Fmoc-Ser(Ac)-OH

Base Information

• Chemical Name: Fmoc-Ser(Ac)-OH
• CAS No.: 171778-17-9
• Molecular Formula: C20H19 N O6
• Molecular Weight: 369.374
• DSSTox Substance ID: DTXSID20427038
• Nikkaji Number: J2.476.291B
• Wikidata: Q72435185
• Mol file: 171778-17-9.mol

Synonyms:Fmoc-Ser(Ac)-OH;171778-17-9;Fmoc-L-Ser(Ac);(2S)-3-acetyloxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic Acid;fmoc-O-acetylserine;DTXSID20427038;HSGIKRPBGCJRDB-SFHVURJKSA-N;AMY39940;MFCD00077070;NSC778228;AKOS025289449;DS-7550;HY-W048674;NSC 778228;NSC-778228;CS-0100968;F10690;A921678;N-(9H-Fluorene-9-ylmethoxycarbonyl)-O-acetyl-L-serine;N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-O-acetyl-L-serine;(S)-3-((9H-Fluoren-9-yl)methoxy)-2-(acetoxymethyl)-2-amino-3-oxopropanoic acid

Chemical Property of Fmoc-Ser(Ac)-OH

Chemical Property:

• Boiling Point: 611.2±55.0 °C(Predicted)
• PKA: 3.27±0.10(Predicted)
• PSA: 101.93000
• Density: 1.322
• LogP: 2.93230
• Storage Temp.: 2-8°C
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 369.12123733
• Heavy Atom Count: 27
• Complexity: 543

Purity/Quality:

98%,99%, ^*data from raw suppliers

Fmoc-O-acetyl-L-serine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Fmoc-Ser(Ac)-OH

There total 2 articles about Fmoc-Ser(Ac)-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: 74.52%

O-acetyl-L-serine (5147-00-2,25248-96-8,44901-25-9) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → Nα-(9-fluorenylmethoxycarbonyl)-O-acetyl-L-serine (171778-17-9,608512-87-4)

Guidance literature:

With hydrogenchloride; sodium carbonate; In water; ethyl acetate; at 20 - 30 ℃;

Reference yield: 48.0%

1,3,4,6-tetra-O-acetyl-2-deoxy-2-fluoro-β-D-glucopyranose (31077-89-1) + N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine (73724-45-5) → Nα-(9-fluorenylmethoxycarbonyl)-O-acetyl-L-serine (171778-17-9,608512-87-4)

Guidance literature:

With boron trifluoride diethyl etherate; In acetonitrile; at 20 ℃; for 24h;

DOI:10.1002/jlcr.963

Reference yield: 93.0%

3-amino-deoxycombretastatin A4 (162705-07-9) + Nα-(9-fluorenylmethoxycarbonyl)-O-acetyl-L-serine (171778-17-9,608512-87-4) → (S,Z)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-((2-methoxy-5-(3,4,5-trimethoxystyryl)phenyl)amino)-3-oxopropyl acetate (286463-65-8)

Guidance literature:

With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In dichloromethane; at 20 ℃; for 16h; Inert atmosphere;

DOI:10.1016/j.bmc.2016.01.007

upstream raw materials:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-fluoro-β-D-glucopyranose

N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine

O-acetyl-L-serine

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

Downstream raw materials:

(S,Z)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-((2-methoxy-5-(3,4,5-trimethoxystyryl)phenyl)amino)-3-oxopropyl acetate

(S,Z)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-((5-methoxy-2-(3,4,5-trimethoxystyryl)phenyl)amino)-3-oxopropyl acetate

(Z)-1-(3,4,5-trimethoxphenyl)-2-(3'-amino-4'-difluoromethoxyphenyl)-ethene-3'-N-serinamide

C₅₈H₅₆N₄O₁₄

Refernces

• 1、 Maschauer, Simone,Pischetsrieder, Monika,Kuwert, Torsten,Prante, Olaf. "Utility of 1,3,4,6-tetra-O-acetyl-2-deoxy-2-[18F] fluoroglucopyranoside for no-carrier-added18F-glycosylation of amino acids". . p. 701 - 719. Retrieved 2007/10/03.