(2S,3R)-Benzyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-hydroxybutanoate

Base Information

• Chemical Name: (2S,3R)-Benzyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-hydroxybutanoate
• CAS No.: 73724-48-8
• Molecular Formula: C26H25 N O5
• Molecular Weight: 431.488
• DSSTox Substance ID: DTXSID80449438
• Nikkaji Number: J1.158.085H
• Mol file: 73724-48-8.mol

Synonyms:73724-48-8;Fmoc-Thr-Obzl;(2S,3R)-Benzyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-hydroxybutanoate;benzyl (2S,3R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hydroxybutanoate;(2S,3R)-Benzyl 2-(((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-hydroxybutanoate;L-Threonine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-, phenylmethyl ester;SCHEMBL13694941;SCHEMBL13695275;DTXSID80449438;MFCD11505901;AKOS016009028;DS-4328;CS-0158246;D82388;N-(9-fluorenylmeth-oxycarbonyl)-l-threonine benzyl ester;N-(9H-Fluorene-9-ylmethoxycarbonyl)threonine benzyl ester;(2S,3R)-Benzyl2-(((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-hydroxybutanoate;benzyl (2S,3R)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-hydroxybutanoate;N-alpha-(9-Fluorenylmethyloxycarbonyl)-L-threonine benZyl ester (Fmoc-L-Thr-OBZl)

Chemical Property of (2S,3R)-Benzyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-hydroxybutanoate

Chemical Property:

• Boiling Point: 656.9±55.0 °C(Predicted)
• PKA: 10.34±0.46(Predicted)
• Density: 1.257±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 431.17327290
• Heavy Atom Count: 32
• Complexity: 612

Purity/Quality:

95+% ^*data from raw suppliers

Fmoc-Thr(Bzl)-OH ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(C(=O)OCC1=CC=CC=C1)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24)O
• Isomeric SMILES: C[C@H]([C@@H](C(=O)OCC1=CC=CC=C1)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24)O

Technology Process of (2S,3R)-Benzyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-hydroxybutanoate

There total 5 articles about (2S,3R)-Benzyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-hydroxybutanoate 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: 91.0%

benzyl bromide (100-39-0) + Fmoc-Thr-OH (73731-37-0) → N-(fluoren-9-ylmethoxycarbonyl)-L-threonine benzyl ester (73724-48-8)

Guidance literature:

Fmoc-Thr-OH; With caesium carbonate; In methanol; for 0.25h; Inert atmosphere;

benzyl bromide; In N,N-dimethyl-formamide; at 20 ℃; Inert atmosphere;

DOI:10.1016/j.tet.2011.10.099

Reference yield: 87.0%

((9-fluorenylmethyl)oxy)carbonyl chloroformate (86088-58-6) + L-threonine benzyl ester oxalate salt (201274-07-9) → N-(fluoren-9-ylmethoxycarbonyl)-L-threonine benzyl ester (73724-48-8)

Guidance literature:

With sodium hydrogencarbonate; In 1,4-dioxane; for 24h;

DOI:10.1021/jo00163a027

Reference yield: 85.0%

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + L-threonine benzyl ester hydrochloride → N-(fluoren-9-ylmethoxycarbonyl)-L-threonine benzyl ester (73724-48-8)

Guidance literature:

With N,N-diethyl-N-isopropylamine; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1021/jo005712m

upstream raw materials:

((9-fluorenylmethyl)oxy)carbonyl chloroformate

L-threonine benzyl ester oxalate salt

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

L-threonine benzyl ester hemioxalate

Downstream raw materials:

N^α-fluoren-9-ylmethoxycarbonyl-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-L-threonine benzyl ester

N^α-fluoren-9-ylmethoxycarbonyl-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-L-threonine benzyl ester

N-(9-fluorenylmethoxycarbonyl)-O-(2-azido-4,6-O-benzylidene-3-O-(2-chloroacetyl)-2-deoxy-α-D-galactopyranosyl)-L-threonine benzyl ester

N^α-fluoren-9-ylmethoxycarbonyl-O-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-L-threonine benzylester

Refernces

• 1、 Leiria Campo, Vanessa,Riul, Thalita B.,Oliveira Bortot, Leandro,Martins-Teixeira, Maristela B.,Fiori Marchiori, Marcelo,Iaccarino, Emanuela,Ruvo, Menotti,Dias-Baruffi, Marcelo,Carvalho, Ivone. "A Synthetic MUC1 Glycopeptide Bearing βGalNAc-Thr as a Tn Antigen Isomer Induces the Production of Antibodies against Tumor Cells". . p. 527 - 538. Retrieved 2017/03/22.
• 2、 Loke, Inga,Park, Natja,Kempf, Karl,Jagusch, Carsten,Schobert, Rainer,Laschat, Sabine. "Influence of steric parameters on the synthesis of tetramates from α-amino-β-alkoxy-esters and Ph3PCCO". supporting information; experimental part. p. 697 - 704. Retrieved 2012/01/05.