an indirect method, we have synthesised α-linked carbasugar analogues of galactofuranosides for the first time. Ring opening of a β-talo configured carbasugar 1,2-epoxide by alcohol nucleophiles under Lewis acidic conditions proceeded with very good regioselectivity to give α-talo configured C1-substituted ethers with a free OH-group at the C2 position. Inversion of configuration at C2 by an oxidation–reduction sequence gave the α-galacto configured carbahexofuranose C1 ethers. A carbadisaccharide corresponding to the Galf(α1→3)Manp substructure from Apodus deciduus galactomannan was synthesised to exemplify the method.

  我们首次使用间接方法合成了α-连接的卡巴糖类似物，用于半乳糖苷。在Lewis酸性条件下，通过醇亲核试剂开环β-talo配置的卡巴糖1,2-环氧化物，以非常好的区域选择性反应，得到α-talo配置的C1取代醚，C2位置具有自由的OH基团。通过氧化还原序列，在C2处进行构型反转，得到α-galacto配置的卡巴己糖醚。为了说明该方法，我们合成了来自Apodus deciduus半乳糖甘露聚糖的Galf(α1→3)Manp亚结构对应的卡巴二糖。
• Synthesis of carbadisaccharide mimics of galactofuranosides
  作者：Jens Frigell、Ian Cumpstey

  DOI：10.1016/j.tetlet.2009.06.115

  日期：2009.9

  A partially protected carbagalactofuranose was converted into a 1,2-anhydro derivative. This epoxide was opened with alcohol nucleophiles under Lewis acid catalysis to give beta-carbagalactofuranose pseudodisaccharides with excellent regioselectivity. (C) 2009 Elsevier Ltd. All rights reserved.