4-Amino-1-((1R,3R,4R,5R)-4-benzyloxy-3-hydroxymethyl-2,6-dioxa-bicyclo[3.2.0]hept-1-yl)-1H-pyrimidin-2-one

Base Information

• Chemical Name: 4-Amino-1-((1R,3R,4R,5R)-4-benzyloxy-3-hydroxymethyl-2,6-dioxa-bicyclo[3.2.0]hept-1-yl)-1H-pyrimidin-2-one
• CAS No.: 864237-74-1
• Molecular Formula: C₁₇H₁₉N₃O₅
• Molecular Weight: 345.355
• Mol file: 864237-74-1.mol

Synonyms:4-Amino-1-((1R,3R,4R,5R)-4-benzyloxy-3-hydroxymethyl-2,6-dioxa-bicyclo[3.2.0]hept-1-yl)-1H-pyrimidin-2-one

Chemical Property of 4-Amino-1-((1R,3R,4R,5R)-4-benzyloxy-3-hydroxymethyl-2,6-dioxa-bicyclo[3.2.0]hept-1-yl)-1H-pyrimidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Amino-1-((1R,3R,4R,5R)-4-benzyloxy-3-hydroxymethyl-2,6-dioxa-bicyclo[3.2.0]hept-1-yl)-1H-pyrimidin-2-one

There total 6 articles about 4-Amino-1-((1R,3R,4R,5R)-4-benzyloxy-3-hydroxymethyl-2,6-dioxa-bicyclo[3.2.0]hept-1-yl)-1H-pyrimidin-2-one 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: 70.0%

Acetic acid (1R,3R,4R,5R)-4-benzyloxy-1-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,6-dioxa-bicyclo[3.2.0]hept-3-ylmethyl ester (864237-79-6) → 4-Amino-1-((1R,3R,4R,5R)-4-benzyloxy-3-hydroxymethyl-2,6-dioxa-bicyclo[3.2.0]hept-1-yl)-1H-pyrimidin-2-one (864237-74-1)

Guidance literature:

Acetic acid (1R,3R,4R,5R)-4-benzyloxy-1-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,6-dioxa-bicyclo[3.2.0]hept-3-ylmethyl ester; With tris(triazolyl)phosphate; In acetonitrile;

With ammonium hydroxide; In 1,4-dioxane; at 20 ℃; for 16h;

With ammonia; In methanol; at 20 ℃; for 6h;

DOI:10.1055/s-2005-871547

Reference yield:

1-((1R,3R,4R,5R)-4-Benzyloxy-3-hydroxymethyl-2,6-dioxa-bicyclo[3.2.0]hept-1-yl)-1H-pyrimidine-2,4-dione (864237-73-0) → 4-Amino-1-((1R,3R,4R,5R)-4-benzyloxy-3-hydroxymethyl-2,6-dioxa-bicyclo[3.2.0]hept-1-yl)-1H-pyrimidin-2-one (864237-74-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 96 percent / DMAP; pyridine / 0.5 h / 20 °C

2.1: tris(triazolyl)phosphate / acetonitrile

2.2: aq. ammonia / dioxane / 16 h / 20 °C

2.3: 70 percent / NH₃ / methanol / 6 h / 20 °C

With pyridine; dmap; tris(triazolyl)phosphate; In acetonitrile;

DOI:10.1055/s-2005-871547

Reference yield:

Methanesulfonic acid (2R,3S,4R,5R)-4-benzyloxy-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,5-bis-hydroxymethyl-tetrahydro-furan-3-yl ester (864237-72-9) → 4-Amino-1-((1R,3R,4R,5R)-4-benzyloxy-3-hydroxymethyl-2,6-dioxa-bicyclo[3.2.0]hept-1-yl)-1H-pyrimidin-2-one (864237-74-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 46 percent / MeONa / methanol / 5 h / Heating

2.1: 96 percent / DMAP; pyridine / 0.5 h / 20 °C

3.1: tris(triazolyl)phosphate / acetonitrile

3.2: aq. ammonia / dioxane / 16 h / 20 °C

3.3: 70 percent / NH₃ / methanol / 6 h / 20 °C

With pyridine; dmap; tris(triazolyl)phosphate; sodium methylate; In methanol; acetonitrile;

DOI:10.1055/s-2005-871547

upstream raw materials:

Acetic acid (1R,3R,4R,5R)-4-benzyloxy-1-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,6-dioxa-bicyclo[3.2.0]hept-3-ylmethyl ester

1-((1R,3R,4R,5R)-4-Benzyloxy-3-hydroxymethyl-2,6-dioxa-bicyclo[3.2.0]hept-1-yl)-1H-pyrimidine-2,4-dione

Methanesulfonic acid (2R,3S,4R,5R)-4-benzyloxy-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,5-bis-hydroxymethyl-tetrahydro-furan-3-yl ester

(2R,3R,3aS,9aR)-3-Benzyloxy-2,9a-bis-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-2,3,3a,9a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one