(2R,4R,5S,6R)-2-Allyl-4-benzyloxy-6-benzyloxymethyl-5-((2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-dihydro-pyran-3-one O-methyl-oxime | 259136-60-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,4R,5S,6R)-2-Allyl-4-benzyloxy-6-benzyloxymethyl-5-((2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-dihydro-pyran-3-one O-methyl-oxime
• CAS: 259136-60-2
• 化学式: C₅₈H₆₃NO₁₀
• 分子量: 934.139
• InChiKey: FQHCCSSPXLUGIG-HZMNEILYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.22
• 重原子数：
  69.0
• 可旋转键数：
  25.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  104.66
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (2R,4R,5S,6R)-2-Allyl-4-benzyloxy-6-benzyloxymethyl-5-((2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-dihydro-pyran-3-one O-methyl-oxime 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以1.95 g的产率得到1-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-2-amino-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2-propene
  参考文献：
  名称：

  Conversion of Lactose into Mimics ofN-Acetyllactosamine

  摘要：

  The alpha-C-Glycoside of N-acetyllactosamine 8 was synthesised from lactose by acetylation, conversion into the allyl alpha-C-glycoside 4, exchanging the protecting groups for benzyl ethers, selective deprotection at the gluco-C-2 by iodocyclisation-reductive elimination, and conversion of the free hydroxyl group into an acetamido group by oxidation, oximation, stereoselective reduction and acetylation. Isomerization of the C-glycosidic appendage by conversion into a 2-oxypropyl group and treatment with base gave, after acetylation, the beta-C-glycoside of N-acetyllactosamine 11.

  DOI：

  10.1002/(sici)1099-0690(199912)1999:12<3437::aid-ejoc3437>3.0.co;2-0
• 作为产物：
  描述：

  1-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-α-D-glucopyranosyl)-2-propene 在 4 A molecular sieve 、 sodium acetate 、 乙酸酐 、 二甲基亚砜 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 6.0h， 生成 (2R,4R,5S,6R)-2-Allyl-4-benzyloxy-6-benzyloxymethyl-5-((2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-dihydro-pyran-3-one O-methyl-oxime
  参考文献：
  名称：

  Conversion of Lactose into Mimics ofN-Acetyllactosamine

  摘要：

  The alpha-C-Glycoside of N-acetyllactosamine 8 was synthesised from lactose by acetylation, conversion into the allyl alpha-C-glycoside 4, exchanging the protecting groups for benzyl ethers, selective deprotection at the gluco-C-2 by iodocyclisation-reductive elimination, and conversion of the free hydroxyl group into an acetamido group by oxidation, oximation, stereoselective reduction and acetylation. Isomerization of the C-glycosidic appendage by conversion into a 2-oxypropyl group and treatment with base gave, after acetylation, the beta-C-glycoside of N-acetyllactosamine 11.

  DOI：

  10.1002/(sici)1099-0690(199912)1999:12<3437::aid-ejoc3437>3.0.co;2-0