3-O-acetyl-4-O-benzyl-2,6-dideoxy-α-D-mannopyranose | 1161782-30-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-acetyl-4-O-benzyl-2,6-dideoxy-α-D-mannopyranose
• 英文别名: [(2R,3R,4R,6S)-6-hydroxy-2-methyl-3-phenylmethoxyoxan-4-yl] acetate
• CAS: 1161782-30-4
• 化学式: C₁₅H₂₀O₅
• 分子量: 280.321
• InChiKey: KNIOBAQHGABOJZ-QPKOPYBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.63
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  [(2R,3R,4R)-2-methyl-3-phenylmethoxy-3,4-dihydro-2H-pyran-4-yl] acetate 、 溶剂黄146 在 三苯基膦氢溴酸盐 作用下， 以 二氯甲烷 为溶剂， 生成 3-O-acetyl-4-O-benzyl-2,6-dideoxy-β-D-mannopyranose 、 3-O-acetyl-4-O-benzyl-2,6-dideoxy-α-D-mannopyranose 、 1,3-di-O-acetyl-4-O-benzyl-2,6-dideoxy-β-D-mannopyranose 、 1,3-di-O-acetyl-4-O-benzyl-2,6-dideoxy-α-D-glucose
  参考文献：
  名称：

  Synthesis of orthogonally protected d-olivoside, 1,3-di-O-acetyl-4-O-benzyl-2,6-dideoxy-d-arabinopyranose, as a C-glycosyl donor

  摘要：

  1,3-Di-O-acetyl-4-O-benzyl-2,6-dideoxy-D-arabinopyranose (11) was synthesised from thiophenyl alpha-D-mannopyranoside (21) in an eight-step sequence. Tosylation of 21 and subsequent reaction with 2,2-dimethoxypropane gave tosylate 22, which upon treatment with lithium aluminium hydride furnished 6-deoxy glycoside 24 and by-product thiophenyl 6-deoxy-2-O-isopropyl-alpha-D-arabinopyranoside. The X-ray crystal structure of the latter was determined. Benzylation of the 4-hydroxyl group of 24 and Subsequent protecting group manipulation gave D-rhamnosyl bromide 29, which on treatment with zinc-copper couple gave the orthogonally protected D-rhamnal 30. Triphenylphosphine hydrogen bromide catalysed addition of acetic acid to 30 furnished the target molecule 11. The scandium(III) triflate promoted reaction of 11 and 2-naphthol gave the corresponding C-glycoside 36 in 86% yield. Crown Copyright (C) 2009 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.03.092