(2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-[(2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-ol | 176169-16-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-[(2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-ol
• CAS: 176169-16-7
• 化学式: C₈₂H₈₈O₁₆
• 分子量: 1329.59
• InChiKey: MJWBHLDQKMIFGP-DMJZDQBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.1
• 重原子数：
  98.0
• 可旋转键数：
  35.0
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  158.68
• 氢给体数：
  1.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-[(2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-ol 、 2,3,6,2',3',4',6'-hepta-O-acetyl-α-D-maltosyl bromide 在 silver trifluoromethanesulfonate 、 1,1,3,3-四甲基脲 作用下， 以 二氯甲烷 为溶剂， 以89%的产率得到Methyl O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->4)-O-(2,3,5-tri-O-acetyl-β-D-glucopyranosyl)-(1->4)-O-(2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->4)-O-(2,3,6-tri-O-benzyl-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Synthetic α,β-(1→4)-Glucan Oligosaccharides as Models for Heparan Sulfate. Part II.

  摘要：

  alpha,beta-(1-->4)-Glucan oligosaccharides were prepared as models for heparan sulfate with the simplifying assumptions that carboxyl-reduction and sulfation of heparan sulfate does not decrease the SMC antiproliferative activity and that N-sulfates in glucosamines can be replaced by O-sulfates. The target saccharides were synthesized using maltosyl building blocks. Glycosylation of methyl 2,3,6-tri-O-benzyl-alpha-D-glucopyranoside (1) with hepta-O-acetyl-alpha-maltosyl bromide (2) furnished trisaccharide 3 which was deprotected to alpha-D-Glc-(1-->4)-beta-D-Glc-(1-->4)-alpha-D-Glc(1 --> OCH3) (5) or, alternatively, converted to the trisaccharide glycosyl acceptor (8) with one free hydroxyl function (4''-OH). Further silver triflate mediated glycosylation with glucosyl or maltosyl bromide followed by deblocking gave the tetrasaccharide beta-D-Glc-(1-->4)-alpha-D-Glc-(1-->4)-beta-D-Glc-(1-->4)-alpha-D-(1-->OCH3) (11) and the pentasaccharide [alpha-D-Glc-(1-->4)-beta-D-Glc-(1-->4)-alpha-D-Glc-(1-->OCH3) (14). The trisaccharides 3, 4, 6, and 8 as well as pentasaccharide 12 were fully characterized by H-1, 3, 8 and 12 also by C-13 NMR spectroscopy. Assignments were possible using 1D TOCSY, in some cases supplemented by 2D T-ROESY, H-1,H-1 2D COSY, and H-1-detected one-bond and multiple-bond H-1,C-13 2D COSY experiments.

  DOI：

  10.1080/07328309608005439
• 作为产物：
  描述：

  在 盐酸 、 3 A molecular sieve 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.0h， 以88%的产率得到(2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-[(2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-ol
  参考文献：
  名称：

  Synthetic α,β-(1→4)-Glucan Oligosaccharides as Models for Heparan Sulfate. Part II.

  摘要：

  alpha,beta-(1-->4)-Glucan oligosaccharides were prepared as models for heparan sulfate with the simplifying assumptions that carboxyl-reduction and sulfation of heparan sulfate does not decrease the SMC antiproliferative activity and that N-sulfates in glucosamines can be replaced by O-sulfates. The target saccharides were synthesized using maltosyl building blocks. Glycosylation of methyl 2,3,6-tri-O-benzyl-alpha-D-glucopyranoside (1) with hepta-O-acetyl-alpha-maltosyl bromide (2) furnished trisaccharide 3 which was deprotected to alpha-D-Glc-(1-->4)-beta-D-Glc-(1-->4)-alpha-D-Glc(1 --> OCH3) (5) or, alternatively, converted to the trisaccharide glycosyl acceptor (8) with one free hydroxyl function (4''-OH). Further silver triflate mediated glycosylation with glucosyl or maltosyl bromide followed by deblocking gave the tetrasaccharide beta-D-Glc-(1-->4)-alpha-D-Glc-(1-->4)-beta-D-Glc-(1-->4)-alpha-D-(1-->OCH3) (11) and the pentasaccharide [alpha-D-Glc-(1-->4)-beta-D-Glc-(1-->4)-alpha-D-Glc-(1-->OCH3) (14). The trisaccharides 3, 4, 6, and 8 as well as pentasaccharide 12 were fully characterized by H-1, 3, 8 and 12 also by C-13 NMR spectroscopy. Assignments were possible using 1D TOCSY, in some cases supplemented by 2D T-ROESY, H-1,H-1 2D COSY, and H-1-detected one-bond and multiple-bond H-1,C-13 2D COSY experiments.

  DOI：

  10.1080/07328309608005439