1,2-O-anhydro-3-O-benzyl-4,6-O-benzylidene-5a-carba-β-D-mannopyranose | 142789-96-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,2-O-anhydro-3-O-benzyl-4,6-O-benzylidene-5a-carba-β-D-mannopyranose
• 英文别名: 1,2-Anhydro-2-O-benzyl-4,6-O-benzylidene-5a-carba-β-D-mannopyranose；1,2-anhydro-3-O-benzyl-4,6-O-benzylidene-5a-carba-β-D-mannopyranose；(1R,3R,5R,6S,7R,9R)-9-phenyl-6-phenylmethoxy-4,8,10-trioxatricyclo[5.4.0.03,5]undecane
• CAS: 142789-96-6
• 化学式: C₂₁H₂₂O₄
• 分子量: 338.403
• InChiKey: TYLNKFFMJKONEV-OWQNAKTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2-O-anhydro-3-O-benzyl-4,6-O-benzylidene-5a-carba-β-D-mannopyranose 在 吡啶 、 tetrafluoroboric acid-diethyl ether complex 、 15-冠醚-5 、 乙酸酐 、 sodium hydride 、 溶剂黄146 、 二甲基亚砜 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 172.0h， 生成 dodecyl 2-O-acetyl-3-O-benzyl-4,6-di-O-methanesulfonyl-5a-carba-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of an ether-linked alkyl 5a-carba-β-d-glucoside, a 5a-carba-β-d-galactoside, a 2-acetamido-2-deoxy-5a-carba-β-d-glucoside, and an alkyl 5a′-carba-β-lactoside

  摘要：

  For the purpose of providing biologically stable building blocks for the biocombinatorial synthesis using a living cell, some ether-linked alkyl 5a-carba-beta-D-glycoside primers were prepared. The key step of the synthesis was coupling of 1-bromo-n-alkanes with the 1-OH unprotected derivatives of 5a-carba-sugar analogues of D-glucose, D-galactose, and 2-acetamido-2-deoxy-D-glucose (N-acetyl-D-glucosamine). in DMF in the presence of sodium hydride. Alternatively, alkyl carba-lactoside was synthesized by incorporation of a 5a-carba-beta-D-galactose residue into the 4-position of dodecyl beta-D-glueopyranoside, A strong and specific inhibition of beta-galactosidase (K-i 0.67 muM bovine liver) was found for dodecyl 5a-carba-beta-D-galactopyranoside. (C) 2002 Elsevier Science Ltd. All rights reserved,

  DOI：

  10.1016/s0008-6215(02)00294-x
• 作为产物：
  描述：

  (1R,3R,6R,10S)-10-hydroxy-3-phenyl-2,4-dioxabicyclo<4.4.0>dec-8-ene 在 sodium hypophosphite 、 sodium hydride 、 间氯过氧苯甲酸 、 sodium phosphate 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 1,2-O-anhydro-3-O-benzyl-4,6-O-benzylidene-5a-carba-β-D-mannopyranose
  参考文献：
  名称：

  Preparation of building blocks for carba-oligosaccharides related to cell-surface glycans

  摘要：

  DOI：

  10.1016/s0008-6215(00)90491-9

文献信息

• Synthesis of carbasugar-containing non-glycosidically linked pseudodisaccharides and higher pseudooligosaccharides
  作者：Ian Cumpstey

  DOI：10.1016/j.carres.2009.09.008

  日期：2009.11

  This minireview covers synthetic methods towards carbasugar-containing non-glycosidically linked pseudodisaccharides or higher pseudooligosaccharides. Carbocyclic pyranose mimetics (saturated or unsaturated between C-5 and C-5a) are linked by ether, thioether or amine bridges to carbohydrates or other carbasugars.

  这份简短的综述涵盖了针对含碳水化合物的非糖苷键连接的假二糖或高级假寡糖的合成方法。碳环吡喃糖模拟物（在C-5和C-5a之间饱和或不饱和）通过醚桥，硫醚桥或胺桥连接到碳水化合物或其他Carcarbugars。
• Synthesis of Building Blocks for Carba-oligosaccharides: 5a′-Carbamaltose and 5a′-Carbacellobiose, and 5a-Carba-β-d-mannopyranosyl-(1→4)-d-glucopyranose
  作者：Seiichiro Ogawa、Masahiro Ohmura、Seiichi Hisamatsu

  DOI：10.1055/s-2001-10800

  日期：——

  Practical synthesis of ether-linked 5a′-carbamaltose and -cellobiose, and the related carbadisaccharide starting from a sole condensate of the 1,2-anhydro-3-O-benzyl-4,6-O-benzylidene-5a-carba-β-d-mannopyranose and methyl 2,3,6-tri-O-benzyl-α-d-glucopyranoside is described.

  介绍了从 1,2-脱水-3-O-苄基-4,6-O-亚苄基-5a-carba-δ-d-吡喃甘露糖和甲基 2,3,6-三-O-苄基-δ-d-吡喃葡萄糖苷的唯一缩合物出发，合成醚键合 5a′-氨基麦芽糖和-cellobiose 以及相关碳二糖的实际方法。
• Tsunoda, Hidetoshi; Ogawa, Seiichiro, Liebigs Annalen der Chemie, 1994, # 2, p. 103 - 108
  作者：Tsunoda, Hidetoshi、Ogawa, Seiichiro

  DOI：——

  日期：——
• Preparation of Building Blocks for Carba‐Oligosaccharides: Some Protected 5a′‐Carba‐<scp>D</scp>‐hexopyranosyl‐1,5‐anhydro‐2‐deoxy‐<scp>D</scp>‐<i>arabino</i>‐hex‐1‐enitols, and 5a,5a′‐Dicarba Congeners Thereof
  作者：Seiichiro Ogawa、Yoshiyuki Senba

  DOI：10.1080/07328300600572907

  日期：2006.1.1

  Four configurational types of two protected O -linked (5a-carba-D-hexopyranosyl)-D-glucal and carba-D-glucal derivatives were prepared in order to provide versatile synthetic intermediates readily convertible into carba-oligosaccharides of biological interest. These compounds may also find application as donors for elongation of carba-oligosaccharide chains having O -linked carbahexopyranose residues at nonreducing ends.
• 10.1002/(sici)1099-0690(199806)1998:6<1099::aid-ejoc1099<3.0.co;2-r
  作者：Ogawa, Seiichiro、Hirai, Keisuke、Odagiri, Takashi、Matsunaga, Naoki、Yamazaki, Tetsuya、Nakajima, Akihiro

  DOI：10.1002/(sici)1099-0690(199806)1998:6<1099::aid-ejoc1099<3.0.co;2-r

  日期：——