Fmoc-Threoninol

Base Information

• Chemical Name: Fmoc-Threoninol
• CAS No.: 176380-53-3
• Molecular Formula: C19H21NO4
• Molecular Weight: 327.38
• DSSTox Substance ID: DTXSID40427237
• Nikkaji Number: J1.635.122I
• Wikidata: Q72478971
• Mol file: 176380-53-3.mol

Synonyms:Fmoc-Threoninol;176380-53-3;N-Fmoc-L-threonol;Fmoc-L-threoninol;(9H-Fluoren-9-yl)methyl ((2R,3R)-1,3-dihydroxybutan-2-yl)carbamate;(1R,2R)-(2-Hydroxy-1-hydroxymethylpropyl)carbamic acid 9H-fluoren-9-ylmethyl ester;9H-fluoren-9-ylmethyl N-[(2R,3R)-1,3-dihydroxybutan-2-yl]carbamate;Fmoc-Thr-ol;n-fmoc-l-threoninol;9-Fluorenylmethyloxycarbonyl-L-threoninol;n-(9-fluorenylmethoxycarbonyl)-threoninol;SCHEMBL20371129;DTXSID40427237;AMY22755;MFCD00270218;AKOS015908605;CS-W009863;(1R,2R)-(2-Hydroxy-1-hydroxymethyl-propyl)-carbamic acid 9H-fluoren-9-ylmethyl ester;Carbamic acid, N-[(1R,2R)-2-hydroxy-1-(hydroxymethyl)propyl]-, 9H-fluoren-9-ylmethyl ester;DS-13862;A26874;J-011184;9H-Fluoren-9-ylmethyl [(2R,3R)-1,3-dihydroxybutan-2-yl]carbamate;[(1R,2R)-1-(Hydroxymethyl)-2-hydroxypropyl]carbamic acid 9H-fluorene-9-ylmethyl ester;(1R pound not2R)-(2-Hydroxy-1-hydroxymethyl-propyl)-carbamic acid 9H-fluoren-9-ylmethyl ester

Chemical Property of Fmoc-Threoninol

Chemical Property:

• Vapor Pressure: 1.35E-14mmHg at 25°C
• Refractive Index: 1.608
• Boiling Point: 586.5 °C at 760 mmHg
• PKA: 11.27±0.46(Predicted)
• Flash Point: 308.5 °C
• PSA: 78.79000
• Density: 1.259 g/cm³
• LogP: 2.65770
• Storage Temp.: -15°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 327.14705815
• Heavy Atom Count: 24
• Complexity: 408

Purity/Quality:

97% ^*data from raw suppliers

Fmoc-L-threoninol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(CO)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13)O
• Isomeric SMILES: C[C@H]([C@@H](CO)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13)O

Technology Process of Fmoc-Threoninol

There total 2 articles about Fmoc-Threoninol 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: 80.0%

(2R,3R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-1-O-(tert-butyldimethylsilyl)butane-1,3-diol (377082-52-5) → (2R,3R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)butane-1,3-diol (176380-53-3,252049-02-8)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1021/jo015844v

Reference yield: 80.0%

Fmoc-Thr-OH (73731-37-0) → (2R,3R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)butane-1,3-diol (176380-53-3,252049-02-8)

Guidance literature:

With borane-THF; In tetrahydrofuran; at 20 ℃; for 8h;

DOI:10.1016/S0968-0896(99)00125-X

Reference yield: 100.0%

benzaldehyde dimethyl acetal (1125-88-8) + (2R,3R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)butane-1,3-diol (176380-53-3,252049-02-8) → (9H-fluoren-9-yl)methyl ((4R,5R)-4-methyl-2-phenyl-1,3-dioxan-5-yl)carbamate

Guidance literature:

With (1S)-10-camphorsulfonic acid; In acetonitrile; for 4h; Reflux;

DOI:10.1021/acs.bioconjchem.8b00365

upstream raw materials:

Fmoc-Thr-OH

(2R,3R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-1-O-(tert-butyldimethylsilyl)butane-1,3-diol

Downstream raw materials:

N-fluorenyl-9-ylmethoxycarbonyl-L-threoninol p-carboxybenzacetal

Fmoc-Thr-OH