甲基2-O-烯丙基-3,4-二-O-苄基吡喃己糖苷 | 210297-56-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 甲基2-O-烯丙基-3,4-二-O-苄基吡喃己糖苷
• 英文名称: methyl 2-O-allyl-3,4-di-O-benzyl-α-D-mannopyranoside
• 英文别名: Methyl 2-O-allyl-3,4-DI-O-benzyl-A-D-mannopyranoside；[(2R,3R,4S,5S,6S)-6-methoxy-3,4-bis(phenylmethoxy)-5-prop-2-enoxyoxan-2-yl]methanol
• CAS: 210297-56-6
• 化学式: C₂₄H₃₀O₆
• 分子量: 414.499
• InChiKey: GBXPCZLNEKGTHT-DJCPXJLLSA-N

物化性质

• 溶解度：
  可溶于氯仿、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  甲基2-O-烯丙基-3,4-二-O-苄基吡喃己糖苷 在 草酰氯 、 二甲基亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (2S,3S,4S,5S,6S)-5-Allyloxy-3,4-bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-carbaldehyde
  参考文献：
  名称：

  Five monophosphates of methyl l-glycero-α-d-manno-heptopyranoside: synthesis, hydrolysis and migrations

  摘要：

  From suitably protected methyl alpha-D-mannopyranosides five methyl L-glycero-alpha-D-manno-heptopyranosides were synthesized by the one-carbon-atom chain elongation at C-6 and converted to five monophosphates (1-5) having the PO(OH)(2) group at O-2, -3, -4, -6 and -7. Compounds 1-5 were exposed to acidic and basic hydrolytic conditions used in lipopolysaccharide analysis and the products and their proportion were determined. Under acidic conditions, besides hydrolysis of the glycoside, migrations and hydrolytic cleavage of the phosphate residue were found. Under basic conditions the phosphates were stable. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00037-8
• 作为产物：
  描述：

  甲基2-O-烯丙基-3-O-苄基-4,6-O-亚苄基吡喃己糖苷 在 lithium aluminium tetrahydride 、 三氯化铝 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 0.75h， 以96%的产率得到甲基2-O-烯丙基-3,4-二-O-苄基吡喃己糖苷
  参考文献：
  名称：

  Five monophosphates of methyl l-glycero-α-d-manno-heptopyranoside: synthesis, hydrolysis and migrations

  摘要：

  From suitably protected methyl alpha-D-mannopyranosides five methyl L-glycero-alpha-D-manno-heptopyranosides were synthesized by the one-carbon-atom chain elongation at C-6 and converted to five monophosphates (1-5) having the PO(OH)(2) group at O-2, -3, -4, -6 and -7. Compounds 1-5 were exposed to acidic and basic hydrolytic conditions used in lipopolysaccharide analysis and the products and their proportion were determined. Under acidic conditions, besides hydrolysis of the glycoside, migrations and hydrolytic cleavage of the phosphate residue were found. Under basic conditions the phosphates were stable. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00037-8

文献信息

• Factors Affecting Stereocontrol during Glycosidation of 2,3-Oxazolidinone-Protected 1-Tolylthio-<i>N</i>-acetyl-<scp>d</scp>-glucosamine
  作者：Peng Wei、Robert J. Kerns

  DOI：10.1021/jo047812o

  日期：2005.5.1

  It is demonstrated that a ring-fused 2,3-oxazolidinone-protected derivative of 1-tolylthio-N-acetyl-D-glucosamine undergoes high-yield glycosidation under mild donor activation conditions. Stereoselective formation of alpha-linked or beta-linked glycosides is dependent on reactivity of acceptor alcohols, where rate of glycosidation correlates to stereochemical outcome. Evidence for the role of glycosyl triflate intermediates and the N-acetyl substituent of the 2N,3O-oxazolidinone ring in stereochemical control is presented.