FMOC-THR(GALNAC(AC)3-ALPHA-D)-OH

Base Information

• Chemical Name: FMOC-THR(GALNAC(AC)3-ALPHA-D)-OH
• CAS No.: 116783-35-8
• Molecular Formula: C33H38N2O13
• Molecular Weight: 670.67
• Hs Code.: 2932 99 00
• Mol file: 116783-35-8.mol

Synonyms:17:PN: WO2007079448 PAGE: 38 claimed sequence;Fmoc-Thr(galnac(Ac)3-alpha-D)-OH;N-Fmoc-O-beta-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-alpha-D-galactopyranosyl)-L-threonine;

Chemical Property of FMOC-THR(GALNAC(AC)3-ALPHA-D)-OH

Chemical Property:

• Melting Point: 178-183°C
• Boiling Point: 857.074 °C at 760 mmHg
• PKA: 3.32±0.10(Predicted)
• Flash Point: 472.142 °C
• PSA: 202.09000
• Density: 1.38 g/cm³
• LogP: 2.82130
• Storage Temp.: -15°C

Purity/Quality:

98%, ^*data from raw suppliers

2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-a-D-galactopyranosyl-Fmoc threonine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Fluorescently labeled glycopeptides containing GalNAcα1-O-Ser/Thr residues provide valuable immunology probes for the development of cancer vaccines.

Technology Process of FMOC-THR(GALNAC(AC)3-ALPHA-D)-OH

There total 62 articles about FMOC-THR(GALNAC(AC)3-ALPHA-D)-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%

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-(9H-fluoren-9-yl)methoxycarbonyl-O-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-threonine (116783-35-8)

Guidance literature:

With trifluoroacetic acid; In methoxybenzene;

DOI:10.1055/s-2003-42029

Reference yield: 97.0%

6-(3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(allyloxy)-4-oxobutan-2-yloxy)-5-acetamido-2-(acetoxymethyl)tetrahydro-2H-pyran-3,4-diyl diacetate (136497-89-7) → N-(9H-fluoren-9-yl)methoxycarbonyl-O-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-threonine (116783-35-8)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; N-methylaniline; In tetrahydrofuran; for 1h; Inert atmosphere;

DOI:10.1021/acs.orglett.5b00780

Reference yield: 94.0%

Nα-fluoren-9-ylmethoxycarbonyl-O-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-galactopyranosyl)-L-threoninebenzyl ester (100938-56-5) → N-(9H-fluoren-9-yl)methoxycarbonyl-O-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-threonine (116783-35-8)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethyl acetate; for 3h;

DOI:10.1039/c7ob02976d

upstream raw materials:

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

N^α-fluoren-9-ylmethoxycarbonyl-O-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-galactopyranosyl)-L-threoninebenzyl ester

acetic anhydride

6-(3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(allyloxy)-4-oxobutan-2-yloxy)-5-acetamido-2-(acetoxymethyl)tetrahydro-2H-pyran-3,4-diyl diacetate

Downstream raw materials:

dNBS-His-Gly-Val-(Ac3-Tn-α-Thr)-Ser-Ala-OH

dNBS-Gly-Val-(Ac3-Tn-α-Thr)-Ser-Ala-OH

C₃₈H₄₇N₃O₁₂

Refernces

• 1、 Heggemann, Carolin,Budke, Carsten,Schomburg, Benjamin,Majer, Zsuzsa,Wibrock, Marco,Koop, Thomas,Sewald, Norbert. "Antifreeze glycopeptide analogues: Microwave-enhanced synthesis and functional studies". . p. 213 - 222. Retrieved 2010.
• 2、 Lee, Dong Jun,Harris, Paul W.R.,Kowalczyk, Renata,Dunbar, P. Rod,Brimble, Margaret A.. "Microwave-assisted synthesis of fluorescein-labelled GalNAcα1-O-Ser/ Thr (Tn) glycopeptides as immunological probes". . p. 763 - 769. Retrieved 2010.
• 3、 Wu, Zhimeng,Guo, Xueqing,Guo, Zhongwu. "Chemoenzymatic synthesis of glycosylphosphatidylinositol-anchored glycopeptides". . p. 5773 - 5774. Retrieved 2010.
• 4、 Cao, Qi,Li, Bin,Liu, Jiazhi,Liu, Lizhen,Liu, Xinnan,Shao, Hong,Tao, Houchao,Wang, Can,Wang, Ping,Xue, Dongxiang,Ye, Farong,Yu, Biao,Zhao, Hongbo,Zhao, Jie. "Revealing Functional Significance of Interleukin-2 Glycoproteoforms Enabled by Expressed Serine Ligation". supporting information. . Retrieved 2022/01/31.
• 5、 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.