2,5-ANHYDRO-4-DEOXY-4-(3,4-DIHYDRO-2,4-DIOXO-1(2H)-PYRIMIDINYL)-1-(DIMETHYL ACETAL)-L-MANNOSE

Base Information

• Chemical Name: 2,5-ANHYDRO-4-DEOXY-4-(3,4-DIHYDRO-2,4-DIOXO-1(2H)-PYRIMIDINYL)-1-(DIMETHYL ACETAL)-L-MANNOSE
• CAS No.: 196596-84-6
• Molecular Formula: C12H18N2O7
• Molecular Weight: 316.308
• Mol file: 196596-84-6.mol

Synonyms:2,5-ANHYDRO-4-DEOXY-4-(3,4-DIHYDRO-2,4-DIOXO-1(2H)-PYRIMIDINYL)-1-(DIMETHYL ACETAL)-L-MANNOSE

Chemical Property of 2,5-ANHYDRO-4-DEOXY-4-(3,4-DIHYDRO-2,4-DIOXO-1(2H)-PYRIMIDINYL)-1-(DIMETHYL ACETAL)-L-MANNOSE

Chemical Property:

• PSA: 123.01000
• LogP: -2.18280

Purity/Quality:

99% ^*data from raw suppliers

2,5-ANHYDRO-4-DEOXY-4-(3,4-DIHYDRO-2,4-DIOXO-1(2H)-PYRIMIDINYL)-1-(DIMETHYL ACETAL)-L-MANNOSE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2,5-ANHYDRO-4-DEOXY-4-(3,4-DIHYDRO-2,4-DIOXO-1(2H)-PYRIMIDINYL)-1-(DIMETHYL ACETAL)-L-MANNOSE

There total 2 articles about 2,5-ANHYDRO-4-DEOXY-4-(3,4-DIHYDRO-2,4-DIOXO-1(2H)-PYRIMIDINYL)-1-(DIMETHYL ACETAL)-L-MANNOSE 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: 35.3%

uracil (66-22-8,144104-68-7,18324-22-6,27072-01-1,2920-92-5,51953-19-6) + 2,5:3,4-dianhydro-L-talofuranose dimethylacetal (171877-92-2) → 4-deoxy-4-(uracil-1-yl)-2,5-anhydro-L-mannofuranose dimethylacetal (196596-84-6)

Guidance literature:

With 18-crown-6 ether; potassium carbonate; In N,N-dimethyl-formamide; a) RT, 0.5 h, b) 80 deg C, 28 h;

DOI:10.1016/S0957-4166(97)00314-5

Reference yield:

3-O-p-tolylsulfonyl-2,5-anhydro-L-idofuranose dimethylacetal (196596-83-5) → 4-deoxy-4-(uracil-1-yl)-2,5-anhydro-L-mannofuranose dimethylacetal (196596-84-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 92.6 percent / K₂CO₃, CH₃OH / 2.5 h / Ambient temperature

2: 35.3 percent / K₂CO₃, 18-crown-6 / dimethylformamide / a) RT, 0.5 h, b) 80 deg C, 28 h

With methanol; 18-crown-6 ether; potassium carbonate; In N,N-dimethyl-formamide;

DOI:10.1016/S0957-4166(97)00314-5

Reference yield: 62.0%

4-deoxy-4-(uracil-1-yl)-2,5-anhydro-L-mannofuranose dimethylacetal (196596-84-6) → 6'-deoxy-6'-azido-4'-deoxy-4'-(uracil-1-yl)-2,3':2',5'-dianhydro-L-altrofuranose dimethyl acetal (900513-68-0) + 6'-deoxy-6'-azido-4'-deoxy-4'-(uracil-1-yl)-2',5'-anhydro-L-mannofuranose dimethyl acetal

Guidance literature:

4-deoxy-4-(uracil-1-yl)-2,5-anhydro-L-mannofuranose dimethylacetal; With sodium azide; carbon tetrabromide; triphenylphosphine; In N,N-dimethyl-formamide; at 20 ℃; for 58h;

In methanol; N,N-dimethyl-formamide; for 1h;

DOI:10.1016/j.tetasy.2006.03.034

upstream raw materials:

uracil

2,5:3,4-dianhydro-L-talofuranose dimethylacetal

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

Downstream raw materials:

4-deoxy-4-(uracil-1-yl)-2,5-anhydro-L-mannitol

6'-deoxy-6'-azido-4'-deoxy-4'-(uracil-1-yl)-2,3':2',5'-dianhydro-L-altrofuranose dimethyl acetal