(E)-5,6-didehydro-5,6-dideoxy-3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-heptodialo-1,4-furanose | 72383-09-6

• 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: (E)-5,6-didehydro-5,6-dideoxy-3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-heptodialo-1,4-furanose
• 英文别名: (E)-3-[(3aR,5R,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]prop-2-enal
• CAS: 72383-09-6
• 化学式: C₁₇H₂₀O₅
• 分子量: 304.343
• InChiKey: HPYJVRAHGPIJEG-CBIXMBKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-5,6-didehydro-5,6-dideoxy-3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-heptodialo-1,4-furanose 在 diisobutylaluminum hydride 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以69%的产率得到(E)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-5-eno-1,4-furanose
  参考文献：
  名称：

  通过烯烃糖的渗透作用合成一些七碳糖

  摘要：

  摘要6,7-二脱氧-1,2：3,4-二-O-异亚丙基-α-d-半乳糖-庚-6-庚烷（10），5,6-二脱氧- 1,2-O-异亚丙基-α-d-二甲苯基-六-5-烯呋喃糖，（E）-和（Z）-3-O-苄基-5,6-二-脱氧-1,2-O-异亚丙基-α-d-木酮-庚5-呋喃呋喃糖（分别为20和27），甲基（Z）-3- O-苄基-5,6-二脱氧-1,2- O-异亚丙基-α-d-木酮-庚5-呋喃呋喃酸酯（26），（E）-3- O-苄基5,6-二脱氧-1,2-O-异亚丙基-α-d-核糖-庚基5-呋喃呋喃糖，苄基（E） -和（Z）-5,6-二脱氧-2,3-O-异亚丙基-α-d-lyxo-hept-5-enofuranoside（分别为46和50）和甲基[苄基（Z）-5,6已经研究了-二-脱氧-2，3-O-异亚丙基-α-d-lyxo-庚基-5-异呋喃糖苷]尿酸酯（49）。这样的氧化导致令人满意地合成1-甘油-

  DOI：

  10.1016/0008-6215(86)80004-0
• 作为产物：
  描述：

  (Z)-N-benzyl-(3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranos-5-ylidene)amine N-oxide 在 碳酸氢钠 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 28.5h， 生成 (E)-5,6-didehydro-5,6-dideoxy-3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-heptodialo-1,4-furanose
  参考文献：
  名称：

  Higher glycosamino acid precursors: C7 and C8 aminodialdoses via regio- and stereoselective [3+2] cycloaddition of vinyl trimethylsilane to C-glycosyl nitrones

  摘要：

  Protected C-7 and C-8 aminodialdoses were prepared stereoselectively from readily available C-5 and C-6 monosaccharide N-benzyl nitrones, by regio- and diastereoselective 1,3-dipolar cycloaddition reactions with vinyl trimethylsilane, followed by acetyl chloride-mediated cleavage of the 5-(trimethylsilyl)isoxazolidine formed. The cycloaddition reaction took place in moderate to good global yields (67-74%); estimation of diastereoselectivities from isolated yields showed total endo preference for the reaction of the D-galacto configured nitrone and high endo preference for the D-ribo analogue, but exo preference for the D-Xylo configured substrate. Attack on the re face of the nitrone was predominant in all cases. The absolute configuration of one of the protected 3-(alpha-D-galacto-pentopyranos-5-yl)isoxazolidine products was assigned by X-ray crystallographic analysis, allowing correlation of the configuration at the new stereogenic centre in the corresponding aminodialdose. For non-crystalline isoxazolidines, configurations were assigned on the basis of NOESY experiments and/or chemical correlation. Combined yields of aminodialdoses coming from isoxazolidines having identical configuration at C(3) sometimes reached high values (up to 90%). These compounds are precursors of higher-chain glycosamino acids. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(02)00543-8

文献信息

• Stereochemistry of osmylation of chiral dienes: diastereoselective synthesis of octitols
  作者：Kesavaram Narkunan、Madhavarao Nagarajan

  DOI：10.1039/c39940001705

  日期：——

  The synthesis of higher sugars by hydroxylation of sugar derived dienes 2 and 4 using OsO4–NMO is described.

  描述了使用OsO 4 -NMO通过糖衍生的二烯2和4的羟基化合成高级糖。