N^α-(9-fluorenylmethoxycarbony)-O-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-galactopyranosyl)-L-threonine tert-butyl ester

Base Information

• Chemical Name: N^α-(9-fluorenylmethoxycarbony)-O-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-galactopyranosyl)-L-threonine tert-butyl ester
• CAS No.: 120173-56-0
• Molecular Formula: C₃₇H₄₆N₂O₁₃
• Molecular Weight: 726.778
• Mol file: 120173-56-0.mol

Synonyms:N^α-(9-fluorenylmethoxycarbony)-O-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-galactopyranosyl)-L-threonine tert-butyl ester

Chemical Property of N^α-(9-fluorenylmethoxycarbony)-O-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-galactopyranosyl)-L-threonine tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N^α-(9-fluorenylmethoxycarbony)-O-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-galactopyranosyl)-L-threonine tert-butyl ester

There total 1 articles about N^α-(9-fluorenylmethoxycarbony)-O-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-galactopyranosyl)-L-threonine tert-butyl 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:

Fmoc-Thr-OH (73731-37-0) → Nα-(9-fluorenylmethoxycarbony)-O-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-galactopyranosyl)-L-threonine tert-butyl ester (120173-56-0)

Guidance literature:

Multi-step reaction with 3 steps

1: dicyclohexyl-carbodiimide; copper(l) chloride

2: silver (II) carbonate; silver perchlorate

3: acetic acid; zinc

With silver (II) carbonate; silver perchlorate; acetic acid; dicyclohexyl-carbodiimide; copper(l) chloride; zinc; 2: Koenigs-Knorr synthesis;

DOI:10.1002/ejoc.201100304

Reference yield:

Nα-(9-fluorenylmethoxycarbony)-O-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-galactopyranosyl)-L-threonine tert-butyl ester (120173-56-0) → N-fluorenylmethoxycarbonyl-O-(2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-L-threonine tert-butyl ester (638207-70-2)

Guidance literature:

Multi-step reaction with 2 steps

1: MeONa / methanol / 3 h / pH 8.5

2: 1.18 g / p-TsOH / acetonitrile / 15 h / 20 °C / pH 4

With sodium methylate; toluene-4-sulfonic acid; In methanol; acetonitrile;

DOI:10.1002/chem.200400228

Reference yield:

Nα-(9-fluorenylmethoxycarbony)-O-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-galactopyranosyl)-L-threonine tert-butyl ester (120173-56-0) → N-fluorenylmethoxycarbonyl-O-(2-acetamido-2-deoxy-4,6-O-benzylidene-3-O-[6-O-benzyl-β-D-galactopyranosyl]-α-D-galactopyranosyl)-L-threonine tert-butyl ester (638207-72-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: MeONa / methanol / 3 h / pH 8.5

2.1: 1.18 g / p-TsOH / acetonitrile / 15 h / 20 °C / pH 4

3.1: 4 Angstroem molecular sieves / CH₂Cl₂ / 0.33 h / 20 °C

3.2: N-iodosuccinimide / CH₂Cl₂ / 0.33 h / 0 °C

3.3: 52 percent / trifluoromethanesulfonic acid / CH₂Cl₂ / 20 h / 20 °C

4.1: 62 percent / NaOMe / methanol / 12 h / pH 8.5

With 4 A molecular sieve; sodium methylate; toluene-4-sulfonic acid; In methanol; dichloromethane; acetonitrile;

DOI:10.1002/chem.200400228

upstream raw materials:

Fmoc-Thr-OH

Downstream raw materials:

N-(9H-fluoren-9-yl)methoxycarbonyl-O-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-threonine

N-fluorenylmethoxycarbonyl-O-(2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-L-threonine tert-butyl ester

N-fluorenylmethoxycarbonyl-O-(2-acetamido-2-deoxy-4,6-O-benzylidene-3-O-[6-O-benzyl-β-D-galactopyranosyl]-α-D-galactopyranosyl)-L-threonine tert-butyl ester

N-fluorenylmethoxycarbonyl-O-(2-acetamido-4,6-O-benzylidene-2-desoxy-3-O-[2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl]-α-D-galactopyranosyl)-L-threonine tert-butyl ester

Refernces

• 1、 Stra?burger, David,Glaffig, Markus,Stergiou, Natascha,Bialas, Sabrina,Besenius, Pol,Schmitt, Edgar,Kunz, Horst. "Synthetic MUC1 antitumor vaccine with incorporated 2,3-sialyl-T carbohydrate antigen inducing strong immune responses with isotype specificity". . p. 1142 - 1146. Retrieved 2018/10/21.
• 2、 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". . p. 3685 - 3689. Retrieved 2011/09/21.