2,5-Anhydro-4,6-di-Se-phenyl-4,6-diseleno-L-mannose Dimethyl Acetal

Base Information

• Chemical Name: 2,5-Anhydro-4,6-di-Se-phenyl-4,6-diseleno-L-mannose Dimethyl Acetal
• CAS No.: 67492-40-4
• Molecular Formula: C₂₀H₂₄O₄Se₂
• Molecular Weight: 486.328
• Mol file: 67492-40-4.mol

Synonyms:2,5-Anhydro-4,6-di-Se-phenyl-4,6-diseleno-L-mannose Dimethyl Acetal

Chemical Property of 2,5-Anhydro-4,6-di-Se-phenyl-4,6-diseleno-L-mannose Dimethyl Acetal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,5-Anhydro-4,6-di-Se-phenyl-4,6-diseleno-L-mannose Dimethyl Acetal

There total 7 articles about 2,5-Anhydro-4,6-di-Se-phenyl-4,6-diseleno-L-mannose Dimethyl Acetal which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

diphenyl diselenide (1666-13-3) + 2,5:3,4-dianhydro-L-talose dimethyl acetal p-toluenesulfonate (67492-43-7) → 2,5-Anhydro-4,6-di-Se-phenyl-4,6-diseleno-L-mannose Dimethyl Acetal (67492-40-4)

Guidance literature:

With sodium tetrahydroborate; In N,N-dimethyl-formamide; at 80 ℃;

DOI:10.1021/ja00545a018

Reference yield: 85.0%

3,6-di-O-p-tolylsulfonyl-2,5-anhydro-L-idofuranose dimethylacetal (39022-34-9) + diphenyl diselenide (1666-13-3) → 2,5-Anhydro-4,6-di-Se-phenyl-4,6-diseleno-L-mannose Dimethyl Acetal (67492-40-4)

Guidance literature:

With sodium tetrahydroborate; In N,N-dimethyl-formamide; at 80 ℃;

DOI:10.1021/ja00545a018

Reference yield:

3,6-di-O-p-tolylsulfonyl-2,5-anhydro-L-idofuranose dimethylacetal (39022-34-9) → 2,5-Anhydro-4,6-di-Se-phenyl-4,6-diseleno-L-mannose Dimethyl Acetal (67492-40-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / sodium hydride / tetrahydrofuran / 25 °C

2: dimethylformamide / Heating

With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/ja00522a095

upstream raw materials:

3,6-di-O-p-tolylsulfonyl-2,5-anhydro-L-idofuranose dimethylacetal

diphenyl diselenide

sodium phenylselenide

6-O-p-tolylsulfonyl-2,5:3,4-dianhydro-L-talofuranose dimethylacetal

Downstream raw materials:

N-[(R)-tert-Butylcarbamoyl-((2R,5S)-5-methyl-2,5-dihydro-furan-2-yl)-methyl]-benzamide

Toluene-4-sulfonic acid (2R,3R,5S)-2-dimethoxymethyl-5-methyl-tetrahydro-furan-3-yl ester

N-[(R)-tert-Butylcarbamoyl-((2R,5S)-5-methyl-2,5-dihydro-furan-2-yl)-methyl]-N-((R)-1-phenyl-ethyl)-benzamide

(αS,2R,5S)-N-tert-butyl-2,5-dihydro-5-methyl-α-benzamido>-2-furanacetamide

Refernces

• 1、 Wang, Pen-Chung,Joullie, Madeleine M.. "Synthesis of (2R,4S,5S)-Epiallomuscarine, (2S,3R,5S)-Isoepiallomuscarine, and (2S,3S,4S,5S)-3-Hydroxyepiallomuscarine from α-D-Glucose". . p. 5359 - 5363. Retrieved 2007/10/02.