1,1-anhydro-1-C-<2-(hydroxymethyl)phenyl>-2,3,4,6-tetra-O-benzyl-β-D-glucopyranose | 132814-52-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: 1,1-anhydro-1-C-<2-(hydroxymethyl)phenyl>-2,3,4,6-tetra-O-benzyl-β-D-glucopyranose
• 英文别名: (3S,3'R,4'S,5'R,6'R)-3',4',5'-tris(phenylmethoxy)-6'-(phenylmethoxymethyl)spiro[1H-2-benzofuran-3,2'-oxane]
• CAS: 132814-52-9
• 化学式: C₄₁H₄₀O₆
• 分子量: 628.765
• InChiKey: WMUCPLZEINPMPO-WEOXEBIHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  47
• 可旋转键数：
  13
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,1-anhydro-1-C-<2-(hydroxymethyl)phenyl>-2,3,4,6-tetra-O-benzyl-β-D-glucopyranose 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 5.0h， 以98%的产率得到1,1-anhydro-1-C-<2-(hydroxymethyl)phenyl>-β-D-glucopyranose
  参考文献：
  名称：

  C-Glycosides. 9. Stereospecific synthesis of C-glycosidic spiroketal of the papulacandins

  摘要：

  The reaction of ortho-lithiated triphenylmethyl benzyl ether with perbenzylated D-gluconolactone 1 followed by cyclization by BF3.Et2O provides a new stereospecific synthesis of C-glycosidic spiroketals. The structure of the peracetylated derivative was determined by X-ray diffraction. This methodology is applied to the synthesis of the spiroketal unit of papulacandins.

  DOI：

  10.1021/jo00022a014
• 作为产物：
  描述：

  5-内酯 在 三乙基硅烷 、 三氟化硼乙醚 、 氯化铵 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 1.0h， 生成 1,1-anhydro-1-C-<2-(hydroxymethyl)phenyl>-2,3,4,6-tetra-O-benzyl-β-D-glucopyranose
  参考文献：
  名称：

  C-Glycosides. 9. Stereospecific synthesis of C-glycosidic spiroketal of the papulacandins

  摘要：

  The reaction of ortho-lithiated triphenylmethyl benzyl ether with perbenzylated D-gluconolactone 1 followed by cyclization by BF3.Et2O provides a new stereospecific synthesis of C-glycosidic spiroketals. The structure of the peracetylated derivative was determined by X-ray diffraction. This methodology is applied to the synthesis of the spiroketal unit of papulacandins.

  DOI：

  10.1021/jo00022a014

文献信息

• SPIROKETAL DERIVATIVES AND USE THEREOF AS DIABETIC MEDICINE
  申请人：Kobayashi Takamitsu

  公开号：US20090030006A1

  公开（公告）日：2009-01-29

  The present invention provides a compound of Formula (I): wherein R 1 , R 2 , R 3 and R 4 are each independently selected from a hydrogen atom, an optionally substituted C 1 -C 6 alkyl group, an optionally substituted C 7 -C 14 aralkyl group and —C(═O)Rx; Rx represents an optionally substituted C 1 -C 6 alkyl group, an optionally substituted aryl group, an optionally substituted heteroaryl group, an optionally substituted C 1 -C 6 alkoxy group or —NReRf; Ar 1 represents an optionally substituted aromatic carbocyclic ring or an optionally mono-substituted aromatic heterocyclic ring; Q represents —(CH 2 ) m -(L) p - or -(L) p -(CH 2 ) m —; m represents an integer selected from 0 to 2, n represents an integer selected from 1 and 2, and p represents an integer selected from 0 and 1; L represents —O—, —S— or —NR 5 —; and A represents an optionally substituted aryl group or an optionally substituted heteroaryl group, a prodrug thereof and a pharmaceutically acceptable salt thereof, as well as a pharmaceutical preparation or pharmaceutical composition comprising such a compound.

  本发明提供了一种化合物，其化学式为(I)，其中R1、R2、R3和R4各自独立地选自氢原子、可选取代的C1-C6烷基、可选取代的C7-C14芳基烷基和—C(═O)Rx；Rx代表可选取代的C1-C6烷基、可选取代的芳基、可选取代的杂环芳基、可选取代的C1-C6烷氧基或—NReRf；Ar1代表可选取代的芳香环烷基或可选单取代的芳香杂环烷基；Q代表—(CH2)m-(L)p-或-(L)p-(CH2)m—；m代表选自0至2的整数，n代表选自1和2的整数，p代表选自0和1的整数；L代表—O—、—S—或—NR5—；A代表可选取代的芳基或可选取代的杂环芳基，以及该化合物的前药和药学上可接受的盐，以及包含该化合物的制药制备或制药组合物。
• US7767651B2
  申请人：——

  公开号：US7767651B2

  公开（公告）日：2010-08-03
• C-Glycosides. 9. Stereospecific synthesis of C-glycosidic spiroketal of the papulacandins
  作者：Stanislas Czernecki、Marie Claude Perlat

  DOI：10.1021/jo00022a014

  日期：1991.10

  The reaction of ortho-lithiated triphenylmethyl benzyl ether with perbenzylated D-gluconolactone 1 followed by cyclization by BF3.Et2O provides a new stereospecific synthesis of C-glycosidic spiroketals. The structure of the peracetylated derivative was determined by X-ray diffraction. This methodology is applied to the synthesis of the spiroketal unit of papulacandins.