(2S*,3S*,4S*,6S*)-6-benzyloxymethyl-2-methoxy-tetrahydropyran-3,4-diol

• 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: (2S*,3S*,4S*,6S*)-6-benzyloxymethyl-2-methoxy-tetrahydropyran-3,4-diol
• 英文别名: (2R,3R,4R,6R)-2-methoxy-6-(phenylmethoxymethyl)oxane-3,4-diol
• 化学式: C₁₄H₂₀O₅
• 分子量: 268.31
• InChiKey: TTWMSDLRSYCOKL-AAVRWANBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S*,3S*,4S*,6S*)-6-benzyloxymethyl-2-methoxy-tetrahydropyran-3,4-diol 在 4 A molecular sieve 、 硫酸 、 sodium hydride 、 溶剂黄146 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 48.83h， 生成 (3S*,4S*,6S*)-3,4-bisbenzyloxy-6-benzyloxymethyltetrahydropyran-2-one
  参考文献：
  名称：

  Preparation and reactions of 2-allyl-5-deoxymannose derivatives

  摘要：

  Reaction of Danishefsky diene with benzyloxyethanal led to a pyrone which was transformed in 4-6 steps to different 5-deoxymannose derivatives, useful intermediates for the synthesis of natural product such as hemibrevetoxin. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00150-3
• 作为产物：
  描述：

  (R)-苄氧甲基环氧乙烷 在 吡啶 、 titanium(IV) isopropylate 、 四氧化锇 、 三氟甲磺酸三甲基硅酯 、 TEA 、 镍 、 N-甲基吗啉氧化物 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 丙酮 、 叔丁醇 为溶剂， 反应 35.08h， 生成 (2S*,3S*,4S*,6S*)-6-benzyloxymethyl-2-methoxy-tetrahydropyran-3,4-diol
  参考文献：
  名称：

  Synthesis of 4-Deoxy-l-(and d-)hexoses from Chiral Noncarbohydrate Building Blocks

  摘要：

  4-Deoxy-L-hexoses were synthesized starting from our previously reported reagent 1 and (R)-benzyl glycidyl ether, which led in few steps to a substituted dihydropyran 6. The stereocontrolled hydroxylation of the latter afforded the corresponding 4-deoxy-L-hexoses 7a, 9, and 11. The same procedure, starting from (S)-benzyl glycidyl ether, enabled the preparation of their D-series enantiomers.

  DOI：

  10.1021/jo0493774

文献信息

• Saleh, Twana; Rousseau, Gerard, Synlett, 1999, # 5, p. 617 - 619
  作者：Saleh, Twana、Rousseau, Gerard

  DOI：——

  日期：——
• Preparation and reactions of 2-allyl-5-deoxymannose derivatives
  作者：Twana Saleh、Gérard Rousseau

  DOI：10.1016/s0040-4020(02)00150-3

  日期：2002.4

  Reaction of Danishefsky diene with benzyloxyethanal led to a pyrone which was transformed in 4-6 steps to different 5-deoxymannose derivatives, useful intermediates for the synthesis of natural product such as hemibrevetoxin. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Synthesis of 4-Deoxy-<scp>l</scp>-(and <scp>d</scp>-)hexoses from Chiral Noncarbohydrate Building Blocks
  作者：Romualdo Caputo、Mauro De Nisco、Pasquale Festa、Annalisa Guaragna、Giovanni Palumbo、Silvana Pedatella

  DOI：10.1021/jo0493774

  日期：2004.10.1

  4-Deoxy-L-hexoses were synthesized starting from our previously reported reagent 1 and (R)-benzyl glycidyl ether, which led in few steps to a substituted dihydropyran 6. The stereocontrolled hydroxylation of the latter afforded the corresponding 4-deoxy-L-hexoses 7a, 9, and 11. The same procedure, starting from (S)-benzyl glycidyl ether, enabled the preparation of their D-series enantiomers.