methyl 4,6-O-benzylidene-2,3-di-O-benzyl-α-D-altropyranoside | 99212-27-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: methyl 4,6-O-benzylidene-2,3-di-O-benzyl-α-D-altropyranoside
• CAS: 99212-27-8
• 化学式: C₂₈H₃₀O₆
• 分子量: 462.543
• InChiKey: CVHUOBYFXKHVJR-GTMDKHCLSA-N

物化性质

• 沸点：
  585.4±50.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.64
• 重原子数：
  34.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 4,6-O-benzylidene-2,3-di-O-benzyl-α-D-altropyranoside 在 吡啶 、 咪唑 、 碘 、 三苯基膦 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 18.25h， 生成 methyl 4-O-benzoyl-2,3-di-O-benzyl-6-deoxy-6-iodo-α-D-altropyranoside
  参考文献：
  名称：

  Synthesis of A Novel Sialyl Lewis X Analogue Containing A Pyrrolidine in Place ofN-Acetyl Glucosamine

  摘要：

  The synthesis of the new sialyl Lewis X analogue, 4-O-(alpha-L-fucopyranosyl)-3-O-(3-O-sodium sulfonato-beta-D-galactopyranosyl)-(2S,3R, 4R)-2-ethyl-3,4-dihydroxypyrrolidine 2 has been achieved. The N-acetyl glucosamine unit of natural Lewis X has been replaced by a rigid 3R/4R-dihydroxylated pyrrolidine 12. This one has been synthezised from the methyl 4-O-benzoyl-2,3-di-O-benzyl-6-deoxy-6-iodo-alpha-D-altropyranoside sugar precursor 10 using the Ganem/Bernotas one-pot elimination-reductive amination ring contraction reaction. The (2S,3R,4R)-1-benzyloxycarbonyl-3,4-dihydroxy-2-ethylpyrrolidine 12 obtained was subsequently regioselectively glycosylated, using 2,3,4-tri-O-benzyl-alpha-L-fucopyranosyl fluoride and 2,3,4,6-tetra-O-benzoyl-beta-D-galactopyranosyl bromide as glycosyl donors. Disaccharide containing pyrrolidine 21 was finally transformed into the target O-sulfated analog 2, after regioselective sulfation and usual deprotection.

  DOI：

  10.1080/07328300008544095
• 作为产物：
  描述：

  氯化苄 、 methyl 2,3-anhydro-4,6-benzylidene-α-D-allopyranoside 在 sodium hydroxide 作用下， 生成 methyl 4,6-O-benzylidene-2,3-di-O-benzyl-α-D-altropyranoside
  参考文献：
  名称：

  Total synthesis of antibiotic hygromycin A

  摘要：

  The first total synthesis of the antibiotic (-)-hygromycin A (1) has been achieved by a coupling reaction of the sugar moiety (2) and the cyclitol moiety (3). Both components were synthesized in homochiral forms starting from D-glucose. This synthesis fully confirmed the unique structure of 1, which is much different from other usual aminocyclitol antibiotics.

  DOI：

  10.1021/jo00009a009

文献信息

• Synthesis from<scp>D</scp>-glucose of 1,5-dideoxy-1,5-imino-<scp>L</scp>-fucitol, a potent α-<scp>L</scp>-fucosidase inhibitor
  作者：George W. J. Fleet、Antony N. Shaw、Stephen V. Evans、Linda E. Fellows

  DOI：10.1039/c39850000841

  日期：——

  1,5-Dideoxy-1,5-imino-L-fucitol (1), synthesised from methyl α-D-glucopyranoside, is a potent competitive inhibitor of the hydrolysis of p-nitrophenyl α-L-fucopyranoside catalysed by α-L-fucosidase (ex. bovine epididymis) causing 50% inhibition of enzymic activity at 2.5 × 10–8M.

  1,5-二脱氧-1,5-亚氨基-L-岩藻糖醇（1），由甲基α-D-吡喃葡萄糖苷合成，是一种强效的竞争性抑制剂，能够抑制α-L-岩藻糖苷酶（如牛附睾中的）催化对硝基苯α-L-岩藻糖苷的水解，在2.5×10⁻⁸M浓度下导致酶活性的50%抑制。