2-(2-aminopropanoyl-methyl-amino)-2-[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]acetic acid

Base Information

• Chemical Name: 2-(2-aminopropanoyl-methyl-amino)-2-[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]acetic acid
• CAS No.: 93806-87-2
• Molecular Formula: C₁₄H₂₀N₄O₈
• Molecular Weight: 372.335
• Mol file: 93806-87-2.mol

Synonyms:

Chemical Property of 2-(2-aminopropanoyl-methyl-amino)-2-[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]acetic acid

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: 1.605g/cm³

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-(2-aminopropanoyl-methyl-amino)-2-[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]acetic acid

There total 5 articles about 2-(2-aminopropanoyl-methyl-amino)-2-[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]acetic acid 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:

(S)-[((S)-2-Benzyloxycarbonylamino-propionyl)-methyl-amino]-[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-acetic acid (93806-88-3) → 1-<5'-(L-alanylmethylamino)-5'-deoxy-β-D-allofuranosyluronic acid>uracil (93806-87-2)

Guidance literature:

With hydrogen; acetic acid; Pd-BaSO₄; In methanol; water; for 1h; Yield given;

DOI:10.1021/jm00381a012

Reference yield:

1-(5'-amino-5'-deoxy-α-D-allofuranuronosyl)uracil (24695-48-5) → 1-<5'-(L-alanylmethylamino)-5'-deoxy-β-D-allofuranosyluronic acid>uracil (93806-87-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 73 percent / aq. NaOH, NaBH₄

2: 82 percent / NaBH₃CN / methanol / 0.33 h

3: 60 percent / AcOH, H₂ / 5percent Pd/BaSO₄ / H₂O

4: Et₃N / dimethylformamide; H₂O / 48 h

5: AcOH, H₂ / Pd/BaSO₄ / methanol; H₂O / 1 h

With sodium hydroxide; sodium tetrahydroborate; hydrogen; sodium cyanoborohydride; acetic acid; triethylamine; Pd-BaSO₄; In methanol; water; N,N-dimethyl-formamide;

DOI:10.1021/jm00381a012

Reference yield:

1-<5'-(methylamino)-5'-deoxy-β-D-allofuranosyluronic acid>uracil (93806-86-1) → 1-<5'-(L-alanylmethylamino)-5'-deoxy-β-D-allofuranosyluronic acid>uracil (93806-87-2)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N / dimethylformamide; H₂O / 48 h

2: AcOH, H₂ / Pd/BaSO₄ / methanol; H₂O / 1 h

With hydrogen; acetic acid; triethylamine; Pd-BaSO₄; In methanol; water; N,N-dimethyl-formamide;

DOI:10.1021/jm00381a012

upstream raw materials:

(S)-[((S)-2-Benzyloxycarbonylamino-propionyl)-methyl-amino]-[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-acetic acid

1-(5'-amino-5'-deoxy-α-D-allofuranuronosyl)uracil

1-<5'-(methylamino)-5'-deoxy-β-D-allofuranosyluronic acid>uracil

1-<5'-(benzylamino)-5'-deoxy-β-D-allofuranosyluronic acid>uracil