Fmoc-L-Asn(GlcNAc(Ac)3-beta)-OH

Base Information

• Chemical Name: Fmoc-L-Asn(GlcNAc(Ac)3-beta)-OH
• CAS No.: 131287-39-3
• Molecular Formula: C33H37 N3 O13
• Molecular Weight: 683.669
• DSSTox Substance ID: DTXSID40442309
• Nikkaji Number: J666.433D
• Wikidata: Q72477981
• Mol file: 131287-39-3.mol

Synonyms:131287-39-3;Fmoc-L-Asn(GlcNAc(Ac)3-beta)-OH;Fmoc-Asn(Ac3AcNH-beta-Glc)-OH;fmoc-asn(glcnac(ac)3-beta-d)-oh;Fmoc-L-Asn(beta-D-GlcNAc(Ac)3)-OH;(2S)-4-[[(2R,3R,4R,5S,6R)-3-acetamido-4,5-diacetyloxy-6-(acetyloxymethyl)oxan-2-yl]amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxobutanoic acid;Fmoc-Asn[GlcNAc(Ac)3-beta-D]-OH;glcnac l-asparagine;SCHEMBL6044028;Fmoc-Asn(GlcNAc(Ac)--D)-OH;DTXSID40442309;EX-A3853;Fmoc-Asn(GlcNAc(Ac)3-|A-D)-OH;MFCD00237079;AKOS025294293;FD21194;AS-48994;HY-141464;CS-0169635;A930302;Fmoc-L-Asn((Ac)3-beta-D-GlcNAc)-OH, >=95% (HPLC);N--Fmoc-N--(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl--D-glucopyranosyl)-L-asparagine;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-4-(((2R,3R,4R,5S,6R)-3-acetamido-4,5-diacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)amino)-4-oxobutanoic acid;(S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-((2R,3R,4R,5S,6R)-3-acetamido-4,5-diacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-ylamino)-4-oxobutanoic acid;N-alpha-(9-Fluorenylmethyloxycarbonyl)-N-gamma-(2-acetamido-2deoxy-3,4,6-tri-O-acetyl-beta-D-galactopyranosyl)-L-asparagin (Fmoc-L-Asn(GlcNAc4)-OH);N2-(((9H-Fluoren-9-yl)methoxy)carbonyl)-N4-((2R,3R,4R,5S,6R)-3-acetamido-4,5-diacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)-L-asparagine

Chemical Property of Fmoc-L-Asn(GlcNAc(Ac)3-beta)-OH

Chemical Property:

• Boiling Point: 934.7±65.0 °C(Predicted)
• PKA: 3.81±0.10(Predicted)
• PSA: 221.96000
• Density: 1.41±0.1 g/cm3(Predicted)
• LogP: 2.31340
• Storage Temp.: -15°C
• XLogP3: 1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 16
• Exact Mass: 683.23263824
• Heavy Atom Count: 49
• Complexity: 1240

Purity/Quality:

98%Min ^*data from raw suppliers

Fmoc-ASN(Ac3AcNH-β-GLC)-OH ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1C(C(C(OC1NC(=O)CC(C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24)COC(=O)C)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1NC(=O)C[C@@H](C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24)COC(=O)C)OC(=O)C)OC(=O)C
• Uses: Fmoc-ASN(Ac3AcNH-β-GLC)-OH is a synthetic Fmoc-protected glycopeptide with enhanced recognition by glycan-?dependent HIV-?1 broadly neutralizing antibodies.

Technology Process of Fmoc-L-Asn(GlcNAc(Ac)3-beta)-OH

There total 18 articles about Fmoc-L-Asn(GlcNAc(Ac)3-beta)-OH 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%

(2R,3S,4R,5R,6R)-6-((S)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(tert-butoxy)-4-oxobutanamido)-5-acetamido-2-(acetoxymethyl)tetrahydro-2H-pyran-3,4-diyl diacetate (154395-61-6) → Nω-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-Nα-(9-fluorenylmethyloxycarbonyl))-L-asparagine (131287-39-3)

Guidance literature:

With trifluoroacetic acid; In water; at 20 ℃; for 3h;

DOI:10.1016/j.bmcl.2011.05.059

Reference yield: 85.0%

2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosylamine (4515-24-6) + N-(9-fluorenyl)methoxycarbonyl-aspartic anhydride (145038-47-7) → Nω-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-Nα-(9-fluorenylmethyloxycarbonyl))-L-asparagine (131287-39-3)

Guidance literature:

In dimethyl sulfoxide; at 20 ℃; for 1h;

DOI:10.1016/j.tetlet.2009.08.106

Reference yield:

2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl azide (6205-69-2) → Nω-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-Nα-(9-fluorenylmethyloxycarbonyl))-L-asparagine (131287-39-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 87 percent / H₂ / Lindlar catalyst / ethanol / 20 h / 20 °C

2: 100 percent / 2,6-di-t-butyl-4-methylpyridine / CH₂Cl₂ / 0.67 h / 20 °C

3: 82 percent / Bu₄NF / CH₂Cl₂ / 20 °C

4: TFA / CH₂Cl₂ / 1.5 h / 20 °C

With 2,6-di-tert-butyl-4-methylpyridine; tetrabutyl ammonium fluoride; hydrogen; trifluoroacetic acid; Lindlar's catalyst; In ethanol; dichloromethane; 1: Reduction / 2: Substitution / 3: Condensation / 4: Hydrolysis;

DOI:10.1016/S0040-4039(99)02228-5

upstream raw materials:

Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-tert-butoxycarbonylamino-tetrahydro-pyran-4-yl ester

C₂₄H₄₂N₂O₁₀Si

2-acetamido-2-deoxy-β-D-glucopyranosylamine

N-Acetyl-D-glucosamine

Downstream raw materials:

MEN₁₁₄₂₀

Refernces

• 1、 Toonstra, Christian,Amin, Mohammed N.,Wang, Lai-Xi. "Site-Selective Chemoenzymatic Glycosylation of an HIV-1 Polypeptide Antigen with Two Distinct N-Glycans via an Orthogonal Protecting Group Strategy". . p. 6176 - 6185. Retrieved 2016.
• 2、 Doelman, Ward,Marqvorsen, Mikkel H. S.,Chiodo, Fabrizio,Bruijns, Sven C. M.,van der Marel, Gijsbert A.,van Kooyk, Yvette,van Kasteren, Sander I.,Araman, Can. "Synthesis of Asparagine Derivatives Harboring a Lewis X Type DC-SIGN Ligand and Evaluation of their Impact on Immunomodulation in Multiple Sclerosis". . p. 2742 - 2752. Retrieved 2020/12/29.