Benzyl [(3R)-2,6-dioxooxan-3-yl]carbamate

Base Information

• Chemical Name: Benzyl [(3R)-2,6-dioxooxan-3-yl]carbamate
• CAS No.: 71869-80-2
• Molecular Formula: C13H13NO5
• Molecular Weight: 263.25
• DSSTox Substance ID: DTXSID30510061
• Wikidata: Q82368093
• Mol file: 71869-80-2.mol

Synonyms:71869-80-2;Benzyl [(3R)-2,6-dioxooxan-3-yl]carbamate;[(3R)-Tetrahydro-2,6-dioxo-2H-pyran-3-yl]-carbamic Acid Phenylmethyl;BENZYL N-[(3R)-2,6-DIOXOOXAN-3-YL]CARBAMATE;SCHEMBL10737701;DTXSID30510061

Chemical Property of Benzyl [(3R)-2,6-dioxooxan-3-yl]carbamate

Chemical Property:

• PSA: 81.70000
• LogP: 1.53590
• Solubility.: Chloroform, Dichloromethane, Glacial Acetone
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 263.07937252
• Heavy Atom Count: 19
• Complexity: 362

Purity/Quality:

95% ^*data from raw suppliers

[(3R)-Tetrahydro-2,6-dioxo-2H-pyran-3-yl]-carbamicAcidPhenylmethyl ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=O)OC(=O)C1NC(=O)OCC2=CC=CC=C2
• Isomeric SMILES: C1CC(=O)OC(=O)[C@@H]1NC(=O)OCC2=CC=CC=C2
• Uses: [(3R)-Tetrahydro-2,6-dioxo-2H-pyran-3-yl]-carbaMic Acid PhenylMethyl is used in the synthesis of Cbz-aminoglutarimides and Cbz-succinimides, for their anticonvulsant activity.

Technology Process of Benzyl [(3R)-2,6-dioxooxan-3-yl]carbamate

There total 6 articles about Benzyl [(3R)-2,6-dioxooxan-3-yl]carbamate 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: 100.0%

N-benzyloxycarbonyl-D-glutamic acid (63648-73-7) → benzyl (R)-(2,6-dioxotetrahydro-2H-pyran-3-yl)carbamate (71869-80-2)

Guidance literature:

With dicyclohexyl-carbodiimide; In tetrahydrofuran; at 20 ℃; for 20h; Inert atmosphere;

DOI:10.1016/j.tetlet.2016.11.083

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → benzyl (R)-(2,6-dioxotetrahydro-2H-pyran-3-yl)carbamate (71869-80-2)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide / water; acetone / 7 h / 0 - 20 °C

2: acetic anhydride / 2 h / 20 °C

With acetic anhydride; sodium hydroxide; In water; acetone;

DOI:10.14233/ajchem.2013.15202

Reference yield:

D-Glutamic acid (6893-26-1,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) → benzyl (R)-(2,6-dioxotetrahydro-2H-pyran-3-yl)carbamate (71869-80-2)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide / water; acetone / 7 h / 0 - 20 °C

2: acetic anhydride / 2 h / 20 °C

With acetic anhydride; sodium hydroxide; In water; acetone;

DOI:10.14233/ajchem.2013.15202

upstream raw materials:

N-benzyloxycarbonyl-D-glutamic acid

D-Glutamic acid

benzyl chloroformate

L-glutamic acid

Downstream raw materials:

N-(N-benzyloxycarbonyl-L-γ-glutamyl)-glycine

(R)-5-amino-4-(((benzyloxy)carbonyl)amino)-5-oxopentanoic acid

N-[1-(N-carbobenzoxy-γ-D-glutamyl)-3,4-dimethoxyphenyl]glycine

N-(benzyloxycarbonyl)-D-glutamyl-N'-(tert-butyloxycarbonyl)-D-lysine methyl ester

Refernces

• 1、 Brethon, Anne,Bouix-Peter, Claire,Clary, Laurence,Fournier, Jean-Fran?ois,Harris, Craig S.,Lardy, Claude,Roche, Didier,Rodeschini, Vincent,Talano, Sandrine. "An expedient synthesis of non-racemic N-alkylated pyrrolidin-2,5-diones and piperidin-2,6-diones as peptidomimetics". supporting information. p. 5924 - 5927. Retrieved 2016/12/09.
• 2、 Manesis, Nick J.,Goodman, Murray. "Synthesis of a Novel Class of Peptides: Dilactam-Bridged Tetrapeptides". . p. 5331 - 5341. Retrieved 2007/10/02.