isopropenyl 2,3,4,6-tetra-O-benzyl-α,β-D-galactopyranoside | 136399-62-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: isopropenyl 2,3,4,6-tetra-O-benzyl-α,β-D-galactopyranoside
• 英文别名: (2R,3S,4S,5R)-3,4,5-tris(phenylmethoxy)-2-(phenylmethoxymethyl)-6-prop-1-en-2-yloxyoxane
• CAS: 136399-62-7
• 化学式: C₃₇H₄₀O₆
• 分子量: 580.721
• InChiKey: WDFOSQZERHEEHW-HRKBRENZSA-N

物化性质

• 沸点：
  688.9±55.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  43
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Dithiocarbonic acid S-((2S,4aR,6S,7R,8R,8aR)-7-azido-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl) ester O-ethyl ester 、 isopropenyl 2,3,4,6-tetra-O-benzyl-α,β-D-galactopyranoside 生成 O-ethyl S-<2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-β-D-galactopyranosyl> dithiocarbonate
  参考文献：
  名称：

  一类新颖的糖基供体：2-叠氮基-2-脱氧-D-吡喃半乳糖基衍生物的端基S-黄原酸酯

  摘要：

  通过相应半乳糖（1,5-脱水-2-脱氧-D- lyxo）的两步叠氮蒽并化反应，可以轻松制备各种取代的O-乙基S-（2-叠氮基-2-脱氧-D-吡喃半乳糖基）二硫代碳酸酯。（-hex-1-enitols）。它们是有效的糖基供体，用于立体选择性地合成具有生物学重要性的含半乳糖胺的寡糖的保护前体。

  DOI：

  10.1016/s0040-4020(01)87127-1

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.