1,3:4,6-di-O-benzylidene-2,5-di-O-benzyl-D-Mannitol | 99096-86-3

• 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: 1,3:4,6-di-O-benzylidene-2,5-di-O-benzyl-D-Mannitol
• 英文别名: 2,5-Di-o-benzyl-1,3:4,6-di-o-benzylidene-d-mannitol；(4R,5R)-2-phenyl-5-phenylmethoxy-4-[(4R,5R)-2-phenyl-5-phenylmethoxy-1,3-dioxan-4-yl]-1,3-dioxane
• CAS: 99096-86-3
• 化学式: C₃₄H₃₄O₆
• 分子量: 538.64
• InChiKey: FXHLPZKQASQZRV-VPXXDUEASA-N

物化性质

• 沸点：
  666.4±55.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  1,3:4,6-di-O-benzylidene-2,5-di-O-benzyl-D-Mannitol 在 盐酸 、 sodium periodate 、 硫酸 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 90.0h， 生成 2-O-benzyl-D-glyceraldehyde dimethylacetal
  参考文献：
  名称：

  New optically pure dimethylacetals of glyceraldehydes and their application for lipid and phospholipid synthesis

  摘要：

  A convenient synthesis of new and enantiomerically pure 2-O-protected D-glyceraldehyde dimethylacetals as chiral C-3 building blocks for the synthesis of lipids and phospholipids is described. Benzyl- or allylethers are used as protecting groups in position 2 and 5 of D-mannitol. These intermediates are converted to 2-O-benzyl- or 2-O-allyl-D-glyceraldehyde dimethylacetals by cleavage with periodic acid in methanol. The two dimethylacetals are useful for the synthesis of mixed chain phospholipids with natural configuration of ester-ester, ester-ether or ether-ether composition. Also, triglycerides with three different alkyl chains, ester or ether, can be prepared. As an example of the versatility of the new intermediates, we describe the synthesis of 1-O-hexahecyl-2-O-acetyl-sn-glycero-3-phosphocholine, the so-called 'platelet activating factor' (PAF), via 1-O-hexadecyl-2-O-benzyl-sn-glycerol.

  DOI：

  10.1016/0009-3084(95)02445-o
• 作为产物：
  描述：

  甘露醇 、 alkaline earth salt of/the/ methylsulfuric acid 在 硫酸 、 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 76.0h， 生成 1,3:4,6-di-O-benzylidene-2,5-di-O-benzyl-D-Mannitol
  参考文献：
  名称：

  New optically pure dimethylacetals of glyceraldehydes and their application for lipid and phospholipid synthesis

  摘要：

  A convenient synthesis of new and enantiomerically pure 2-O-protected D-glyceraldehyde dimethylacetals as chiral C-3 building blocks for the synthesis of lipids and phospholipids is described. Benzyl- or allylethers are used as protecting groups in position 2 and 5 of D-mannitol. These intermediates are converted to 2-O-benzyl- or 2-O-allyl-D-glyceraldehyde dimethylacetals by cleavage with periodic acid in methanol. The two dimethylacetals are useful for the synthesis of mixed chain phospholipids with natural configuration of ester-ester, ester-ether or ether-ether composition. Also, triglycerides with three different alkyl chains, ester or ether, can be prepared. As an example of the versatility of the new intermediates, we describe the synthesis of 1-O-hexahecyl-2-O-acetyl-sn-glycero-3-phosphocholine, the so-called 'platelet activating factor' (PAF), via 1-O-hexadecyl-2-O-benzyl-sn-glycerol.

  DOI：

  10.1016/0009-3084(95)02445-o

文献信息

• Highly selective silver(I) oxide mediated monoprotection of symmetrical diols
  作者：Abderrahim Bouzide、Gilles Sauvé

  DOI：10.1016/s0040-4039(97)01328-2

  日期：1997.8

  Treatment of symmetrical diol with Ag2O and alkyl halide gave the monoprotected derivative in good to excellent yield.

  用Ag 2 O和烷基卤处理对称的二醇以良好至优异的产率得到单保护的衍生物。
• New 3-O-Lauroyl-2-O-Benzyl-Glycerol Sulfonate
  作者：Liang Han、Zheng-Ming Li、Jian-Rong Gao

  DOI：10.3184/030823407x240917

  日期：2007.9

  The hydroxy groups of D-mannitol were protected by the formation of acetals and benzylethers and then 2-O-benzyl-D-glyceraldehyde dimethylacetal was prepared after the deprotection and oxygenolysis of the protected D-mannitol. In the presence of DCC and DMAP, the lauroyl group was introduced at the primary hydroxyl group of the dimethylacetal and 3-O-lauroyl-2-O-benzyl-glycerol was obtained after the deprotection of the dimethylacetal with FeCl₃·6H₂O and then reduction with NaBH₄. A series of new 3-O-lauroyl-2-O-benzyl-glycerol sulfonates was synthesised by the coupling of different sulfonyl groups with the 3-O-lauroyl-2-O-benzyl- glycerol. The bioactivities of the title compounds were tested and some compounds exhibited fungicidal activity against the tested fungi.

  D-mannitol 的羟基通过形成乙缩醛和苄基醚而得到保护，然后在对受保护的 D-mannitol 进行脱保护和氧解后制备出 2-O-苄基-D-甘油醛二甲基缩醛。在 DCC 和 DMAP 的存在下，在二甲基缩醛的伯羟基上引入月桂酰基，然后用 FeCl3-6H2O 对二甲基缩醛进行脱保护，再用 NaBH4 还原，就得到了 3-O-月桂酰基-2-O-苄基甘油。通过不同磺酰基与 3-O-lauroyl-2-O-benzyl- glycerol 的偶联，合成了一系列新的 3-O-lauroyl-2-O-benzyl- 甘油磺酸盐。对标题化合物的生物活性进行了测试，其中一些化合物对测试的真菌具有杀菌活性。
• 1,3:4,6-Di-O-benzylidene-d-mannitol as a source for novel chiral intermediates through regioselective reductive cleavage
  作者：Appu Aravind、Sundarababu Baskaran

  DOI：10.1016/j.tetlet.2004.12.036

  日期：2005.1

  Synthetically useful chiral intermediates have been synthesized starting from 1,3:4.6-di-O-benzylidene-D-mannitol by yields. regioselective reductive cleavage using (BF3Et2O)-Et-. and Et3SiH in high (C) 2004 Elsevier Ltd. All rights reserved.
• Stable liposomes with aqueous-soluble medicaments and methods for their preparation
  申请人：SYNTEX (U.S.A.) INC.

  公开号：EP0172007B1

  公开（公告）日：1991-05-22
• Chelation- and non-chelation-controlled additions to 2-O-benzyl-3-O-(tert-butyldimethylsilyl)glyceraldehyde
  作者：Manfred T. Reetz、Kurt Kesseler

  DOI：10.1021/jo00225a103

  日期：1985.12