2-C-(hydroxymethyl)-2,3:5,6-di-O-isopropylidene-α-D-mannofuranose | 91738-34-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-C-(hydroxymethyl)-2,3:5,6-di-O-isopropylidene-α-D-mannofuranose
• 英文别名: (3aS,4S,6R,6aS)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3a-(hydroxymethyl)-2,2-dimethyl-6,6a-dihydro-4H-furo[3,4-d][1,3]dioxol-4-ol
• CAS: 91738-34-0
• 化学式: C₁₃H₂₂O₇
• 分子量: 290.313
• InChiKey: SGJOYWAHFNJARE-NKGMTQDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  86.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-C-(hydroxymethyl)-2,3:5,6-di-O-isopropylidene-α-D-mannofuranose 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 palladium on activated charcoal 咪唑 、 盐酸 、 叔丁基过氧化氢 、 4-二甲氨基吡啶 、 sodium periodate 、 四丙基高钌酸铵 、 4-(2-dimethylaminophenyl)-pyridine 、 4 A molecular sieve 、 vanadyl acetylacetonate 、 potassium tert-butylate 、 四丁基氟化铵 、 氢气 、 仲丁基锂 、 sodium methylate 、 sodium hydride 、 碳酸氢钠 、 戴斯-马丁氧化剂 、 溶剂黄146 、 N-甲基吗啉氧化物 、 三乙胺 、 对甲苯磺酰氯 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 癸烷 、 正己烷 、 二氯甲烷 、 环己烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 、 苯 为溶剂， 反应 230.55h， 生成 卵假散囊菌素
  参考文献：
  名称：

  从d-甘露糖开始合成卵磷脂

  摘要：

  描述了环氧酮22的新合成方法，它是Barton合成卵磷脂（2）（一种强大的抗血管生成抑制剂）的关键中间体。构造22的关键过程是从2,3：5,6-二-O-异亚丙基-α - d-甘露呋喃糖（4）获得的烯烃11和12的闭环复分解和tri-TES醚的区域选择性脱甲硅烷基化19。此外，从一个替代立体选择性路线22到2也已开发，和的总产率2从4为10.0％。

  DOI：

  10.1021/jo051686m
• 作为产物：
  描述：

  2-C-hydroxymethyl-2,3:5,6-di-O-isopropylidene-D-mannono-1,4-lactone 在 二异丁基氢化铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 2.0h， 生成 2,3:5,6-di-O-isopropylidene 2-C-hydroxymethyl-β-D-mannofuranose 、 2-C-(hydroxymethyl)-2,3:5,6-di-O-isopropylidene-α-D-mannofuranose
  参考文献：
  名称：

  Synthesis of 2-C-branched derivatives of d-mannose: 2-C-aminomethyl-d-mannose binds to the human C-type lectin DC-SIGN with affinity greater than an order of magnitude compared to that of d-mannose

  摘要：

  2-C-Substituted branched D-mannose analogues are novel monosaccharides, readily obtained from a Kiliani-acetonation sequence on D-fructose, followed by subsequent functional group manipulation. 2-C-Azidomethyl-D-mannose and 2-C-aminomethylD-marmose bind to the C-type lectin DC-SIGN (CD209) with significantly greater affinity than mannose. In particular, 2-C-aminomethyl-D-mannose exhibits a comparative 48-fold increase in binding as determined using a surface plasmon resonance-based competition assay. DC-SIGN is an important cell-surface type II transmembrane protein that interacts with blood group antigens, endogenous glycoproteins such as ICAM-3, and also deadly pathogens such as the human immunodeficiency and hepatitis C viruses. The effective use of small compounds to block target binding by mannose-selective C-type lectins at sub-millimolar concentrations has not been shown previously; thus, these data represent a very attractive thoroughfare to novel antiviral and immunomodulatory drug development. @ 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.06.003

文献信息

• Synthesis of 3-C-(hydroxymethyl)erythritol and 3-C-methylerythritol
  作者：Zbigniew J. Witczak、Roy L. Whistler、James R. Daniel

  DOI：10.1016/0008-6215(84)85201-5

  日期：1984.10

  3-C-(Hydroxymethyl)erythritol was prepared from 3-C-(hydroxymethyl)-2,3-O-isopropylidene-D-erythro-tetrofuranose (4) by hydrolysis followed by reduction, or by reduction followed by hydrolysis. Monotosylation of 4, followed by reduction with lithium aluminum hydride and hydrolysis, afforded 3-C-methylerythritol.

  由3-C-（羟甲基）-2,3-O-异亚丙基-D-赤型-四呋喃糖（4）通过水解然后还原，或通过还原然后水解来制备3-C-（羟甲基）赤藓糖醇。4的单甲苯磺酰化，然后用氢化铝锂还原并水解，得到3-C-甲基赤藓糖醇。
• Synthesis of differentially protected cyclopentitol: its application towards the stereoselective synthesis of 5-epi-calditol
  作者：C.V. Ramana、Bethi Sridhar Reddy、Mukund K. Gurjar

  DOI：10.1016/j.tetlet.2004.02.020

  日期：2004.3

  The synthesis of differentially protected cyclopentitol derivative 5 is described using ring-closing metathesis of a diene derived froni D-mannose. Subsequent chemical 11 modifications such as catalytic osmylation and chain extension using glycidyl triflate completed the synthesis of 5-epi-calditol. (C) 2004 Elsevier Ltd. All rights reserved.
• Branched-chain alditols. A convenient synthesis of 6-deoxy-2-O-methyl-D-mannitol and 2-C-(hydroxymethyl)-D-mannitol
  作者：Zbigniew J. Witczak、Roy L. Whistler

  DOI：10.1016/0008-6215(87)80257-4

  日期：1987.11
• Synthesis of 2-C-branched derivatives of d-mannose: 2-C-aminomethyl-d-mannose binds to the human C-type lectin DC-SIGN with affinity greater than an order of magnitude compared to that of d-mannose
  作者：Daniel A. Mitchell、Nigel A. Jones、Stuart J. Hunter、Joseph M.D. Cook、Sarah F. Jenkinson、Mark R. Wormald、Raymond A. Dwek、George W.J. Fleet

  DOI：10.1016/j.tetasy.2007.06.003

  日期：2007.7

  2-C-Substituted branched D-mannose analogues are novel monosaccharides, readily obtained from a Kiliani-acetonation sequence on D-fructose, followed by subsequent functional group manipulation. 2-C-Azidomethyl-D-mannose and 2-C-aminomethylD-marmose bind to the C-type lectin DC-SIGN (CD209) with significantly greater affinity than mannose. In particular, 2-C-aminomethyl-D-mannose exhibits a comparative 48-fold increase in binding as determined using a surface plasmon resonance-based competition assay. DC-SIGN is an important cell-surface type II transmembrane protein that interacts with blood group antigens, endogenous glycoproteins such as ICAM-3, and also deadly pathogens such as the human immunodeficiency and hepatitis C viruses. The effective use of small compounds to block target binding by mannose-selective C-type lectins at sub-millimolar concentrations has not been shown previously; thus, these data represent a very attractive thoroughfare to novel antiviral and immunomodulatory drug development. @ 2007 Elsevier Ltd. All rights reserved.
• Synthesis of Ovalicin Starting from <scp>d</scp>-Mannose
  作者：Shunya Takahashi、Nobuyuki Hishinuma、Hiroyuki Koshino、Tadashi Nakata

  DOI：10.1021/jo051686m

  日期：2005.11.1

  A new synthesis of epoxyketone 22 is described that is a key intermediate in Barton's synthesis of ovalicin (2), a powerful anti-angiogenetic inhibitor. The key process for the construction of 22 was ring-closing metathesis of olefins 11 and 12 obtained from 2,3:5,6-di-O-isopropylidene-α-d-mannofuranose (4) and regioselective desilylation of tri-TES ether 19. Furthermore, an alternative stereoselective

  描述了环氧酮22的新合成方法，它是Barton合成卵磷脂（2）（一种强大的抗血管生成抑制剂）的关键中间体。构造22的关键过程是从2,3：5,6-二-O-异亚丙基-α - d-甘露呋喃糖（4）获得的烯烃11和12的闭环复分解和tri-TES醚的区域选择性脱甲硅烷基化19。此外，从一个替代立体选择性路线22到2也已开发，和的总产率2从4为10.0％。