N-9-fuorenylmethoxycarbonyl-(2S,4R)-4-methylprolyl-(2S,4S)-4-methylprolyl-glycine benzyl ester

Base Information

• Chemical Name: N-9-fuorenylmethoxycarbonyl-(2S,4R)-4-methylprolyl-(2S,4S)-4-methylprolyl-glycine benzyl ester
• CAS No.: 901139-63-7
• Molecular Formula: C₃₆H₃₉N₃O₆
• Molecular Weight: 609.722
• Mol file: 901139-63-7.mol

Synonyms:N-9-fuorenylmethoxycarbonyl-(2S,4R)-4-methylprolyl-(2S,4S)-4-methylprolyl-glycine benzyl ester

Chemical Property of N-9-fuorenylmethoxycarbonyl-(2S,4R)-4-methylprolyl-(2S,4S)-4-methylprolyl-glycine benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-9-fuorenylmethoxycarbonyl-(2S,4R)-4-methylprolyl-(2S,4S)-4-methylprolyl-glycine benzyl ester

There total 9 articles about N-9-fuorenylmethoxycarbonyl-(2S,4R)-4-methylprolyl-(2S,4S)-4-methylprolyl-glycine benzyl 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:

C15H20N2O3*ClH + (2S,4R)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-4-methylpyrrolidine-2-carboxylic acid (333777-34-7,1228577-03-4) → N-9-fuorenylmethoxycarbonyl-(2S,4R)-4-methylprolyl-(2S,4S)-4-methylprolyl-glycine benzyl ester (901139-63-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; In dichloromethane; at 0 - 20 ℃; for 40h;

Reference yield:

(S)-2-tert-butyldimethylsilyloxymethyl-N-tert-butyloxycarbonyl-4-methylenepyrrolidine → N-9-fuorenylmethoxycarbonyl-(2S,4R)-4-methylprolyl-(2S,4S)-4-methylprolyl-glycine benzyl ester (901139-63-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: hydrogen / Raney-nickel / methanol

1.2: TBAF / tetrahydrofuran

2.1: 94 percent / NaClO₂; NaOCl; TEMPO / aq. phosphate buffer; acetonitrile / 18 h / 40 °C

3.1: 84 percent / PyBOP; DIEA / CH₂Cl₂ / 27 h

4.1: HCl / dioxane / 2.5 h

5.1: 520 mg / DIEA; PyBroP / CH₂Cl₂ / 40 h / 20 °C

With hydrogenchloride; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; nickel; In 1,4-dioxane; methanol; phosphate buffer; dichloromethane; acetonitrile;

DOI:10.1021/ja061793d

Reference yield:

(2S,4S)-4-methylprolyl-glycine benzyl ester + (2S,4R)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-4-methylpyrrolidine-2-carboxylic acid (333777-34-7,1228577-03-4) → N-9-fuorenylmethoxycarbonyl-(2S,4R)-4-methylprolyl-(2S,4S)-4-methylprolyl-glycine benzyl ester (901139-63-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; In dichloromethane; at 20 ℃; for 40h;

DOI:10.1021/ja061793d

upstream raw materials:

(2S,4R)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-4-methylpyrrolidine-2-carboxylic acid

N-tert-Butyloxycarbonyl-(2S,4S)-4-methylproline

N-tert-butyloxycarbonyl-(2S,4S)-4-methylprolyl-glycine benzyl ester

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide