methyl 6-(S)-²H-6-O-<(R)-1-carboxyethyl>-2,3,4-tri-O-benzyl-α-D-galactopyranoside | 220901-59-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-(S)-²H-6-O-<(R)-1-carboxyethyl>-2,3,4-tri-O-benzyl-α-D-galactopyranoside
• CAS: 220901-59-7
• 化学式: C₃₁H₃₆O₈
• 分子量: 537.614
• InChiKey: OHXKIJOEADFKFT-UJLQBVNHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  39.0
• 可旋转键数：
  14.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  92.68
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl 6-(S)-²H-6-O-<(R)-1-carboxyethyl>-2,3,4-tri-O-benzyl-α-D-galactopyranoside 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 25.0h， 以98%的产率得到methyl 6-(S)-²H-6-O-<(R)-1-carboxyethyl>-α-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of site-specific deuterium substituted methyl 6-O-[(R)- and (S)-1-carboxyethyl]-α-d-galactopyranoside and conformational analysis thereof based on J couplings

  摘要：

  Methyl 6-(S)-H-2-6-O-[(R)- and (S)-1-carboxyethyl]-alpha-D-galactopyranoside have been synthesized from 6-(S)-H-2-1,6-anhydro-beta-D-gaiactopyranoside. Conformational analysis of the exocyclic dihedral angles has been performed based on (3)J(H,H) and (3)J(C,H) coupling constants of the title compounds together with their non-deuterated counterparts. The omega dihedral angle (O-5-C-5-C-6-O-6) can be described by a conformational equilibrium where the order of conformers is gauche-trans > trans-gauche > gauche-gauche, i.e., the same as for galactose but with a different population distribution. The C-5-C-6-O-6-C-2' torsion populates only the gauche states, as deduced from J couplings. This is at variance with previous Langevin dynamics simulations in which the proportion of the trans state is significant. For the C-6-O-6-C-2'-H2' torsion an equal population of the three staggered conformers is compatible with experimental data, although previous simulations have indicated gauche conformers to be preferred. Since about half the number of the possible conformational states for the major degrees of freedom are significantly populated, as corroborated by experimental data, the flexibility of the substituting l-carboxyethyl group is large. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00240-7
• 作为产物：
  描述：

  6-(S)-²H-1,6-di-O-acetyl-2,3,4-tri-O-benzyl-D-galactopyranoside 在 盐酸 、 sodium hydride 作用下， 以 1,4-二氧六环 为溶剂， 反应 26.0h， 生成 methyl 6-(S)-²H-6-O-<(R)-1-carboxyethyl>-2,3,4-tri-O-benzyl-α-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of site-specific deuterium substituted methyl 6-O-[(R)- and (S)-1-carboxyethyl]-α-d-galactopyranoside and conformational analysis thereof based on J couplings

  摘要：

  Methyl 6-(S)-H-2-6-O-[(R)- and (S)-1-carboxyethyl]-alpha-D-galactopyranoside have been synthesized from 6-(S)-H-2-1,6-anhydro-beta-D-gaiactopyranoside. Conformational analysis of the exocyclic dihedral angles has been performed based on (3)J(H,H) and (3)J(C,H) coupling constants of the title compounds together with their non-deuterated counterparts. The omega dihedral angle (O-5-C-5-C-6-O-6) can be described by a conformational equilibrium where the order of conformers is gauche-trans > trans-gauche > gauche-gauche, i.e., the same as for galactose but with a different population distribution. The C-5-C-6-O-6-C-2' torsion populates only the gauche states, as deduced from J couplings. This is at variance with previous Langevin dynamics simulations in which the proportion of the trans state is significant. For the C-6-O-6-C-2'-H2' torsion an equal population of the three staggered conformers is compatible with experimental data, although previous simulations have indicated gauche conformers to be preferred. Since about half the number of the possible conformational states for the major degrees of freedom are significantly populated, as corroborated by experimental data, the flexibility of the substituting l-carboxyethyl group is large. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00240-7