2,5-ANHYDRO-3-DEOXY-3-(3,4-DIHYDRO-5-METHYL-2,4-DIOXO-1(2H)-PYRIMIDINYL)-D-IDITOL

Base Information

• Chemical Name: 2,5-ANHYDRO-3-DEOXY-3-(3,4-DIHYDRO-5-METHYL-2,4-DIOXO-1(2H)-PYRIMIDINYL)-D-IDITOL
• CAS No.: 302790-85-8
• Molecular Formula: C11H16N2O6
• Molecular Weight: 272.255
• Mol file: 302790-85-8.mol

Synonyms:2,5-ANHYDRO-3-DEOXY-3-(3,4-DIHYDRO-5-METHYL-2,4-DIOXO-1(2H)-PYRIMIDINYL)-D-IDITOL

Chemical Property of 2,5-ANHYDRO-3-DEOXY-3-(3,4-DIHYDRO-5-METHYL-2,4-DIOXO-1(2H)-PYRIMIDINYL)-D-IDITOL

Chemical Property:

• PSA: 0.00000
• LogP: 0.00000

Purity/Quality:

99%min ^*data from raw suppliers

2,5-ANHYDRO-3-DEOXY-3-(3,4-DIHYDRO-5-METHYL-2,4-DIOXO-1(2H)-PYRIMIDINYL)-D-IDITOL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,5-ANHYDRO-3-DEOXY-3-(3,4-DIHYDRO-5-METHYL-2,4-DIOXO-1(2H)-PYRIMIDINYL)-D-IDITOL

There total 14 articles about 2,5-ANHYDRO-3-DEOXY-3-(3,4-DIHYDRO-5-METHYL-2,4-DIOXO-1(2H)-PYRIMIDINYL)-D-IDITOL 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: 65.0%

2,5:3,4-dianhydro-1,6-di-O-benzoyl-D-altritol (91318-12-6) + thymin (65-71-4,28806-14-6,691841-57-3) → 3-deoxy-3-(thymin-1'-yl)-2,5-anhydro-D-mannitol (196596-88-0,302790-85-8,302790-81-4) + 4-deoxy-4-(thymin-1'-yl)-2,5-anhydro-D-iditol (196596-88-0,302790-85-8,302790-81-4)

Guidance literature:

2,5:3,4-dianhydro-1,6-di-O-benzoyl-D-altritol; thymin; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 90 ℃; for 24h;

With sodium methylate; In methanol; for 3h;

DOI:10.1016/S0957-4166(00)00246-9

Reference yield: 65.0%

2,5:3,4-dianhydro-1,6-di-O-benzoyl-D-altritol (91318-12-6) + thymin (65-71-4,28806-14-6,691841-57-3) → 3-deoxy-3-(thymin-1'-yl)-2,5-anhydro-D-mannitol (196596-88-0,302790-85-8,302790-81-4) + 4-deoxy-4-(thymin-1'-yl)-2,5-anhydro-D-iditol (196596-88-0,302790-85-8,302790-81-4)

Guidance literature:

2,5:3,4-dianhydro-1,6-di-O-benzoyl-D-altritol; thymin; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 90 ℃; for 24h;

With sodium methylate; In methanol; for 3h;

DOI:10.1016/S0957-4166(00)00246-9

Reference yield:

(+)-D-glucosamine hydrochloride (1078691-95-8) → 3-deoxy-3-(thymin-1'-yl)-2,5-anhydro-D-mannitol (196596-88-0,302790-85-8,302790-81-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: NaNO₂; conc. HCl / H₂O / 5 h / 0 °C

2.1: NaBH₄ / H₂O / 24 h / 20 °C

3.1: pyridine / CH₂Cl₂ / 6 h / 0 °C

4.1: 90 percent / PPh₃; diethyl azodicarboxylate / dioxane / 2 h / 70 °C

5.1: DBU / dimethylformamide / 24 h / 90 °C

5.2: 65 percent / NaOMe / methanol / 3 h

With pyridine; hydrogenchloride; sodium tetrahydroborate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; sodium nitrite; diethylazodicarboxylate; In 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; 1.1: Deamination / 2.1: Reduction / 3.1: Acylation / 4.1: intramolecular Mitsunobu reaction / 5.1: Ring cleavage / 5.2: methanolysis;

DOI:10.1016/S0957-4166(00)00246-9

upstream raw materials:

2,5-anhdyro-4-deoxy-4-(thymin-1-yl)-L-mannofuranose dimethyl acetal

thymin

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

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

Refernces

• 1、 Yang,Yu,Min,Ma,Zhang. "Stereoselective synthesis of 4-deoxy-4-nucleobase-2,5-anhydro-L-mannitol derivatives". . p. 2739 - 2747. Retrieved 2007/10/03.