2,3,4,6-Tetra-O-benzyl-1-C--α-D-glucopyranose | 140658-49-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-Tetra-O-benzyl-1-C--α-D-glucopyranose
• 英文别名: 1-bis(methylthio)methyl-2,3,4,6-tetra-O-benzyl-α-D-glucopyranose；(2R,3R,4S,5R,6R)-2-[bis(methylsulfanyl)methyl]-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-ol
• CAS: 140658-49-7
• 化学式: C₃₇H₄₂O₆S₂
• 分子量: 646.869
• InChiKey: YREBIGRUSFZWRX-DUSCDBLMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  45
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,3,4,6-Tetra-O-benzyl-1-C--α-D-glucopyranose 在 镍 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 22.0h， 生成 1-O-Acetyl-2,3,4,6-tetra-O-benzyl-1-C-methyl-α-D-glucopyranose
  参考文献：
  名称：

  Synthesis of a branched-chain inosose derivative, a versatile synthon of N-substituted valiolamine derivatives from D-glucose

  摘要：

  The synthesis of (1S)-(1(OH)-2,4/1,3)-2,3,4-tri-O-benzyl-1-C-[(benzyloxy)methyl]-5-oxo-1,2,3,4-cyclohexanetetrol (7), which is an important synthon for the synthesis of valiolamine (8) 2 and its N-substituted derivatives such as AO-128 (9)3 having strong alpha-D-glucosidase inhibitory activity, is described. This branched-chain inosose derivative 7 has been prepared from the D-glucono-1,5-lactone derivative 2 which is readily available from D-glucose (1). The key step in the synthesis involves the stereospecific intramolecular carbocyclic ring, closure of the 1-deoxy-2, 6-heptodiulose derivatives 5a and 5b obtained by the oxidation of 2,3,4,6-tetra-O-benzyl-1-C-[bis-(methylthio)methyl]-D-glucitol (4a) and 2,3,4,6-tetra-O-benzyl-1-C-(dichloromethyl)-D-glucitol (4b). The resulting branched-chain bis(methylthio)inosose derivative 6a and dichloroinosose derivative 6b have been converted to the desired branched-chain inosose derivative 7 by desulfurization of 6a and dechlorination of 6b.

  DOI：

  10.1021/jo00039a025
• 作为产物：
  描述：

  2,3,4,6-四苄基-D-吡喃葡萄糖 在 正丁基锂 、 乙酸酐 、 二甲基亚砜 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 生成 2,3,4,6-Tetra-O-benzyl-1-C--α-D-glucopyranose
  参考文献：
  名称：

  An efficient diastereoselective synthesis of β-1-formyl-2,3,4,6-tetra-O-benzyl-d-glucopyranoside

  摘要：

  A diastereoselective synthesis of beta-1-formyl-2,3,4,6-tetra-O-benzyl-D-glucopyranoside in four steps, using an umpolung Seebach reaction is described. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01477-6

文献信息

• Inosose derivatives, production and use thereof
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0260121B1

  公开（公告）日：1993-03-10
• US4898986A
  申请人：——

  公开号：US4898986A

  公开（公告）日：1990-02-06
• US5004838A
  申请人：——

  公开号：US5004838A

  公开（公告）日：1991-04-02
• Synthesis of a branched-chain inosose derivative, a versatile synthon of N-substituted valiolamine derivatives from D-glucose
  作者：Hiroshi Fukase、Satoshi Horii

  DOI：10.1021/jo00039a025

  日期：1992.6

  The synthesis of (1S)-(1(OH)-2,4/1,3)-2,3,4-tri-O-benzyl-1-C-[(benzyloxy)methyl]-5-oxo-1,2,3,4-cyclohexanetetrol (7), which is an important synthon for the synthesis of valiolamine (8) 2 and its N-substituted derivatives such as AO-128 (9)3 having strong alpha-D-glucosidase inhibitory activity, is described. This branched-chain inosose derivative 7 has been prepared from the D-glucono-1,5-lactone derivative 2 which is readily available from D-glucose (1). The key step in the synthesis involves the stereospecific intramolecular carbocyclic ring, closure of the 1-deoxy-2, 6-heptodiulose derivatives 5a and 5b obtained by the oxidation of 2,3,4,6-tetra-O-benzyl-1-C-[bis-(methylthio)methyl]-D-glucitol (4a) and 2,3,4,6-tetra-O-benzyl-1-C-(dichloromethyl)-D-glucitol (4b). The resulting branched-chain bis(methylthio)inosose derivative 6a and dichloroinosose derivative 6b have been converted to the desired branched-chain inosose derivative 7 by desulfurization of 6a and dechlorination of 6b.
• An efficient diastereoselective synthesis of β-1-formyl-2,3,4,6-tetra-O-benzyl-d-glucopyranoside
  作者：Frédéric Labéguère、Jean-Pierre Lavergne、Jean Martinez

  DOI：10.1016/s0040-4039(02)01477-6

  日期：2002.9

  A diastereoselective synthesis of beta-1-formyl-2,3,4,6-tetra-O-benzyl-D-glucopyranoside in four steps, using an umpolung Seebach reaction is described. (C) 2002 Elsevier Science Ltd. All rights reserved.