1D-(1,2,4/3,5)-2-amino-1,2-N,O-carbonyl-3-O-<(R)-2'-propanoyl-L-alanyl-D-isoglutamine benzylester>-5-C-hydroxymethyl-1,3,4-cyclohexane-triol

Base Information

• Chemical Name: 1D-(1,2,4/3,5)-2-amino-1,2-N,O-carbonyl-3-O-<(R)-2'-propanoyl-L-alanyl-D-isoglutamine benzylester>-5-C-hydroxymethyl-1,3,4-cyclohexane-triol
• CAS No.: 121788-71-4
• Molecular Formula: C₃₃H₄₀N₄O₁₀
• Molecular Weight: 652.701
• Mol file: 121788-71-4.mol

Synonyms:1D-(1,2,4/3,5)-2-amino-1,2-N,O-carbonyl-3-O-<(R)-2'-propanoyl-L-alanyl-D-isoglutamine benzylester>-5-C-hydroxymethyl-1,3,4-cyclohexane-triol

Chemical Property of 1D-(1,2,4/3,5)-2-amino-1,2-N,O-carbonyl-3-O-<(R)-2'-propanoyl-L-alanyl-D-isoglutamine benzylester>-5-C-hydroxymethyl-1,3,4-cyclohexane-triol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1D-(1,2,4/3,5)-2-amino-1,2-N,O-carbonyl-3-O-<(R)-2'-propanoyl-L-alanyl-D-isoglutamine benzylester>-5-C-hydroxymethyl-1,3,4-cyclohexane-triol

There total 15 articles about 1D-(1,2,4/3,5)-2-amino-1,2-N,O-carbonyl-3-O-<(R)-2'-propanoyl-L-alanyl-D-isoglutamine benzylester>-5-C-hydroxymethyl-1,3,4-cyclohexane-triol 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: 78.0%

(R)-2-((3aS,4R,4aR,6R,8aR,9aS)-2-Oxo-6-phenyl-octahydro-1,5,7-trioxa-3-aza-cyclopenta[b]naphthalen-4-yloxy)-propionic acid (121788-70-3) + L-ala-D-isoglutamine benzyl ester (62853-36-5,71822-09-8,85546-24-3) → 1D-(1,2,4/3,5)-2-amino-1,2-N,O-carbonyl-3-O-<(R)-2'-propanoyl-L-alanyl-D-isoglutamine benzylester>-5-C-hydroxymethyl-1,3,4-cyclohexane-triol (121788-71-4)

Guidance literature:

With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide;

DOI:10.1021/jo00277a002

Reference yield:

(3aR,4R,5R,6R,7aS)-4,5-dihydroxy-6-(hydroxymethyl)hexahydrobenzo[d]oxazol-2(3H)-one (121788-68-9) → 1D-(1,2,4/3,5)-2-amino-1,2-N,O-carbonyl-3-O-<(R)-2'-propanoyl-L-alanyl-D-isoglutamine benzylester>-5-C-hydroxymethyl-1,3,4-cyclohexane-triol (121788-71-4)

Guidance literature:

Multi-step reaction with 3 steps

1: ZnCl₂

2: 72 percent / NaH / dimethylformamide

3: 78 percent / N-hydroxysuccinimide, dicyclohexylcarbodiimide

With 1-hydroxy-pyrrolidine-2,5-dione; sodium hydride; dicyclohexyl-carbodiimide; zinc(II) chloride; In N,N-dimethyl-formamide;

DOI:10.1021/jo00277a002

Reference yield:

1D-(1,2,4/3,5)-2-amino-1,2-N,O-carbonyl-4,7-benzylidene-5-C-hydroxymethyl-1,3,4-cyclohexanetriol (121788-69-0) → 1D-(1,2,4/3,5)-2-amino-1,2-N,O-carbonyl-3-O-<(R)-2'-propanoyl-L-alanyl-D-isoglutamine benzylester>-5-C-hydroxymethyl-1,3,4-cyclohexane-triol (121788-71-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / NaH / dimethylformamide

2: 78 percent / N-hydroxysuccinimide, dicyclohexylcarbodiimide

With 1-hydroxy-pyrrolidine-2,5-dione; sodium hydride; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide;

DOI:10.1021/jo00277a002

upstream raw materials:

(R)-2-((3aS,4R,4aR,6R,8aR,9aS)-2-Oxo-6-phenyl-octahydro-1,5,7-trioxa-3-aza-cyclopenta[b]naphthalen-4-yloxy)-propionic acid

L-ala-D-isoglutamine benzyl ester

(3aR,4R,5R,6R,7aS)-4,5-dihydroxy-6-(hydroxymethyl)hexahydrobenzo[d]oxazol-2(3H)-one

1D-(1,2,4/3,5)-2-amino-1,2-N,O-carbonyl-4,7-benzylidene-5-C-hydroxymethyl-1,3,4-cyclohexanetriol

Refernces

• 1、 Barton, Derek H. R.,Camara, Jose,Dalko, Peter,Gero, Stephen D.,Quiclet-Sire, Beatrice,Stuetz, Peter. "Synthesis of Biologically Active Carbocyclic Analogues of N-Acetylmuramyl-L-alanyl-D-isoglutamine (MDP)". . p. 3764 - 3766. Retrieved 2007/10/02.