isopropenyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-α,β-D-galactopyranosyl carbonate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: isopropenyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-α,β-D-galactopyranosyl carbonate
• 英文别名: [(3R,4R,5R,6R)-3-azido-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl] prop-1-en-2-yl carbonate
• 化学式: C₃₁H₃₃N₃O₇
• 分子量: 559.619
• InChiKey: VOJCBDHHYPZEPA-MPUKMYDRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  41
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  86.8
• 氢给体数：
  0
• 氢受体数：
  9

上下游信息

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	methyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-galactopyranosyl-β-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside	139608-16-5	C55H59N3O10	922.088
  ——	methyl 4-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranosyl)-2,3,6-tri-O-benzyl-α-D-glucopyranoside	139608-15-4	C55H59N3O10	922.088

反应信息

• 作为反应物：
  描述：

  甲基2,3,6-三-O-苄基-ALPHA-D-吡喃葡萄糖苷 、 isopropenyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-α,β-D-galactopyranosyl carbonate 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 methyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-galactopyranosyl-β-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside 、 methyl 4-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranosyl)-2,3,6-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Isopropenyl glycosides and congeners as novel classes of glycosyl donors: theme and variations

  摘要：

  Isopropenyl glycosides (i.e., 10 and 11) have been synthesized in high yields by reacting the corresponding anomeric acetates with the Tebbe reagent. These compounds undergo glycosylation with primary or secondary carbohydrate alcohols in the presence of trimethylsilyl triflate or boron trifluoride etherate, probably via a mixed acetal glycoside intermediate. On the basis of this principle, a quite efficient glycosylation of monosaccharide hemiacetal donors (i.e., 1, 7, and 9) with acceptors bearing an isopropenyl ether function at a primary or secondary position (i.e., 18 and 21) has been developed. Also investigated were the glycosylating properties of isopropenyl glucosyl and galactosyl carbonates (i.e., 12-15), easily prepared from the corresponding hemiacetals, toward sugar alcohols. In each case, the beta-selective synthesis of disaccharides from donors having nonparticipating groups at C-2 was ensured by the use of acetonitrile, at low temperature, as the solvent.

  DOI：

  10.1021/ja00042a010

文献信息

• Isopropenyl glycosides and congeners as novel classes of glycosyl donors: theme and variations
  作者：Alberto Marra、Jacques Esnault、Alain Veyrieres、Pierre Sinay

  DOI：10.1021/ja00042a010

  日期：1992.7

  Isopropenyl glycosides (i.e., 10 and 11) have been synthesized in high yields by reacting the corresponding anomeric acetates with the Tebbe reagent. These compounds undergo glycosylation with primary or secondary carbohydrate alcohols in the presence of trimethylsilyl triflate or boron trifluoride etherate, probably via a mixed acetal glycoside intermediate. On the basis of this principle, a quite efficient glycosylation of monosaccharide hemiacetal donors (i.e., 1, 7, and 9) with acceptors bearing an isopropenyl ether function at a primary or secondary position (i.e., 18 and 21) has been developed. Also investigated were the glycosylating properties of isopropenyl glucosyl and galactosyl carbonates (i.e., 12-15), easily prepared from the corresponding hemiacetals, toward sugar alcohols. In each case, the beta-selective synthesis of disaccharides from donors having nonparticipating groups at C-2 was ensured by the use of acetonitrile, at low temperature, as the solvent.