benzyl 2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranoside | 215794-96-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranoside
• CAS: 215794-96-0
• 化学式: C₂₉H₃₂O₆
• 分子量: 476.569
• InChiKey: YVZIMPYFNYVOKF-JAIMTWQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.05
• 重原子数：
  35.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  benzyl 2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以94.8%的产率得到benzyl 3,4-di-O-benzyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis of the α-d-GlcpA-(1→3)-α-l-Rhap-(1→2)-l-Rha trisaccharide isolated from the cell wall hydrolyzate of the green alga, Chlorella vulgaris

  摘要：

  The title trisaccharide was synthesized from 6-O-acetyl-2,3,4-tri-O-benzyl-alpha -D-glucopyranosyl chloride (10), ethyl 2,4-di-O-benzyl-1-thio- (5) and benzyl 3,4-di-O-benzyl-alpha -L-rhamnopyranoside (9). The disaccharide 11 obtained from compounds 5 and 10 was used as the glycosyl donor to glycosylate the rhamnopyranoside derivative 9 having free OH-2 using the NIS-AgOTf-mediated glycosylation methodology. Zemplen deacetylation of the trisaccharide 12 resulted in the 6 " -OH derivative (13), which was selectively oxidized with CrO3 to the uronic acid derivative 14. The benzyl groups were removed by catalytic hydrogenolysis to furnish the target trisaccharide (1). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00196-3
• 作为产物：
  描述：

  ethyl 2,3-O-benzylidene-1-thio-α-L-rhamnopyranoside 在 吡啶 、 lithium aluminium tetrahydride 、 三氯化铝 、 molecular sieve 、 sodium hydride 、 三氟甲烷磺酸甲酯 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.25h， 生成 benzyl 2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis of the α-d-GlcpA-(1→3)-α-l-Rhap-(1→2)-l-Rha trisaccharide isolated from the cell wall hydrolyzate of the green alga, Chlorella vulgaris

  摘要：

  The title trisaccharide was synthesized from 6-O-acetyl-2,3,4-tri-O-benzyl-alpha -D-glucopyranosyl chloride (10), ethyl 2,4-di-O-benzyl-1-thio- (5) and benzyl 3,4-di-O-benzyl-alpha -L-rhamnopyranoside (9). The disaccharide 11 obtained from compounds 5 and 10 was used as the glycosyl donor to glycosylate the rhamnopyranoside derivative 9 having free OH-2 using the NIS-AgOTf-mediated glycosylation methodology. Zemplen deacetylation of the trisaccharide 12 resulted in the 6 " -OH derivative (13), which was selectively oxidized with CrO3 to the uronic acid derivative 14. The benzyl groups were removed by catalytic hydrogenolysis to furnish the target trisaccharide (1). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00196-3

文献信息

• Synthesis and glycosylation of pyrimidin-2-yl 1-thio-α-d-manno- and -α-l-rhamnopyranoside
  作者：Xianglan Ding、Guangbin Yang、Fanzuo Kong

  DOI：10.1016/s0008-6215(98)00164-5

  日期：1998.8

  Pyrimidin-2-yl 2,3,4,6-tetra-O-benzyl-1-thio-alpha-D-mannopyrano side (9), pyrimidin-2-yl 2,3,4-tri-O-benzyl-alpha-L-rhamnopyranoside (10), pyrimidin-2-yl 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-alpha-D-mannopyranoside (7), and pyrimidin-2-y1 2-O-acetyl-3,4-di-O-benzyl-1-thio-alpha-L-rhamnopyranoside (8) were prepared almost quantitatively fi om the corresponding protected 1,2-O-methoxyethylidene-beta-D-manno-or-beta-L-rhamnopyranose with 2-mercaptopyrimidine in the presence of mercuric bromide. Coupling reactions of the thioglycosides promoted by silver triflate with suitable glycosyl accepters afforded 1,2-trans linked disaccharides. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.