methyl (S)-2-[(S)-2-[(3S,4S)-4-azido-3-tert-butoxycarbonylmethoxy-5-(4-tert-butoxyphenyl)pentylamino]-3-phenylpropionylamino]-4-methylpentanoate

Base Information

• Chemical Name: methyl (S)-2-[(S)-2-[(3S,4S)-4-azido-3-tert-butoxycarbonylmethoxy-5-(4-tert-butoxyphenyl)pentylamino]-3-phenylpropionylamino]-4-methylpentanoate
• CAS No.: 246158-12-3
• Molecular Formula: C₃₇H₅₅N₅O₇
• Molecular Weight: 681.873

Synonyms:methyl (S)-2-[(S)-2-[(3S,4S)-4-azido-3-tert-butoxycarbonylmethoxy-5-(4-tert-butoxyphenyl)pentylamino]-3-phenylpropionylamino]-4-methylpentanoate

Chemical Property of methyl (S)-2-[(S)-2-[(3S,4S)-4-azido-3-tert-butoxycarbonylmethoxy-5-(4-tert-butoxyphenyl)pentylamino]-3-phenylpropionylamino]-4-methylpentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (S)-2-[(S)-2-[(3S,4S)-4-azido-3-tert-butoxycarbonylmethoxy-5-(4-tert-butoxyphenyl)pentylamino]-3-phenylpropionylamino]-4-methylpentanoate

There total 16 articles about methyl (S)-2-[(S)-2-[(3S,4S)-4-azido-3-tert-butoxycarbonylmethoxy-5-(4-tert-butoxyphenyl)pentylamino]-3-phenylpropionylamino]-4-methylpentanoate 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: 90.0%

L-phenylalanyl-L-leucine methyl ester (38155-19-0) + tert-butyl [(1S,2S)-2-azido-3-(4-tert-butoxyphenyl)-1-(2-oxoethyl)propoxy]acetate (246158-11-2) → methyl (S)-2-[(S)-2-[(3S,4S)-4-azido-3-tert-butoxycarbonylmethoxy-5-(4-tert-butoxyphenyl)pentylamino]-3-phenylpropionylamino]-4-methylpentanoate (246158-12-3)

Guidance literature:

With sodium tris(acetoxy)borohydride; triethylamine; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1016/S0040-4039(99)01216-2

Reference yield:

bromoacetic acid tert-butyl ester (5292-43-3) → methyl (S)-2-[(S)-2-[(3S,4S)-4-azido-3-tert-butoxycarbonylmethoxy-5-(4-tert-butoxyphenyl)pentylamino]-3-phenylpropionylamino]-4-methylpentanoate (246158-12-3)

Guidance literature:

Multi-step reaction with 4 steps

1: NaOH; NBu₄HSO₄ / benzene; H₂O / 1 h

2: 0.88 g / N-methylmorpholine oxide; OsO₄ / H₂O; acetone; tetrahydrofuran / 10 h

3: 85 percent / Na₂CO₃; Pb(OAc)4 / benzene / 3 h / 20 °C

4: 82 percent / triethylamine; NaBH(OAc)3 / 1,2-dichloro-ethane / 45 h

With lead(IV) acetate; sodium hydroxide; osmium(VIII) oxide; tetra(n-butyl)ammonium hydrogensulfate; sodium tris(acetoxy)borohydride; sodium carbonate; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; water; 1,2-dichloro-ethane; acetone; benzene;

DOI:10.1021/jo0356863

Reference yield:

(2S,3S)-2-amino-1-(4-tert-butoxyphenyl)hex-5-en-3-ol (246158-06-5) → methyl (S)-2-[(S)-2-[(3S,4S)-4-azido-3-tert-butoxycarbonylmethoxy-5-(4-tert-butoxyphenyl)pentylamino]-3-phenylpropionylamino]-4-methylpentanoate (246158-12-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 85 percent / 4-(dimethylamino)pyridine; CuSO₄; triflyl azide / CH₂Cl₂ / 2 h

2: NaOH; NBu₄HSO₄ / benzene; H₂O / 1 h

3: 0.88 g / N-methylmorpholine oxide; OsO₄ / H₂O; acetone; tetrahydrofuran / 10 h

4: 85 percent / Na₂CO₃; Pb(OAc)4 / benzene / 3 h / 20 °C

5: 82 percent / triethylamine; NaBH(OAc)3 / 1,2-dichloro-ethane / 45 h

With lead(IV) acetate; dmap; sodium hydroxide; osmium(VIII) oxide; triflic azide; tetra(n-butyl)ammonium hydrogensulfate; sodium tris(acetoxy)borohydride; sodium carbonate; copper(II) sulfate; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; dichloromethane; water; 1,2-dichloro-ethane; acetone; benzene;

DOI:10.1021/jo0356863

upstream raw materials:

L-phenylalanyl-L-leucine methyl ester

tert-butyl [(1S,2S)-2-azido-3-(4-tert-butoxyphenyl)-1-(2-oxoethyl)propoxy]acetate

bromoacetic acid tert-butyl ester

N-(benzyloxycarbonyl)-O-(1,1-dimethylethyl)-L-tyrosine

Downstream raw materials:

methyl (S)-2-((S)-2-[(S)-10-[(S)-1-azido-2-(4-hydroxyphenyl)ethyl]-3,6-dioxo[1,4,7]oxadiazecan-7-yl]-3-phenylpropionylamino)-4-methylpentanoate

methyl (S)-2-((S)-2-[[(3S,4S)-4-azido-3-carboxymethoxy-5-(4-hydroxyphenyl)pentyl][2-(9H-fluoren-9-ylmethoxycarbonylamino)acetyl]amino]-3-phenylpropionylamino)-4-methylpentanoate

(S)-2-((S)-2-{[(3S,4S)-4-Azido-5-(4-hydroxy-phenyl)-3-pentafluorophenyloxycarbonylmethoxy-pentyl]-[2-(9H-fluoren-9-ylmethoxycarbonylamino)-acetyl]-amino}-3-phenyl-propionylamino)-4-methyl-pentanoic acid methyl ester

(S)-2-((S)-2-{(S)-10-[(S)-1-Amino-2-(4-hydroxy-phenyl)-ethyl]-3,6-dioxo-[1,4,7]oxadiazecan-7-yl}-3-phenyl-propionylamino)-4-methyl-pentanoic acid methyl ester

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