1-O-benzyl-2-[(tert-butyloxycarbonyl)amino]-3-[N₃-benzoyl(thymin-1-yl)]-L-propanol

Base Information

• Chemical Name: 1-O-benzyl-2-[(tert-butyloxycarbonyl)amino]-3-[N₃-benzoyl(thymin-1-yl)]-L-propanol
• CAS No.: 179472-12-9
• Molecular Formula: C₂₇H₃₁N₃O₆
• Molecular Weight: 493.56
• Mol file: 179472-12-9.mol

Synonyms:1-O-benzyl-2-[(tert-butyloxycarbonyl)amino]-3-[N₃-benzoyl(thymin-1-yl)]-L-propanol

Chemical Property of 1-O-benzyl-2-[(tert-butyloxycarbonyl)amino]-3-[N₃-benzoyl(thymin-1-yl)]-L-propanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-O-benzyl-2-[(tert-butyloxycarbonyl)amino]-3-[N₃-benzoyl(thymin-1-yl)]-L-propanol

There total 5 articles about 1-O-benzyl-2-[(tert-butyloxycarbonyl)amino]-3-[N₃-benzoyl(thymin-1-yl)]-L-propanol 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: 86.0%

N-(tert-butyloxycarbonyl)-O-benzyl-L-serinol (79069-15-1) + N-3-benzoylthymine (4330-20-5) → 1-O-benzyl-2-[(tert-butyloxycarbonyl)amino]-3-[N3-benzoyl(thymin-1-yl)]-L-propanol (179472-12-9)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20 ℃; for 24h;

DOI:10.1080/07328319908044847

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → 1-O-benzyl-2-[(tert-butyloxycarbonyl)amino]-3-[N3-benzoyl(thymin-1-yl)]-L-propanol (179472-12-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 93 percent / Et₃N / tetrahydrofuran; H₂O / 20 °C

2: TEA / tetrahydrofuran / 0.5 h / -20 °C

3: 4.7 g / NaBH₄ / tetrahydrofuran; H₂O / 2 h / 0 °C

4: 86 percent / Ph₃P; DEAD / tetrahydrofuran / 24 h / 20 °C

With sodium tetrahydroborate; TEA; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; water; 1: Esterification / 2: Esterification / 3: Reduction / 4: Alkylation;

DOI:10.1080/07328319908044847

Reference yield:

O-Benzyl-L-serine (4726-96-9,32520-12-0) → 1-O-benzyl-2-[(tert-butyloxycarbonyl)amino]-3-[N3-benzoyl(thymin-1-yl)]-L-propanol (179472-12-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 93 percent / Et₃N / tetrahydrofuran; H₂O / 20 °C

2: TEA / tetrahydrofuran / 0.5 h / -20 °C

3: 4.7 g / NaBH₄ / tetrahydrofuran; H₂O / 2 h / 0 °C

4: 86 percent / Ph₃P; DEAD / tetrahydrofuran / 24 h / 20 °C

With sodium tetrahydroborate; TEA; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; water; 1: Esterification / 2: Esterification / 3: Reduction / 4: Alkylation;

DOI:10.1080/07328319908044847

upstream raw materials:

N-(tert-butyloxycarbonyl)-O-benzyl-L-serinol

N-3-benzoylthymine

di-tert-butyl dicarbonate

O-Benzyl-L-serine

Downstream raw materials:

2-[(tert-butyloxycarbonyl)amino]-3-[N₃-benzoyl(thymin-1-yl)]-L-propan-1-ol

1-O-isobutyryl-2-[(β-hydroxyacetyl)amino]-3-[N3-benzoyl(thymin-1-yl)]-L-propanol

1-O-isobutyryl-2-[(tert-butyloxycarbonyl)amino]-3-[N₃-benzoyl(thymin-1-yl)]-L-propanol

2-[[β-(4,4'-dimethoxytrityl)-O-acetyl]amino]-3-(thymin-1-yl)-L-propanol