(S)-3-[(2R,3S,5R)-5-(3-Benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-(2-methoxy-acetoxy)-tetrahydro-furan-2-ylmethoxymethoxy]-2-benzyloxycarbonylamino-propionic acid benzyl ester

Base Information

• Chemical Name: (S)-3-[(2R,3S,5R)-5-(3-Benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-(2-methoxy-acetoxy)-tetrahydro-furan-2-ylmethoxymethoxy]-2-benzyloxycarbonylamino-propionic acid benzyl ester
• CAS No.: 133510-64-2
• Molecular Formula: C₃₉H₄₁N₃O₁₃
• Molecular Weight: 759.767
• Mol file: 133510-64-2.mol

Synonyms:(S)-3-[(2R,3S,5R)-5-(3-Benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-(2-methoxy-acetoxy)-tetrahydro-furan-2-ylmethoxymethoxy]-2-benzyloxycarbonylamino-propionic acid benzyl ester

Chemical Property of (S)-3-[(2R,3S,5R)-5-(3-Benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-(2-methoxy-acetoxy)-tetrahydro-furan-2-ylmethoxymethoxy]-2-benzyloxycarbonylamino-propionic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-[(2R,3S,5R)-5-(3-Benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-(2-methoxy-acetoxy)-tetrahydro-furan-2-ylmethoxymethoxy]-2-benzyloxycarbonylamino-propionic acid benzyl ester

There total 6 articles about (S)-3-[(2R,3S,5R)-5-(3-Benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-(2-methoxy-acetoxy)-tetrahydro-furan-2-ylmethoxymethoxy]-2-benzyloxycarbonylamino-propionic acid benzyl ester 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: 84.0%

N-benzyloxycarbonyl-L-serine benzyl ester (21209-51-8) + 5'-O-methylthiomethyl-3'-O-methoxyacetyl-N3-benzoyl-thymidine (133510-61-9) → (S)-3-[(2R,3S,5R)-5-(3-Benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-(2-methoxy-acetoxy)-tetrahydro-furan-2-ylmethoxymethoxy]-2-benzyloxycarbonylamino-propionic acid benzyl ester (133510-64-2)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; In diethyl ether; 1,2-dichloro-ethane; at 0 ℃; for 0.0166667h;

DOI:10.1016/S0040-4020(01)86429-2

Reference yield:

Methoxy-acetic acid (2R,3S,5R)-5-(3-benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yl ester (130867-58-2) → (S)-3-[(2R,3S,5R)-5-(3-Benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-(2-methoxy-acetoxy)-tetrahydro-furan-2-ylmethoxymethoxy]-2-benzyloxycarbonylamino-propionic acid benzyl ester (133510-64-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / 90percent aq. acetic acid / 0.5 h / 50 °C

2: 72 percent / benzoyl peroxide / acetonitrile / 2 h / Ambient temperature

3: 84 percent / N-iodosuccinimide (NIS) / TfOH / 1,2-dichloro-ethane; diethyl ether / 0.02 h / 0 °C

With N-iodo-succinimide; acetic acid; dibenzoyl peroxide; trifluorormethanesulfonic acid; In diethyl ether; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1016/S0040-4020(01)86429-2

Reference yield:

3'-O-methoxyacetyl-N3-benzoyl-thymidine (130867-61-7) → (S)-3-[(2R,3S,5R)-5-(3-Benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-(2-methoxy-acetoxy)-tetrahydro-furan-2-ylmethoxymethoxy]-2-benzyloxycarbonylamino-propionic acid benzyl ester (133510-64-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / benzoyl peroxide / acetonitrile / 2 h / Ambient temperature

2: 84 percent / N-iodosuccinimide (NIS) / TfOH / 1,2-dichloro-ethane; diethyl ether / 0.02 h / 0 °C

With N-iodo-succinimide; dibenzoyl peroxide; trifluorormethanesulfonic acid; In diethyl ether; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1016/S0040-4020(01)86429-2

upstream raw materials:

N-benzyloxycarbonyl-L-serine benzyl ester

5'-O-methylthiomethyl-3'-O-methoxyacetyl-N³-benzoyl-thymidine

3'-O-methoxyacetyl-N³-benzoyl-thymidine

5’-O-dimethoxytrityl-3’-O-methoxyacetylthymidine