(2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-iodomethyl-tetrahydro-pyran-2-ol | 131603-37-7

• 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)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-iodomethyl-tetrahydro-pyran-2-ol
• 英文别名: (2R,3R,4S,5R,6R)-2-(iodomethyl)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-ol
• CAS: 131603-37-7
• 化学式: C₃₅H₃₇IO₆
• 分子量: 680.58
• InChiKey: OIGNXYFTLKCNND-KJQSSVQNSA-N

物化性质

• 熔点：
  99 °C
• 沸点：
  724.8±60.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.48
• 重原子数：
  42.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  66.38
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-iodomethyl-tetrahydro-pyran-2-ol 在 三乙基硅烷 、 三氟化硼 、 三正丁基氢锡 、 L-Selectride 、 三乙胺 、 sodium nitrite 、 1,1'-偶氮(氰基环己烷) 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 生成 1,6-anhydro-3,4-dideoxy-4-C-(3,4,5,7-tetra-O-benzyl-2,6-anhydro-1-deoxy-α-D-gluco-2-heptulopyranos-1-yl)-D-glucopyranose
  参考文献：
  名称：

  C-Disaccharides I. Stereoselective approach to β-(1–4)-3-deoxy-C-disaccharides from levoglucosenone

  摘要：

  beta -(1-4)C-Disaccharides have been synthesized in four steps by stereoselective base catalyzed Michael addition reaction of glucosyl nitromethane to the chiral synthon, levoglucosenone followed by radical removal of the nitro group with tributyltinhydride. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00327-4
• 作为产物：
  描述：

  2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-hept-1-enitol 在 N-碘代丁二酰亚胺 作用下， 以 水 为溶剂， 生成 (2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-iodomethyl-tetrahydro-pyran-2-ol
  参考文献：
  名称：

  C-Disaccharides I. Stereoselective approach to β-(1–4)-3-deoxy-C-disaccharides from levoglucosenone

  摘要：

  beta -(1-4)C-Disaccharides have been synthesized in four steps by stereoselective base catalyzed Michael addition reaction of glucosyl nitromethane to the chiral synthon, levoglucosenone followed by radical removal of the nitro group with tributyltinhydride. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00327-4

文献信息

• Synthesis of N-aryl spiro-sulfamides as potential glycogen phosphorylase inhibitors
  作者：Tony Tite、Loic Tomas、Tibor Docsa、Pal Gergely、José Kovensky、David Gueyrard、Anne Wadouachi

  DOI：10.1016/j.tetlet.2011.12.049

  日期：2012.2

  A new C-glucosylated spiro-sulfamide has been prepared and evaluated toward glycogen phosphorylase inhibition. The synthesis was carried out successfully by nucleophilic displacement of 1-O-tosyl or 1-deoxy-1-iodo-alpha-D-gluco-hept-2-ulopyranose tetra-O-benzylated derivative using aryl amines. followed by the formation of the corresponding cyclic sulfamide. (C) 2011 Elsevier Ltd. All rights reserved.
• NOORT, DAAN;VEENEMAN, GERRIT H.;BOONS, GEERT-JAN P. H.;VAN, DER MAREL GIJ+, SYNLETT.,(1990) N, C. 205-206
  作者：NOORT, DAAN、VEENEMAN, GERRIT H.、BOONS, GEERT-JAN P. H.、VAN, DER MAREL GIJ+

  DOI：——

  日期：——