6-O-dimethoxytrityl-2,3,4-tri-O-benzyl-D-glucopyranose

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 6-O-dimethoxytrityl-2,3,4-tri-O-benzyl-D-glucopyranose
• 英文别名: (3R,4S,5R,6R)-6-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-3,4,5-tris(phenylmethoxy)oxan-2-ol
• 化学式: C₄₈H₄₈O₈
• 分子量: 752.904
• InChiKey: XPBDJWXSBQGQFE-VEWVWOIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  56
• 可旋转键数：
  17
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  84.8
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  6-O-dimethoxytrityl-2,3,4-tri-O-benzyl-D-glucopyranose 在 ytterbium(III) triflate sodium hydride 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 24.0h， 生成 2,3,4-tri-O-benzyl-6-O-di(4-methoxy)trityl-α-D-glucopyranosyl-(1->6)-1,2:3,4-O-diisopropylidene-α-D-galactopyranose
  参考文献：
  名称：

  An approach to the highly stereocontrolled synthesis of α-glycosides. Compatible use of the very acid labile dimethoxytrityl protecting group with Yb(OTf)3-promoted glycosidation

  摘要：

  The very acid labile dimethoxytrityl group is demonstrated to survive Yb(OTf)(3)-promoted glycosidations with N-phenyl trifluoroacetimidates as the donors. In addition, the installation of this sterically demanding protecting group at the primary position of the donor allows the achievement of a very high selectivity in the synthesis of alpha-glycosides with a variety of saccharidic acceptors. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01541-7
• 作为产物：
  描述：

  1,6-二-O-乙酰基-2,3,4-三-O-苄基-beta-D-吡喃葡萄糖 在 4-二甲氨基吡啶 TEA 、 sodium methylate 作用下， 以 吡啶 、 甲醇 为溶剂， 生成 6-O-dimethoxytrityl-2,3,4-tri-O-benzyl-D-glucopyranose
  参考文献：
  名称：

  An approach to the highly stereocontrolled synthesis of α-glycosides. Compatible use of the very acid labile dimethoxytrityl protecting group with Yb(OTf)3-promoted glycosidation

  摘要：

  The very acid labile dimethoxytrityl group is demonstrated to survive Yb(OTf)(3)-promoted glycosidations with N-phenyl trifluoroacetimidates as the donors. In addition, the installation of this sterically demanding protecting group at the primary position of the donor allows the achievement of a very high selectivity in the synthesis of alpha-glycosides with a variety of saccharidic acceptors. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01541-7

文献信息

• Rapid glycosylations under extremely mild acidic conditions. Use of ammonium salts to activate glycosyl phosphites via P-protonation
  作者：Fumiko Matsumura、Shiro Tatsumi、Natsuhisa Oka、Takeshi Wada

  DOI：10.1016/j.carres.2010.03.009

  日期：2010.6

  Trifluoromethanesulfonic acid salts of tertiary amines were employed as extremely mild acidic activators for rapid glycosylations. Glycosyl phosphite triesters bearing an acid-labile 4,4'-dimethoxytrityl (DMTr) group for transient protection worked as glycosyl donors effectively in the presence of the activators to afford the corresponding disaccharides in good yields without loss of the DMTr group

  叔胺的三氟甲磺酸盐用作快速糖基化的极温和的酸性活化剂。在活化剂的存在下，带有酸不稳定的4,4'-二甲氧基三苯甲基（DMTr）基团的糖基亚磷酸三酯具有有效的糖基供体作用，能够以良好的收率提供相应的二糖，而不会损失DMTr基团。
• An approach to the highly stereocontrolled synthesis of α-glycosides. Compatible use of the very acid labile dimethoxytrityl protecting group with Yb(OTf)3-promoted glycosidation
  作者：Matteo Adinolfi、Alfonso Iadonisi、Marialuisa Schiattarella

  DOI：10.1016/s0040-4039(03)01541-7

  日期：2003.8

  The very acid labile dimethoxytrityl group is demonstrated to survive Yb(OTf)(3)-promoted glycosidations with N-phenyl trifluoroacetimidates as the donors. In addition, the installation of this sterically demanding protecting group at the primary position of the donor allows the achievement of a very high selectivity in the synthesis of alpha-glycosides with a variety of saccharidic acceptors. (C) 2003 Elsevier Ltd. All rights reserved.