N-[2-(N-tert-butyloxycarbonylamino)-2-(S-tritylthiomethyl)ethyl]glycine methyl ester

Base Information

• Chemical Name: N-[2-(N-tert-butyloxycarbonylamino)-2-(S-tritylthiomethyl)ethyl]glycine methyl ester
• CAS No.: 868611-55-6
• Molecular Formula: C₃₀H₃₆N₂O₄S
• Molecular Weight: 520.693
• Mol file: 868611-55-6.mol

Synonyms:N-[2-(N-tert-butyloxycarbonylamino)-2-(S-tritylthiomethyl)ethyl]glycine methyl ester

Chemical Property of N-[2-(N-tert-butyloxycarbonylamino)-2-(S-tritylthiomethyl)ethyl]glycine methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[2-(N-tert-butyloxycarbonylamino)-2-(S-tritylthiomethyl)ethyl]glycine methyl ester

There total 3 articles about N-[2-(N-tert-butyloxycarbonylamino)-2-(S-tritylthiomethyl)ethyl]glycine methyl 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: 72.0%

glycine ethyl ester hydrochloride (5680-79-5,883886-67-7) + N-α-(tert-butoxycarbonyl)-S-(triphenylmethyl)-L-cysteinal (149910-63-4) → N-[2-(N-tert-butyloxycarbonylamino)-2-(S-tritylthiomethyl)ethyl]glycine methyl ester (868611-55-6)

Guidance literature:

With sodium cyanoborohydride; In methanol; at 20 ℃; for 14h;

DOI:10.1021/ol051489+

Reference yield:

N-tert-butyloxycarbonyl-S-trityl-L-cysteine (21947-98-8,87494-13-1) → N-[2-(N-tert-butyloxycarbonylamino)-2-(S-tritylthiomethyl)ethyl]glycine methyl ester (868611-55-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: N-methylmorpholine; ClCO₂iBu / CH₂Cl₂ / 0.25 h / -15 °C

1.2: 97 percent / CH₂Cl₂ / 16 h / 20 °C

2.1: 92 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / 0 °C

3.1: 72 percent / NaBH₃CN / methanol / 14 h / 20 °C

With 4-methyl-morpholine; lithium aluminium tetrahydride; sodium cyanoborohydride; isobutyl chloroformate; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/ol051489+

Reference yield:

(R)-N-methyl-N-methoxy-2-tert-butoxycarbonylamino-3-(triphenylmethylthio)propionamide (158861-38-2) → N-[2-(N-tert-butyloxycarbonylamino)-2-(S-tritylthiomethyl)ethyl]glycine methyl ester (868611-55-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / 0 °C

2: 72 percent / NaBH₃CN / methanol / 14 h / 20 °C

With lithium aluminium tetrahydride; sodium cyanoborohydride; In tetrahydrofuran; methanol;

DOI:10.1021/ol051489+

upstream raw materials:

glycine ethyl ester hydrochloride

N-α-(tert-butoxycarbonyl)-S-(triphenylmethyl)-L-cysteinal

N-tert-butyloxycarbonyl-S-trityl-L-cysteine

(R)-N-methyl-N-methoxy-2-tert-butoxycarbonylamino-3-(triphenylmethylthio)propionamide

Downstream raw materials:

[[(6-benzyloxycarbonylamino-purin-9-yl)-acetyl]-(2-tert-butoxycarbonylamino-3-tritylsulfanyl-propyl)-amino]-acetic acid methyl ester

[[(6-benzyloxycarbonylamino-purin-9-yl)-acetyl]-(2-tert-butoxycarbonylamino-3-tritylsulfanyl-propyl)-amino]-acetic acid