2,5-anhydro-3,4-di-O-benzyl-1,6-di-O-trityl-D-mannitol | 887904-15-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 2,5-anhydro-3,4-di-O-benzyl-1,6-di-O-trityl-D-mannitol
• 英文别名: (2R,3R,4R,5R)-3,4-bis(phenylmethoxy)-2,5-bis(trityloxymethyl)oxolane
• CAS: 887904-15-6
• 化学式: C₅₈H₅₂O₅
• 分子量: 829.048
• InChiKey: INKLWWGIANCOPW-FQFJSIKISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.9
• 重原子数：
  63
• 可旋转键数：
  18
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,5-anhydro-3,4-di-O-benzyl-1,6-di-O-trityl-D-mannitol 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 氢溴酸 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 0.17h， 生成 2,5-anhydro-3,4-di-O-benzyl-1,6-bis-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-D-mannitol
  参考文献：
  名称：

  Glycosidation of 2,5-anhydro-3,4-di-O-benzyl-d-mannitol with different glucopyranosyl donors. A comparative study

  摘要：

  2,5-Anhydro-3,4-di-O-benzyl-D-Mannitol was glycosylated using different donors such as tetra-O-acetyl-alpha-D-glucopyranosyl bromide in the presence of Hg(CN)(2), the corresponding beta-thiophenylglycoside in the presence of NIS and TfOH as well as the alpha- and beta-trichloroimidate with TMSOTf as promoter. The resulting mixtures were analyzed by HPLC and the following main components were isolated and characterized: 2,5-anhydro-3,4-di-O-benzyl-1-O-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-D-mannitol; 6-O-acetyl-2,5-anhydro-3,4-di-O-benzyl-1-O-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-D-mannitol; 2,5-anhydro-3,4-di-O-benzyl -1,6-bis-O-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-D-mannitol; 2,5-anhydro-3,4-di-O-benzyl-1-O-[-2-O-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-3,4,6-tri-O-acetyl-beta-D-glucopyranosyl]-6-0-(2,3,4.6-tetra-O-acetyl-beta-D-glucopyranosyl)-D-mannitol and 2,5-anhydro-3,4-di-O-benzyl-1,6-bis-O-(3,4,6-tri-O-acetyl-1,2-O-ethylidene-2'-yl-alpha-D-glucopyranosyl)-D-mannitol. The latter compound representing a bis-orthoester might be a common intermediate in all the investigated reactions, as its rearrangement and/or decomposition can yield all of the isolated compounds. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.01.028
• 作为产物：
  描述：

  氯化苄 、 (2R,3R,4R,5R)-3,4-dihydroxy-2,5-di(trityloxymethyl)tetrahydrofuran 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 2,5-anhydro-3,4-di-O-benzyl-1,6-di-O-trityl-D-mannitol
  参考文献：
  名称：

  Glycosidation of 2,5-anhydro-3,4-di-O-benzyl-d-mannitol with different glucopyranosyl donors. A comparative study

  摘要：

  2,5-Anhydro-3,4-di-O-benzyl-D-Mannitol was glycosylated using different donors such as tetra-O-acetyl-alpha-D-glucopyranosyl bromide in the presence of Hg(CN)(2), the corresponding beta-thiophenylglycoside in the presence of NIS and TfOH as well as the alpha- and beta-trichloroimidate with TMSOTf as promoter. The resulting mixtures were analyzed by HPLC and the following main components were isolated and characterized: 2,5-anhydro-3,4-di-O-benzyl-1-O-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-D-mannitol; 6-O-acetyl-2,5-anhydro-3,4-di-O-benzyl-1-O-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-D-mannitol; 2,5-anhydro-3,4-di-O-benzyl -1,6-bis-O-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-D-mannitol; 2,5-anhydro-3,4-di-O-benzyl-1-O-[-2-O-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-3,4,6-tri-O-acetyl-beta-D-glucopyranosyl]-6-0-(2,3,4.6-tetra-O-acetyl-beta-D-glucopyranosyl)-D-mannitol and 2,5-anhydro-3,4-di-O-benzyl-1,6-bis-O-(3,4,6-tri-O-acetyl-1,2-O-ethylidene-2'-yl-alpha-D-glucopyranosyl)-D-mannitol. The latter compound representing a bis-orthoester might be a common intermediate in all the investigated reactions, as its rearrangement and/or decomposition can yield all of the isolated compounds. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.01.028

文献信息

• Antidiabetic phosphates
  申请人：AMERICAN CYANAMID COMPANY

  公开号：EP0354323A2

  公开（公告）日：1990-02-14

  Phosphates are disclosed which stimulate the enzyme fructose-1,6-bisphosphatase and inhibit the en­zyme 6-phosphofructo-1-kinase, thereby lowering glucose levels in mammals. These phosphates may thus be used to treat hyperglycemia and/or diabetes. Processes for the synthesis of the phosphates are also disclosed.

  已公开的磷酸盐可刺激果糖-1,6-二磷酸酶，抑制 6-磷酸果糖-1-激酶，从而降低哺乳动物体内的葡萄糖水平。因此，这些磷酸盐可用于治疗高血糖和/或糖尿病。此外，还公开了这些磷酸盐的合成工艺。
• US4968790A
  申请人：——

  公开号：US4968790A

  公开（公告）日：1990-11-06
• Glycosidation of 2,5-anhydro-3,4-di-O-benzyl-d-mannitol with different glucopyranosyl donors. A comparative study
  作者：Anikó Tegdes、Gábor Medgyes、Sándor Boros、János Kuszmann

  DOI：10.1016/j.carres.2006.01.028

  日期：2006.5

  2,5-Anhydro-3,4-di-O-benzyl-D-Mannitol was glycosylated using different donors such as tetra-O-acetyl-alpha-D-glucopyranosyl bromide in the presence of Hg(CN)(2), the corresponding beta-thiophenylglycoside in the presence of NIS and TfOH as well as the alpha- and beta-trichloroimidate with TMSOTf as promoter. The resulting mixtures were analyzed by HPLC and the following main components were isolated and characterized: 2,5-anhydro-3,4-di-O-benzyl-1-O-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-D-mannitol; 6-O-acetyl-2,5-anhydro-3,4-di-O-benzyl-1-O-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-D-mannitol; 2,5-anhydro-3,4-di-O-benzyl -1,6-bis-O-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-D-mannitol; 2,5-anhydro-3,4-di-O-benzyl-1-O-[-2-O-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-3,4,6-tri-O-acetyl-beta-D-glucopyranosyl]-6-0-(2,3,4.6-tetra-O-acetyl-beta-D-glucopyranosyl)-D-mannitol and 2,5-anhydro-3,4-di-O-benzyl-1,6-bis-O-(3,4,6-tri-O-acetyl-1,2-O-ethylidene-2'-yl-alpha-D-glucopyranosyl)-D-mannitol. The latter compound representing a bis-orthoester might be a common intermediate in all the investigated reactions, as its rearrangement and/or decomposition can yield all of the isolated compounds. (c) 2006 Elsevier Ltd. All rights reserved.