(2R,3R,4R)-2-[(benzoyloxy)methyl]-3-(benzyloxy)-4-[[[(3-methoxy-1-oxo-2-(E)-propenyl)amino]carbonyl]amino]tetrahydrofuran

Base Information

• Chemical Name: (2R,3R,4R)-2-[(benzoyloxy)methyl]-3-(benzyloxy)-4-[[[(3-methoxy-1-oxo-2-(E)-propenyl)amino]carbonyl]amino]tetrahydrofuran
• CAS No.: 373647-01-9
• Molecular Formula: C₂₄H₂₆N₂O₇
• Molecular Weight: 454.48
• Mol file: 373647-01-9.mol

Synonyms:

Chemical Property of (2R,3R,4R)-2-[(benzoyloxy)methyl]-3-(benzyloxy)-4-[[[(3-methoxy-1-oxo-2-(E)-propenyl)amino]carbonyl]amino]tetrahydrofuran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R)-2-[(benzoyloxy)methyl]-3-(benzyloxy)-4-[[[(3-methoxy-1-oxo-2-(E)-propenyl)amino]carbonyl]amino]tetrahydrofuran

There total 10 articles about (2R,3R,4R)-2-[(benzoyloxy)methyl]-3-(benzyloxy)-4-[[[(3-methoxy-1-oxo-2-(E)-propenyl)amino]carbonyl]amino]tetrahydrofuran 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: 91.0%

silver cyanate (3315-16-0) + (2E)-3-methoxy-2-propenoyl chloride (6192-00-3,60778-73-6) + (2R,3R,4R)-4-amino-2-[(benzoyloxy)methyl]-3-(benzyloxy)tetrahydrofuran (373646-99-2) → (2R,3R,4R)-2-[(benzoyloxy)methyl]-3-(benzyloxy)-4-[[[(3-methoxy-1-oxo-2-(E)-propenyl)amino]carbonyl]amino]tetrahydrofuran (373647-01-9)

Guidance literature:

silver cyanate; (2E)-3-methoxy-2-propenoyl chloride; In toluene; for 0.5h; Heating;

(2R,3R,4R)-4-amino-2-[(benzoyloxy)methyl]-3-(benzyloxy)tetrahydrofuran; In N,N-dimethyl-formamide; toluene; at 20 ℃; for 24h;

DOI:10.1016/S0957-4166(01)00283-X

Reference yield:

(2S,3R,4R)-3-benzyloxy-2-iodomethyltetrahydrofuran-4-ol (334784-71-3) → (2R,3R,4R)-2-[(benzoyloxy)methyl]-3-(benzyloxy)-4-[[[(3-methoxy-1-oxo-2-(E)-propenyl)amino]carbonyl]amino]tetrahydrofuran (373647-01-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 96 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 3 h / 20 °C

2.1: pyridine / CH₂Cl₂ / 0.5 h / 20 °C

3.1: KNO₂; 18-crown-6 / dimethylformamide / 1 h / 20 °C

3.2: 61 mg / H₂O

4.1: 83 percent / pyridine / 72 h / 4 °C

5.1: 89 percent / NaN₃; 15-crown-5 / dimethylsulfoxide / 100 °C

6.1: Ph₃P / tetrahydrofuran / 2.5 h / 20 °C

6.2: 91 percent / H₂O / tetrahydrofuran / 1 h / Heating

7.1: toluene / 0.5 h / Heating

7.2: 91 percent / dimethylformamide; toluene / 24 h / 20 °C

With pyridine; sodium azide; potassium nitrite; 15-crown-5; 18-crown-6 ether; pyridinium p-toluenesulfonate; triphenylphosphine; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0957-4166(01)00283-X

Reference yield:

(2S,3S,4R)-3-benzyloxy-4-((1R/S)-(1-ethoxy)-ethoxy)-2-(iodomethyl)tetrahydrofuran (373646-85-6) → (2R,3R,4R)-2-[(benzoyloxy)methyl]-3-(benzyloxy)-4-[[[(3-methoxy-1-oxo-2-(E)-propenyl)amino]carbonyl]amino]tetrahydrofuran (373647-01-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: pyridine / CH₂Cl₂ / 0.5 h / 20 °C

2.1: KNO₂; 18-crown-6 / dimethylformamide / 1 h / 20 °C

2.2: 61 mg / H₂O

3.1: 83 percent / pyridine / 72 h / 4 °C

4.1: 89 percent / NaN₃; 15-crown-5 / dimethylsulfoxide / 100 °C

5.1: Ph₃P / tetrahydrofuran / 2.5 h / 20 °C

5.2: 91 percent / H₂O / tetrahydrofuran / 1 h / Heating

6.1: toluene / 0.5 h / Heating

6.2: 91 percent / dimethylformamide; toluene / 24 h / 20 °C

With pyridine; sodium azide; potassium nitrite; 15-crown-5; 18-crown-6 ether; triphenylphosphine; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0957-4166(01)00283-X

upstream raw materials:

silver cyanate

(2E)-3-methoxy-2-propenoyl chloride

(2R,3R,4R)-4-amino-2-[(benzoyloxy)methyl]-3-(benzyloxy)tetrahydrofuran

benzoyl chloride

Downstream raw materials:

1-[(3R,4R,5R)-4-(benzyloxy)-5-(hydroxymethyl)tetrahydrofuran-3-yl]uracil