Methyl 5-amino-1,5-dideoxy-1-(3,4-dihydro-5-methyl-2,4-dioxo-1(2H)-pyrimidinyl)-β-D-allofuranuronate 2,3-diacetate

Base Information

• Chemical Name: Methyl 5-amino-1,5-dideoxy-1-(3,4-dihydro-5-methyl-2,4-dioxo-1(2H)-pyrimidinyl)-β-D-allofuranuronate 2,3-diacetate
• CAS No.: 127257-35-6
• Molecular Formula: C₁₆H₂₁N₃O₉
• Molecular Weight: 399.357
• Mol file: 127257-35-6.mol

Synonyms:Methyl 5-amino-1,5-dideoxy-1-(3,4-dihydro-5-methyl-2,4-dioxo-1(2H)-pyrimidinyl)-β-D-allofuranuronate 2,3-diacetate

Chemical Property of Methyl 5-amino-1,5-dideoxy-1-(3,4-dihydro-5-methyl-2,4-dioxo-1(2H)-pyrimidinyl)-β-D-allofuranuronate 2,3-diacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl 5-amino-1,5-dideoxy-1-(3,4-dihydro-5-methyl-2,4-dioxo-1(2H)-pyrimidinyl)-β-D-allofuranuronate 2,3-diacetate

There total 1 articles about Methyl 5-amino-1,5-dideoxy-1-(3,4-dihydro-5-methyl-2,4-dioxo-1(2H)-pyrimidinyl)-β-D-allofuranuronate 2,3-diacetate 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: 85.0%

1,2,3-Tri-O-acetyl-4-[(S)-Benzyloxycarbonylamino(methoxycarbonyl)methyl]-D-erythrofuranose (154799-95-8) + 2,4-bis(trimethylsiloxy)-5-methylpyrimidine (7288-28-0) → Methyl 5-amino-1,5-dideoxy-1-(3,4-dihydro-5-methyl-2,4-dioxo-1(2H)-pyrimidinyl)-β-D-allofuranuronate 2,3-diacetate (127257-35-6) + methyl 1,5-dideoxy-1-(3,4-dihydro-5-methyl-2,4-dioxo-1(2H)-pyrimidinyl)-5-[[(phenylmethoxy)carbonyl]amino]-β-D-allohexofuranuronate 2,3-diacetate (127257-34-5)

Guidance literature:

trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 100 ℃; for 0.5h;

DOI:10.1021/jo00299a017

Reference yield:

Methyl 5-amino-1,5-dideoxy-1-(3,4-dihydro-5-methyl-2,4-dioxo-1(2H)-pyrimidinyl)-β-D-allofuranuronate 2,3-diacetate (127257-35-6) → (S)-tert-Butoxycarbonylamino-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-acetic acid benzyl ester (155023-02-2)

Guidance literature:

Multi-step reaction with 3 steps

1: aq. Ba(OH)2 / dioxane / Ambient temperature

2: aq. K₂CO₃ / dioxane

3: NaHCO₃ / dimethylformamide / Ambient temperature

With barium dihydroxide; sodium hydrogencarbonate; potassium carbonate; In 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1039/c39940000111

Reference yield:

Methyl 5-amino-1,5-dideoxy-1-(3,4-dihydro-5-methyl-2,4-dioxo-1(2H)-pyrimidinyl)-β-D-allofuranuronate 2,3-diacetate (127257-35-6) → (S)-Amino-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-acetic acid benzyl ester; compound with trifluoro-acetic acid

Guidance literature:

Multi-step reaction with 4 steps

1: aq. Ba(OH)2 / dioxane / Ambient temperature

2: aq. K₂CO₃ / dioxane

3: NaHCO₃ / dimethylformamide / Ambient temperature

4: 100 percent / ethyl acetate / 0 °C

With barium dihydroxide; sodium hydrogencarbonate; potassium carbonate; In 1,4-dioxane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1039/c39940000111

upstream raw materials:

1,2,3-Tri-O-acetyl-4-[(S)-Benzyloxycarbonylamino(methoxycarbonyl)methyl]-D-erythrofuranose

2,4-bis(trimethylsiloxy)-5-methylpyrimidine

Downstream raw materials:

(S)-tert-Butoxycarbonylamino-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-acetic acid benzyl ester