(S)-2-tert-Butoxycarbonylamino-3-(4-methoxy-benzylsulfanyl)-propionic acid (1S,2S,6R,7R)-3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-4-yl ester

Base Information

• Chemical Name: (S)-2-tert-Butoxycarbonylamino-3-(4-methoxy-benzylsulfanyl)-propionic acid (1S,2S,6R,7R)-3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-4-yl ester
• CAS No.: 180415-70-7
• Molecular Formula: C₂₅H₃₂N₂O₇S
• Molecular Weight: 504.604
• Mol file: 180415-70-7.mol

Synonyms:

Chemical Property of (S)-2-tert-Butoxycarbonylamino-3-(4-methoxy-benzylsulfanyl)-propionic acid (1S,2S,6R,7R)-3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-tert-Butoxycarbonylamino-3-(4-methoxy-benzylsulfanyl)-propionic acid (1S,2S,6R,7R)-3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-4-yl ester

There total 1 articles about (S)-2-tert-Butoxycarbonylamino-3-(4-methoxy-benzylsulfanyl)-propionic acid (1S,2S,6R,7R)-3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-4-yl 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:

N-hydroxy-5-norbornene-endo-2,3-dicarboxamide (68330-42-7) + N-tert-butyloxycarbonyl-S-p-methoxybenzyl-D-cysteine (58290-35-0) → (S)-2-tert-Butoxycarbonylamino-3-(4-methoxy-benzylsulfanyl)-propionic acid (1S,2S,6R,7R)-3,5-dioxo-4-aza-tricyclo[5.2.1.02,6]dec-4-yl ester (180415-70-7)

Guidance literature:

With dicyclohexyl-carbodiimide; In tetrahydrofuran;

DOI:10.1016/S0960-894X(96)00270-3

Reference yield:

(S)-2-tert-Butoxycarbonylamino-3-(4-methoxy-benzylsulfanyl)-propionic acid (1S,2S,6R,7R)-3,5-dioxo-4-aza-tricyclo[5.2.1.02,6]dec-4-yl ester (180415-70-7) → Benzyloxycarbonylamino-thioacetic acid S-[(S)-2-tert-butoxycarbonylamino-3-(4-methoxy-2-oxo-2,5-dihydro-pyrrol-1-yl)-3-oxo-propyl] ester (180415-73-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) NaH / 1.) THF, reflux, 30 min, 2.) THF, 0 deg C

2: 1.) Hg(CF₃CO₂)2, 2.) H₂S / 1.) AcOH, 2.) AcOH, 10 min

3: 73 percent / Et₃N / tetrahydrofuran

With Hg(II) trifluoroacetate; hydrogen sulfide; sodium hydride; triethylamine; In tetrahydrofuran;

DOI:10.1016/S0960-894X(96)00270-3

Reference yield:

4-methoxy-3-pyrrolin-2-one (69778-83-2) + (S)-2-tert-Butoxycarbonylamino-3-(4-methoxy-benzylsulfanyl)-propionic acid (1S,2S,6R,7R)-3,5-dioxo-4-aza-tricyclo[5.2.1.02,6]dec-4-yl ester (180415-70-7) → [(S)-1-(4-Methoxy-benzylsulfanylmethyl)-2-(4-methoxy-2-oxo-2,5-dihydro-pyrrol-1-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester (180415-71-8)

Guidance literature:

With sodium hydride; Yield given. Multistep reaction; 1.) THF, reflux, 30 min, 2.) THF, 0 deg C;

DOI:10.1016/S0960-894X(96)00270-3

upstream raw materials:

N-hydroxy-5-norbornene-endo-2,3-dicarboxamide

N-tert-butyloxycarbonyl-S-p-methoxybenzyl-D-cysteine

Downstream raw materials:

[(S)-1-(4-Methoxy-benzylsulfanylmethyl)-2-(4-methoxy-2-oxo-2,5-dihydro-pyrrol-1-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester

Benzyloxycarbonylamino-thioacetic acid S-[(S)-2-tert-butoxycarbonylamino-3-(4-methoxy-2-oxo-2,5-dihydro-pyrrol-1-yl)-3-oxo-propyl] ester