3,4,6-tri-O-acetyl-1,2-O-<(S)-ethylidene>-β-D-mannopyranose | 83289-94-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 3,4,6-tri-O-acetyl-1,2-O-<(S)-ethylidene>-β-D-mannopyranose
• 英文别名: (S)-3,4,6-tri-O-acetyl-1,2-O-ethylidene-β-D-mannopyranose；3,4,6-Tri-O-acetyl-1,2-[(S)-ethylidene]-beta-D-mannopyranose；[(2S,3aS,5R,6R,7S,7aS)-6,7-diacetyloxy-2-methyl-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-5-yl]methyl acetate
• CAS: 83289-94-5
• 化学式: C₁₄H₂₀O₉
• 分子量: 332.307
• InChiKey: NBWFYJVPTWVPKZ-ZSOGLFGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2,3,4,6-四-O-乙酰基-1-溴-Alpha-D-甘露糖 在 偶氮二异丁腈 、 sodium cyanoborohydride 作用下， 以 叔丁醇 为溶剂， 反应 6.5h， 以54%的产率得到3,4,6-tri-O-acetyl-1,2-O-<(S)-ethylidene>-β-D-mannopyranose
  参考文献：
  名称：

  NaBH3CN and other systems as substitutes of tin and silicon hydrides in the light or heat-initiated reduction of halosugars: a tunable access to either 2-deoxy sugars or 1,5-anhydro-itols

  摘要：

  UV light-promoted reduction of acetobromoglucose by NaBH3CN in t-BuOH afforded 1,3,4,6-tetra-O-acetyl-2-deoxy-alpha-D-arabino-hexopyranose in high yield and purity, via a Surzur-Tanner rearrangement, while, with 10 mol % thiophenol added, acetylated 1,5-anhydro-D-glucitol was cleanly obtained. Such tin-free and mild reductions, presumed to proceed via radical pathways, were more efficient with NaBH3CN compared to NaBH4 or NaBD4, and do not occur with acetochloroglucose. Similar reductions to 1,3,4,6-tetra-O-acetyl-2-deoxy-alpha-D-arabino-hexopyranose were achieved upon heating to 80 degrees C t-BuOH or CH3CN solutions of NaBH3CN and AIBN, but with a lower selectivity due to competing ionic reactions. With other pyranosyl bromides, reductions by NaBH3CN could be tuned similarly (D-galacto), but some (D-manno, 5-thio-D-xylo) gave mainly or exclusively 1,5-anhydro-itols. Other conditions, or reagents promoting SET process, afforded also reduced products, but with lower rates or selectivities. Primary iodides were reduced readily with NaBH3CN under UV light. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.09.032

文献信息

• A convenient synthesis of 1,2-O-benzylidene and 1,2-O-ethylidene derivatives of carbohydrates
  作者：Vitali I. Betaneli、Michael V. Ovchinnikov、Leon V. Backinowsky、Nikolay K. Kochetkov

  DOI：10.1016/s0008-6215(00)80547-9

  日期：1982.9