Fmoc-L-Ser[alpha-(Gal-beta(1-3)-GalNAc)]-OH peracetate

Base Information

• Chemical Name: Fmoc-L-Ser[alpha-(Gal-beta(1-3)-GalNAc)]-OH peracetate
• CAS No.: 125760-30-7
• Molecular Formula: C44H52N2O21
• Molecular Weight: 944.88
• Mol file: 125760-30-7.mol

Synonyms:Fmoc-L-Ser[alpha-(Gal-beta(1-3)-GalNAc)]-OH peracetate;O-[4,6-Di-O-acetyl-2-(acetylamino)-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-alpha-D-galactopyranosyl]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-serine

Chemical Property of Fmoc-L-Ser[alpha-(Gal-beta(1-3)-GalNAc)]-OH peracetate

Chemical Property:

• Boiling Point: 995.1±65.0 °C(Predicted)
• PKA: 3.34±0.10(Predicted)
• PSA: 299.45000
• Density: 1.42±0.1 g/cm3(Predicted)
• LogP: 1.96940

Purity/Quality:

2-Acetamido-3-O-(2,3,4,6-tetra-O-acetyl-b-D-galactopyranosyl)-4,6-di-O-acetyl-2-deoxy-a-D-galactopyranosyl-Fmoc-L- serine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Fmoc-L-Ser[alpha-(Gal-beta(1-3)-GalNAc)]-OH peracetate

There total 18 articles about Fmoc-L-Ser[alpha-(Gal-beta(1-3)-GalNAc)]-OH peracetate 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: 84.0%

N-(9H-fluoren-9-yl)methoxycarbonyl-O-(2-acetamido-4,6-di-O-acetyl-2-deoxy-3-O-[2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl]-α-D-galactopyranosyl)-L-serine tert-butyl ester (658072-67-4) → N-(9H-fluoren-9-yl)methoxycarbonyl-O-(2-acetamido-4,6-di-O-acetyl-2-deoxy-3-O-[2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl]α-D-galactopyranosyl)-L-serine (125760-30-7)

Guidance literature:

With trifluoroacetic acid; In methoxybenzene; at 20 ℃; for 1h;

DOI:10.1055/s-2003-42429

Reference yield:

N-(9H-fluoren-9-yl-methoxycarbonyl)-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-serine tert-butyl ester (912840-54-1) → N-(9H-fluoren-9-yl)methoxycarbonyl-O-(2-acetamido-4,6-di-O-acetyl-2-deoxy-3-O-[2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl]α-D-galactopyranosyl)-L-serine (125760-30-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 77 percent / p-toluenesulfonic acid / acetonitrile / 20 °C

2: 66 percent / Hg(CN)2 / CH₂Cl₂; nitromethane / 14 h / 20 °C

3: 90 percent / acetic acid / H₂O / 1 h / 85 °C

4: 97 percent / pyridine / 18 h / 0 - 20 °C

5: 53 percent / trifluoroacetic acid / methoxybenzene / 1.5 h / 20 °C

With pyridine; mercury(II) cyanide; toluene-4-sulfonic acid; acetic acid; trifluoroacetic acid; In nitromethane; dichloromethane; water; methoxybenzene; acetonitrile;

DOI:10.1002/anie.200602494

Reference yield:

C37H42O10N2 → N-(9H-fluoren-9-yl)methoxycarbonyl-O-(2-acetamido-4,6-di-O-acetyl-2-deoxy-3-O-[2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl]α-D-galactopyranosyl)-L-serine (125760-30-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 66 percent / Hg(CN)2 / CH₂Cl₂; nitromethane / 14 h / 20 °C

2: 90 percent / acetic acid / H₂O / 1 h / 85 °C

3: 97 percent / pyridine / 18 h / 0 - 20 °C

4: 53 percent / trifluoroacetic acid / methoxybenzene / 1.5 h / 20 °C

With pyridine; mercury(II) cyanide; acetic acid; trifluoroacetic acid; In nitromethane; dichloromethane; water; methoxybenzene;

DOI:10.1002/anie.200602494

upstream raw materials:

acetic anhydride

(S)-3-[(2S,3R,4R,5R,6R)-5-Acetoxy-6-acetoxymethyl-3-azido-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid

N-(9H-fluoren-9-yl)methoxycarbonyl-O-(2-acetamido-4,6-di-O-acetyl-2-deoxy-3-O-[2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl]-α-D-galactopyranosyl)-L-serine tert-butyl ester

N-(9H-fluoren-9-yl-methoxycarbonyl)-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-serine tert-butyl ester

Refernces

• 1、 Cai, Hui,Huang, Zhi-Hua,Shi, Lei,Zou, Peng,Zhao, Yu-Fen,Kunz, Horst,Li, Yan-Mei. "Synthesis of Tn/T antigen MUC1 glycopeptide BSA conjugates and their evaluation as vaccines". scheme or table. p. 3685 - 3689. Retrieved 2011/09/21.
• 2、 Reipen, Tanja,Kunz, Horst. "Synthesis of Peptide and Glycopeptide Partial Structures of the Homophilic Recognition Domain of Epithelial Cadherin". . p. 2487 - 2502. Retrieved 2007/10/03.