1-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-α-D-glucopyranosyl)-2-propene | 259136-58-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-α-D-glucopyranosyl)-2-propene
• 英文别名: (2R,3S,4R,5R,6R)-4-phenylmethoxy-6-(phenylmethoxymethyl)-2-prop-2-enyl-5-[(2S,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxan-3-ol
• CAS: 259136-58-8
• 化学式: C₅₇H₆₂O₁₀
• 分子量: 907.113
• InChiKey: HIVXDVXGTQNIGG-HPVZZYENSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  67
• 可旋转键数：
  24
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  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 lithium aluminium tetrahydride 、 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 22.0h， 生成 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：

  在 碘 、 溶剂黄146 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 21.0h， 以14.8 g的产率得到1-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-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

文献信息

• Conversion of Lactose into Mimics ofN-Acetyllactosamine
  作者：Luigi Lay、Laura Cipolla、Barbara La Ferla、Francesco Peri、Francesco Nicotra

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

  日期：1999.12

  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.