(2S,3R)-2-((((9H-Fluoren-9-yl)Methoxy)carbonyl)aMino)-3-acetoxybutanoic acid

Base Information

• Chemical Name: (2S,3R)-2-((((9H-Fluoren-9-yl)Methoxy)carbonyl)aMino)-3-acetoxybutanoic acid
• CAS No.: 181817-14-1
• Molecular Formula: C21H21NO6
• Molecular Weight: 383.39454
• DSSTox Substance ID: DTXSID80587844
• Nikkaji Number: J2.476.288B
• Wikidata: Q82480332
• Mol file: 181817-14-1.mol

Synonyms:(2S,3R)-2-((((9H-Fluoren-9-yl)Methoxy)carbonyl)aMino)-3-acetoxybutanoic acid;O-Acetyl-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-threonine

Chemical Property of (2S,3R)-2-((((9H-Fluoren-9-yl)Methoxy)carbonyl)aMino)-3-acetoxybutanoic acid

Chemical Property:

• PSA: 105.42000
• LogP: 3.13430
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 383.13688739
• Heavy Atom Count: 28
• Complexity: 571

Purity/Quality:

>98% ^*data from raw suppliers

Fmoc-O-acetyl-L-threonine,99%(HPLC) 99%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of (2S,3R)-2-((((9H-Fluoren-9-yl)Methoxy)carbonyl)aMino)-3-acetoxybutanoic acid

There total 2 articles about (2S,3R)-2-((((9H-Fluoren-9-yl)Methoxy)carbonyl)aMino)-3-acetoxybutanoic acid 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: 48.0%

1,3,4,6-tetra-O-acetyl-2-deoxy-2-fluoro-β-D-glucopyranose (31077-89-1) + Fmoc-Thr-OH (73731-37-0) → Nα-(9-fluorenylmethoxycarbonyl)-O-acetyl-L-threonine (181817-14-1) + Nα-(9-fluorenylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-D-glucopyranosyl)-L-threonine + Nα-(9-fluorenylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-D-glucopyranosyl)-L-threonine

Guidance literature:

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

DOI:10.1002/jlcr.963

Reference yield:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + O-acetyl-L-threonine (17012-42-9) → Nα-(9-fluorenylmethoxycarbonyl)-O-acetyl-L-threonine (181817-14-1)

Guidance literature:

With triethylamine; In tetrahydrofuran; 1,4-dioxane; at 20 ℃; for 12h;

DOI:10.1016/j.tet.2015.05.116

Reference yield: 94.0%

Nα-(9-fluorenylmethoxycarbonyl)-O-acetyl-L-threonine (181817-14-1) → O-acetyl-L-threonine (17012-42-9)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 50 ℃; for 3h;

DOI:10.1007/s00726-013-1625-7

upstream raw materials:

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

Fmoc-Thr-OH

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

O-acetyl-L-threonine

Downstream raw materials:

O-acetyl-L-threonine

N-Fmoc-N-methyl-L-threonine

(2S,3R)-benzyl 2-methylamino-3-((triisopropylsilyl)oxy)butanoate

(5S)-4-(benzyloxy)-1-methyl-5-{(1R)-1-[(triisopropylsilyl)oxy]ethyl}-1H-pyrrol-2(5H)-one

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