methyl (2S,4R)-5-benzyloxycarbonylamino-2-tert-butoxycarbonylamino-4-hydroxypentanoate

Base Information

• Chemical Name: methyl (2S,4R)-5-benzyloxycarbonylamino-2-tert-butoxycarbonylamino-4-hydroxypentanoate
• CAS No.: 911225-68-8
• Molecular Formula: C₁₉H₂₈N₂O₇
• Molecular Weight: 396.441
• Mol file: 911225-68-8.mol

Synonyms:methyl (2S,4R)-5-benzyloxycarbonylamino-2-tert-butoxycarbonylamino-4-hydroxypentanoate

Chemical Property of methyl (2S,4R)-5-benzyloxycarbonylamino-2-tert-butoxycarbonylamino-4-hydroxypentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2S,4R)-5-benzyloxycarbonylamino-2-tert-butoxycarbonylamino-4-hydroxypentanoate

There total 16 articles about methyl (2S,4R)-5-benzyloxycarbonylamino-2-tert-butoxycarbonylamino-4-hydroxypentanoate 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:

((3S,5R)-5-Aminomethyl-2-oxo-tetrahydro-furan-3-yl)-carbamic acid tert-butyl ester → methyl (2S,4R)-5-benzyloxycarbonylamino-2-tert-butoxycarbonylamino-4-hydroxypentanoate (911225-68-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 0.079 g / NaHCO₃ / H₂O; dioxane; toluene / 12 h / 20 °C

2: sodium hydroxide / tetrahydrofuran / 0.5 h / 0 °C

3: 0.073 g / diethyl ether

With sodium hydroxide; sodium hydrogencarbonate; In tetrahydrofuran; 1,4-dioxane; diethyl ether; water; toluene;

DOI:10.1016/j.tet.2006.06.105

Reference yield:

(2S,4R)-2-tert-butoxycarbonylamino-4-iodomethyl-4-butanolide (911225-69-9) → methyl (2S,4R)-5-benzyloxycarbonylamino-2-tert-butoxycarbonylamino-4-hydroxypentanoate (911225-68-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 99 percent / NaN₃ / dimethylformamide / 12 h / 20 °C

2.1: triphenylphosphine / tetrahydrofuran / 5 h / 20 °C

2.2: tetrahydrofuran; H₂O / 5 h / 60 °C

3.1: 0.079 g / NaHCO₃ / H₂O; dioxane; toluene / 12 h / 20 °C

4.1: sodium hydroxide / tetrahydrofuran / 0.5 h / 0 °C

5.1: 0.073 g / diethyl ether

With sodium hydroxide; sodium azide; sodium hydrogencarbonate; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; diethyl ether; water; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.tet.2006.06.105

Reference yield:

(2S,4R)-2-azido-4-[(tert-butyldiphenylsilyloxy)methyl]-4-butanolide (911225-54-2) → methyl (2S,4R)-5-benzyloxycarbonylamino-2-tert-butoxycarbonylamino-4-hydroxypentanoate (911225-68-8)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 97 percent / triphenylphosphine / tetrahydrofuran / 0.5 h / 20 °C

2.1: 90 percent / triethylamine / dioxane / 12 h / 20 °C

3.1: 83 percent / HF*pyridine complex; pyridine / tetrahydrofuran / 48 h / 20 °C

4.1: 94 percent / triphenylphosphine; imidazole; I₂ / benzene / 12 h / 20 °C

5.1: 99 percent / NaN₃ / dimethylformamide / 12 h / 20 °C

6.1: triphenylphosphine / tetrahydrofuran / 5 h / 20 °C

6.2: tetrahydrofuran; H₂O / 5 h / 60 °C

7.1: 0.079 g / NaHCO₃ / H₂O; dioxane; toluene / 12 h / 20 °C

8.1: sodium hydroxide / tetrahydrofuran / 0.5 h / 0 °C

9.1: 0.073 g / diethyl ether

With pyridine; 1H-imidazole; sodium hydroxide; sodium azide; iodine; sodium hydrogencarbonate; pyridine hydrogenfluoride; triethylamine; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; diethyl ether; water; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1016/j.tet.2006.06.105

upstream raw materials:

diazomethane

(2S,4R)-2-tert-butoxycarbonylamino-4-iodomethyl-4-butanolide

(2S,4R)-2-azido-4-[(tert-butyldiphenylsilyloxy)methyl]-4-butanolide

(2S,4R)-2-amino-4-[(tert-butyldiphenylsilyloxy)methyl]-4-butanolide

Downstream raw materials:

(R)-3-benzyloxycarbonyl-5-<(S)-2-(tert-butoxycarbonylamino)-2-(methoxycarbonyl)ethyl>-2,2-dimethyl-1,3-oxazolidine