(2R,4S)-2-tert-butyldimethylsiloxymethyl-4-[(S)-O-tertbutyldiphenylsiloxymethyl-N-(6-N-fluorenylmethoxycarbonyl)serylamino]-6-methyl-1,2-oxiranylheptane

Base Information

• Chemical Name: (2R,4S)-2-tert-butyldimethylsiloxymethyl-4-[(S)-O-tertbutyldiphenylsiloxymethyl-N-(6-N-fluorenylmethoxycarbonyl)serylamino]-6-methyl-1,2-oxiranylheptane
• CAS No.: 214753-63-6
• Molecular Formula: C₅₅H₇₅N₃O₈Si₂
• Molecular Weight: 962.387
• Mol file: 214753-63-6.mol

Synonyms:(2R,4S)-2-tert-butyldimethylsiloxymethyl-4-[(S)-O-tertbutyldiphenylsiloxymethyl-N-(6-N-fluorenylmethoxycarbonyl)serylamino]-6-methyl-1,2-oxiranylheptane

Chemical Property of (2R,4S)-2-tert-butyldimethylsiloxymethyl-4-[(S)-O-tertbutyldiphenylsiloxymethyl-N-(6-N-fluorenylmethoxycarbonyl)serylamino]-6-methyl-1,2-oxiranylheptane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4S)-2-tert-butyldimethylsiloxymethyl-4-[(S)-O-tertbutyldiphenylsiloxymethyl-N-(6-N-fluorenylmethoxycarbonyl)serylamino]-6-methyl-1,2-oxiranylheptane

There total 10 articles about (2R,4S)-2-tert-butyldimethylsiloxymethyl-4-[(S)-O-tertbutyldiphenylsiloxymethyl-N-(6-N-fluorenylmethoxycarbonyl)serylamino]-6-methyl-1,2-oxiranylheptane 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: 75.0%

(2S,4S)-4-amino-2-tert-butyldimethylsiloxymethyl-3-oxo-6-methyl-1,2-oxiranylheptane (214753-31-8) + (S)-[O-tertbutyldiphenylsiloxymethyl-N-(6-N-fluorenylmethoxycarbonylamino)hexanoyl]serine (214753-58-9) → (2R,4S)-2-tert-butyldimethylsiloxymethyl-4-[(S)-O-tertbutyldiphenylsiloxymethyl-N-(6-N-fluorenylmethoxycarbonyl)serylamino]-6-methyl-1,2-oxiranylheptane (214753-63-6)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In dichloromethane; at 20 ℃; for 8h;

DOI:10.1016/S0968-0896(98)00089-3

Reference yield:

N-carbobenzoxy-L-leucinal (70853-26-8,86852-22-4,71413-15-5) → (2R,4S)-2-tert-butyldimethylsiloxymethyl-4-[(S)-O-tertbutyldiphenylsiloxymethyl-N-(6-N-fluorenylmethoxycarbonyl)serylamino]-6-methyl-1,2-oxiranylheptane (214753-63-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: t-BuLi / diethyl ether / 4 h / -78 - 0 °C

1.2: 54 percent / diethyl ether / 3.5 h / -78 - 0 °C

2.1: 80 percent / imidazole / tetrahydrofuran / 12 h / 20 °C

3.1: 93 percent / (ClCO)2; Et₃N; DMSO / CH₂Cl₂ / -78 - 20 °C

4.1: H₂O₂; i-Pr₂NEt / benzonitrile / 15 h / 0 - 4 °C

5.1: 97 percent / H₂ / Pd-c / methanol

6.1: 75 percent / i-Pr₂NEt; HATU / CH₂Cl₂ / 8 h / 20 °C

With 1H-imidazole; oxalyl dichloride; hydrogen; dihydrogen peroxide; tert.-butyl lithium; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; benzonitrile; 1.1: Metallation / 1.2: Addition / 2.1: Substitution / 3.1: Swern oxidation / 4.1: Epoxidation / 5.1: Hydrogenolysis / 6.1: Substitution;

DOI:10.1016/S0968-0896(98)00089-3

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (2R,4S)-2-tert-butyldimethylsiloxymethyl-4-[(S)-O-tertbutyldiphenylsiloxymethyl-N-(6-N-fluorenylmethoxycarbonyl)serylamino]-6-methyl-1,2-oxiranylheptane (214753-63-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 80 percent / imidazole / tetrahydrofuran / 12 h / 20 °C

2: 93 percent / (ClCO)2; Et₃N; DMSO / CH₂Cl₂ / -78 - 20 °C

3: H₂O₂; i-Pr₂NEt / benzonitrile / 15 h / 0 - 4 °C

4: 97 percent / H₂ / Pd-c / methanol

5: 75 percent / i-Pr₂NEt; HATU / CH₂Cl₂ / 8 h / 20 °C

With 1H-imidazole; oxalyl dichloride; hydrogen; dihydrogen peroxide; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; benzonitrile; 1: Substitution / 2: Swern oxidation / 3: Epoxidation / 4: Hydrogenolysis / 5: Substitution;

DOI:10.1016/S0968-0896(98)00089-3

upstream raw materials:

(2S,4S)-4-amino-2-tert-butyldimethylsiloxymethyl-3-oxo-6-methyl-1,2-oxiranylheptane

(S)-[O-tertbutyldiphenylsiloxymethyl-N-(6-N-fluorenylmethoxycarbonylamino)hexanoyl]serine

N-carbobenzoxy-L-leucinal

tert-butyldimethylsilyl chloride