(S)-2-tert-Butoxycarbonylamino-3-phenyl-propionic acid (2S,3R,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-3-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionyloxymethyl)-tetrahydro-furan-2-ylmethyl ester

Base Information

• Chemical Name: (S)-2-tert-Butoxycarbonylamino-3-phenyl-propionic acid (2S,3R,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-3-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionyloxymethyl)-tetrahydro-furan-2-ylmethyl ester
• CAS No.: 209610-79-7
• Molecular Formula: C₃₈H₄₉N₅O₁₀
• Molecular Weight: 735.835
• Mol file: 209610-79-7.mol

Synonyms:

Chemical Property of (S)-2-tert-Butoxycarbonylamino-3-phenyl-propionic acid (2S,3R,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-3-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionyloxymethyl)-tetrahydro-furan-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-tert-Butoxycarbonylamino-3-phenyl-propionic acid (2S,3R,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-3-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionyloxymethyl)-tetrahydro-furan-2-ylmethyl ester

There total 4 articles about (S)-2-tert-Butoxycarbonylamino-3-phenyl-propionic acid (2S,3R,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-3-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionyloxymethyl)-tetrahydro-furan-2-ylmethyl 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: 17.0%

(S)-2-tert-Butoxycarbonylamino-3-phenyl-propionic acid (2S,3R,5R)-3-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionyloxymethyl)-5-[4-(dimethylamino-methyleneamino)-2-oxo-2H-pyrimidin-1-yl]-tetrahydro-furan-2-ylmethyl ester → (S)-2-tert-Butoxycarbonylamino-3-phenyl-propionic acid (2S,3R,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-3-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionyloxymethyl)-tetrahydro-furan-2-ylmethyl ester (209610-79-7)

Guidance literature:

In methanol; water; at 60 ℃; for 16h;

DOI:10.1016/S0968-0896(98)00020-0

Reference yield:

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → (S)-2-tert-Butoxycarbonylamino-3-phenyl-propionic acid (2S,3R,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-3-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionyloxymethyl)-tetrahydro-furan-2-ylmethyl ester (209610-79-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / DMAP, DCC / ethyl acetate / 36 h / Ambient temperature

2: 17 percent / methanol; H₂O / 16 h / 60 °C

With dmap; dicyclohexyl-carbodiimide; In methanol; water; ethyl acetate;

DOI:10.1016/S0968-0896(98)00020-0

Reference yield:

2',3'-dideoxy-3'-C-hydroxymethyl-β-D-erythropentofuranosylcytosine (132235-73-5) → (S)-2-tert-Butoxycarbonylamino-3-phenyl-propionic acid (2S,3R,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-3-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionyloxymethyl)-tetrahydro-furan-2-ylmethyl ester (209610-79-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / dimethylformamide / 12 h / Ambient temperature

2: 86 percent / DMAP, DCC / ethyl acetate / 36 h / Ambient temperature

3: 17 percent / methanol; H₂O / 16 h / 60 °C

With dmap; dicyclohexyl-carbodiimide; In methanol; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(98)00020-0

upstream raw materials:

N-tert-butoxycarbonyl-L-phenylalanine

2',3'-dideoxy-3'-C-hydroxymethyl-β-D-erythropentofuranosylcytosine

N'-[1-((2R,4R,5S)-4,5-Bis-hydroxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-N,N-dimethyl-formamidine