(R)-2-Benzyloxycarbonylamino-3-hydroxy-propionic acid 9,10-dioxo-9,10-dihydro-anthracen-2-ylmethyl ester

Base Information

• Chemical Name: (R)-2-Benzyloxycarbonylamino-3-hydroxy-propionic acid 9,10-dioxo-9,10-dihydro-anthracen-2-ylmethyl ester
• CAS No.: 75299-15-9
• Molecular Formula: C₂₆H₂₁NO₇
• Molecular Weight: 459.455
• Mol file: 75299-15-9.mol

Synonyms:(R)-2-Benzyloxycarbonylamino-3-hydroxy-propionic acid 9,10-dioxo-9,10-dihydro-anthracen-2-ylmethyl ester

Chemical Property of (R)-2-Benzyloxycarbonylamino-3-hydroxy-propionic acid 9,10-dioxo-9,10-dihydro-anthracen-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-Benzyloxycarbonylamino-3-hydroxy-propionic acid 9,10-dioxo-9,10-dihydro-anthracen-2-ylmethyl ester

There total 1 articles about (R)-2-Benzyloxycarbonylamino-3-hydroxy-propionic acid 9,10-dioxo-9,10-dihydro-anthracen-2-ylmethyl 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: 92.0%

N-(benzyloxycarbonyl)-D-serine (6081-61-4) + 2-(bromomethyl)anthraquinone (7598-10-9) → (R)-2-Benzyloxycarbonylamino-3-hydroxy-propionic acid 9,10-dioxo-9,10-dihydro-anthracen-2-ylmethyl ester (75299-15-9)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene;

DOI:10.1021/jo01312a049

Reference yield: 100.0%

N-(benzoyloxycarbonyl)-O-(tetrahydropyranyl)-D-serine (75299-16-0) + (R)-2-Benzyloxycarbonylamino-3-hydroxy-propionic acid 9,10-dioxo-9,10-dihydro-anthracen-2-ylmethyl ester (75299-15-9) → (R)-2-Benzyloxycarbonylamino-3-(tetrahydro-pyran-2-yloxy)-propionic acid (R)-2-benzyloxycarbonylamino-2-(9,10-dioxo-9,10-dihydro-anthracen-2-ylmethoxycarbonyl)-ethyl ester (78089-11-9)

Guidance literature:

With 4-methyl-morpholine; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; 1.) 1h, 5 deg C, 1h, r.t., 2.) 20h, r.t.;

DOI:10.1021/jo00331a001

Reference yield:

(R)-2-Benzyloxycarbonylamino-3-hydroxy-propionic acid 9,10-dioxo-9,10-dihydro-anthracen-2-ylmethyl ester (75299-15-9) → ((3R,7R,11R)-7,11-Bis-benzyloxycarbonylamino-2,6,10-trioxo-1,5,9-trioxa-cyclododec-3-yl)-carbamic acid benzyl ester (75363-09-6)

Guidance literature:

Multi-step reaction with 6 steps

1: pyridinium p-toluenesulfonate / CH₂Cl₂ / 2 h / Ambient temperature

2: 82 percent / N-methylmorpholine / propan-2-ol / 4 h / Irradiation

3: 100 percent / 1.) N-hydroxybenzotriazole, N,N'-dicyclohexylcarbodiimide, 2.) N-methylmorpholine / tetrahydrofuran / 1.) 1h, 5 deg C, 1h, r.t., 2.) 20h, r.t.

4: 95 percent / pyridinium p-toluenesulfonate / CHCl₃; ethanol / 23 h / 55 °C

5: 67 percent / N-methylmorpholine / propan-2-ol; CHCl₃ / 4.5 h / Irradiation

6: 10 percent / 4-tert-butyl-N-isopropylimidazolyl disulfide, triphenylphosphine / CH₂Cl₂ / 0.25 h / Ambient temperature

With 4-methyl-morpholine; pyridinium p-toluenesulfonate; benzotriazol-1-ol; dicyclohexyl-carbodiimide; triphenylphosphine; bis(4-tert-butyl-1-iso-propyl-1H-imidazol-2-yl)disulfide; In tetrahydrofuran; ethanol; dichloromethane; chloroform; isopropyl alcohol;

DOI:10.1021/jo00331a001

upstream raw materials:

N-(benzyloxycarbonyl)-D-serine

2-(bromomethyl)anthraquinone

Downstream raw materials:

(R)-2-Benzyloxycarbonylamino-3-(tetrahydro-pyran-2-yloxy)-propionic acid 9,10-dioxo-9,10-dihydro-anthracen-2-ylmethyl ester

N-(benzoyloxycarbonyl)-O-(tetrahydropyranyl)-D-serine

(R)-2-Benzyloxycarbonylamino-3-(tetrahydro-pyran-2-yloxy)-propionic acid (R)-2-benzyloxycarbonylamino-2-(9,10-dioxo-9,10-dihydro-anthracen-2-ylmethoxycarbonyl)-ethyl ester

(R)-2-Benzyloxycarbonylamino-3-hydroxy-propionic acid (R)-2-benzyloxycarbonylamino-2-(9,10-dioxo-9,10-dihydro-anthracen-2-ylmethoxycarbonyl)-ethyl ester

Refernces

• 1、 Rastetter,Erickson,Venuti. "Synthesis of iron chelators. Enterobactin, enantioenterobactin, and a chiral analogue". . p. 3579 - 3590. Retrieved 2007/10/02.