2,17-Dioxa-4,9,15-triazanonadecane-5,10,14-tricarboxylic acid, 1-(9H-fluoren-9-yl)-18,18-dimethyl-3,8,16-trioxo-, 10,14-bis(1,1-dimethylethyl) 5-(phenylmethyl) ester, (5S,10S,14R)-

Base Information

• Chemical Name: 2,17-Dioxa-4,9,15-triazanonadecane-5,10,14-tricarboxylic acid, 1-(9H-fluoren-9-yl)-18,18-dimethyl-3,8,16-trioxo-, 10,14-bis(1,1-dimethylethyl) 5-(phenylmethyl) ester, (5S,10S,14R)-
• CAS No.: 849799-01-5
• Molecular Formula: C₄₇H₆₁N₃O₁₁
• Molecular Weight: 844.015
• Mol file: 849799-01-5.mol

Synonyms:

Chemical Property of 2,17-Dioxa-4,9,15-triazanonadecane-5,10,14-tricarboxylic acid, 1-(9H-fluoren-9-yl)-18,18-dimethyl-3,8,16-trioxo-, 10,14-bis(1,1-dimethylethyl) 5-(phenylmethyl) ester, (5S,10S,14R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,17-Dioxa-4,9,15-triazanonadecane-5,10,14-tricarboxylic acid, 1-(9H-fluoren-9-yl)-18,18-dimethyl-3,8,16-trioxo-, 10,14-bis(1,1-dimethylethyl) 5-(phenylmethyl) ester, (5S,10S,14R)-

There total 3 articles about 2,17-Dioxa-4,9,15-triazanonadecane-5,10,14-tricarboxylic acid, 1-(9H-fluoren-9-yl)-18,18-dimethyl-3,8,16-trioxo-, 10,14-bis(1,1-dimethylethyl) 5-(phenylmethyl) ester, (5S,10S,14R)- 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: 86.0%

(R)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-(benzyloxy)-5-oxopentanoic acid (104091-10-3) + 2-amino-6-tert-butoxycarbonylamino-hept-3-enedioic acid di-tert-butyl ester → 2-[4-benzyloxycarbonyl-4-(9H-fluoren-9-ylmethoxycarbonylamino)-butyrylamino]-6-tert-butoxycarbonylamino-heptanedioic acid di-tert-butyl ester (849799-01-5)

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;

DOI:10.1016/j.tetlet.2005.01.062

Reference yield:

tert-butyl N-[(benzyloxy)carbonyl]-L-homoserinate (78266-81-6) → 2-[4-benzyloxycarbonyl-4-(9H-fluoren-9-ylmethoxycarbonylamino)-butyrylamino]-6-tert-butoxycarbonylamino-heptanedioic acid di-tert-butyl ester (849799-01-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 2-nitrophenyl selenocyanate; tributylphosphine / tetrahydrofuran

1.2: 55 percent / aq. H₂O₂ / tetrahydrofuran

2.1: 55 percent / Grubb's second-generation catalyst / CH₂Cl₂ / 20 °C

3.1: H₂ / Pd/C / CH₂Cl₂; aq. ethanol

4.1: 86 percent / HATU; DIEA

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; ortho-nitrophenyl selenocyanate; tributylphosphine; hydrogen; 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; ethanol; dichloromethane;

DOI:10.1016/j.tetlet.2005.01.062

Reference yield:

2-benzyloxycarbonylamino-6-tert-butoxycarbonylamino-hept-3-enedioic acid di-tert-butyl ester → 2-[4-benzyloxycarbonyl-4-(9H-fluoren-9-ylmethoxycarbonylamino)-butyrylamino]-6-tert-butoxycarbonylamino-heptanedioic acid di-tert-butyl ester (849799-01-5)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / Pd/C / CH₂Cl₂; aq. ethanol

2: 86 percent / HATU; DIEA

With hydrogen; 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 ethanol; dichloromethane;

DOI:10.1016/j.tetlet.2005.01.062

upstream raw materials:

(R)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-(benzyloxy)-5-oxopentanoic acid

tert-butyl N-[(benzyloxy)carbonyl]-L-homoserinate

Downstream raw materials:

γ-D-Glutamyl-L-meso-diaminopimelic acid dipeptide