(1R)-1-[(3aS,4S,6R,6aS)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]-2-(1,3-dithian-2-yl)ethanol | 127218-26-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R)-1-[(3aS,4S,6R,6aS)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]-2-(1,3-dithian-2-yl)ethanol
• CAS: 127218-26-2
• 化学式: C₁₄H₂₄O₅S₂
• 分子量: 336.474
• InChiKey: KBGOWJSIIQZOAQ-WSLQDRLSSA-N

物化性质

• 沸点：
  468.7±45.0 °C(predicted)
• 密度：
  1.30±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1R)-1-[(3aS,4S,6R,6aS)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]-2-(1,3-dithian-2-yl)ethanol 生成 6-deoxy-D-manno-heptose
  参考文献：
  名称：

  An efficient route to 3-deoxy-d-manno-2-octulosonic acid (KDO) derivatives via a 1,4-cyclic sulfate approach

  摘要：

  DOI：

  10.1016/s0040-4039(01)80598-0
• 作为产物：
  描述：

  methyl 2,3-O-isopropylidene-α-D-mannofuranoside 在 ruthenium trichloride 、 sodium periodate 、 氯化亚砜 、 硫酸 作用下， 生成 (1R)-1-[(3aS,4S,6R,6aS)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]-2-(1,3-dithian-2-yl)ethanol
  参考文献：
  名称：

  An efficient route to 3-deoxy-d-manno-2-octulosonic acid (KDO) derivatives via a 1,4-cyclic sulfate approach

  摘要：

  DOI：

  10.1016/s0040-4039(01)80598-0

文献信息

• A new 6-C-alkylation from an alkyl mannofuranoside 5,6-cyclic sulfate
  作者：Thierry Gourlain、Anne Wadouachi、Daniel Beaupère

  DOI：10.1016/s0008-6215(99)00275-x

  日期：2000.1

  Methyl 6-C-alkyl-6-deoxy-alpha-D-mannofuranoside derivatives have been synthesized from methyl 2,3-O-isopropylidene-5,6-O-sulfuryl-alpha-D-mannofuranoside (1). In a Path A, reaction of the 5,6-cyclic sulfate 1 with 2-lithio-1,3-dithiane afforded 2-(methyl 6-deoxy-2,3-O-isopropylidene-alpha-D-mannofuranosid-6-yl)-1,3-dithiane (2). Treatment of 2 with n-butyllithium then alkyl iodide gave the corresponding 2-(methyl 5-O-alkyl-6-deoxy-2,3-O-isopropylidene-alpha-D-mannofuranosid-6-yl)-1,3-dithiane. Reaction of 2 with n-butyllithium and 5,6-cyclic sulfate 1 furnished 2-[methyl 6-deoxy-2,3-O-isopropylidene-5-O-(methyl 6-deoxy-2,3-O-isopropylidene-alpha-D-manno-furanosid-6-yl)-alpha-D-mannofuranosid-6-yl]-1,3-dithiane. 2-(Methyl 6-deoxy-2,3-O-isopropylidene-5-O-methyl-alpha-D-mannofuranosid-6-yl)-1,3-dithiane was converted into the lithiated anion, which after treatment with alkyl halide afforded the corresponding 2-alkyl-C-(methyl 6-deoxy-2,3-O-isopropylidene-5-O-methyl-alpha-D-mannofuranosid-6-yl)-1,3-dithiane. In a Path B, 5,6-cyclic sulfate 1 reacted with 2-alkyl-2-lithio-1,3-dithiane derivatives, which led after acidic hydrolysis to 2-alkyl-2-(methyl 6-deoxy-2,3-O-isopropylidene-alpha-D-mannofuranosid-6-yl)-1,3-dithiane accompanied by methyl 6-deoxy-2,3-O-isopropylidene-alpha-D-lyxo-hexofuranos-5-uloside as the by-product. This methodology was applied to synthesize 2-(methyl 6-deoxy-2,3-O-isopropylidene-5-O-methyl-alpha-D-mannofuranosid-6-yl)-2-(methyl 6-deoxy-2,3-O-isopropylidene-alpha-D-mannofuranosid-6-yl)-1,3-dithiane. (C) 2000 Elsevier Science Ltd. All rights reserved.
• KLEIN, P. A. M. VAN DER;BOONS, G. J. P. H.;VEENEMAN, G. H.;MAREL, G. A. V+, TETRAHEDRON LETT., 30,(1989) N0, C. 5477-5480
  作者：KLEIN, P. A. M. VAN DER、BOONS, G. J. P. H.、VEENEMAN, G. H.、MAREL, G. A. V+

  DOI：——

  日期：——
• An efficient route to 3-deoxy-d-manno-2-octulosonic acid (KDO) derivatives via a 1,4-cyclic sulfate approach
  作者：P.A.M. van der Klein、G.J.P.H. Boons、G.H. Veeneman、G.A. van der Marel、J.H. van Boom

  DOI：10.1016/s0040-4039(01)80598-0

  日期：1989.1