N-Fmoc-(S)-2-pentylglycine

Base Information

• Chemical Name: N-Fmoc-(S)-2-pentylglycine
• CAS No.: 1197020-22-6
• Molecular Formula: C₂₂H₂₅NO₄
• Molecular Weight: 367.445
• Mol file: 1197020-22-6.mol

Synonyms:(S)-2-{[((9H-Fluoren-9-yl)methoxy)carbonyl]amino}heptanoic acid

Chemical Property of N-Fmoc-(S)-2-pentylglycine

Chemical Property:

• Boiling Point: 573.7±33.0 °C(Predicted)
• PKA: 3.91±0.21(Predicted)
• Density: 1.190±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C

Purity/Quality:

≥98%, ^*data from raw suppliers

N-Fmoc-S-2-amino-Heptanoic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-Fmoc-(S)-2-pentylglycine

There total 5 articles about N-Fmoc-(S)-2-pentylglycine 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: 78.0%

(2S)-2-aminoheptanoic acid (44902-02-5) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → (S)-2-{[((9H-Fluoren-9-yl)methoxy)carbonyl]amino}heptanoic acid (1197020-22-6,1219184-45-8)

Guidance literature:

(2S)-2-aminoheptanoic acid; N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide; With sodium carbonate; In 1,4-dioxane; water; for 16h;

With hydrogenchloride; In water; pH=2;

DOI:10.1021/ol3023853

Reference yield:

C22H23NO4 → (S)-2-{[((9H-Fluoren-9-yl)methoxy)carbonyl]amino}heptanoic acid (1197020-22-6,1219184-45-8)

Guidance literature:

With hydrogen; In methanol; at 20 ℃; under 3102.97 Torr;

DOI:10.1002/psc.2522

Reference yield:

2-(9H-fluoren-9-ylmethoxycarbonylamino)-pent-4-enoic acid (146549-21-5) → (S)-2-{[((9H-Fluoren-9-yl)methoxy)carbonyl]amino}heptanoic acid (1197020-22-6,1219184-45-8)

Guidance literature:

Multi-step reaction with 2 steps

1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 20 °C / Inert atmosphere; Schlenk technique

2: hydrogen / methanol / 20 °C / 3102.97 Torr

With Hoveyda-Grubbs catalyst second generation; hydrogen; In methanol; dichloromethane;

DOI:10.1002/psc.2522

upstream raw materials:

(2S)-2-aminoheptanoic acid

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

2-(9H-fluoren-9-ylmethoxycarbonylamino)-pent-4-enoic acid

2-aminoheptanoic acid

Downstream raw materials:

cyclo-[Asn-Pro-(L-2-aminoheptanoyl)-Phe-Gly-Asn-Leu]

Refernces

• 1、 Wang, Zhen J.,Spiccia, Nicolas D.,Jackson, W. Roy,Robinson, Andrea J.. "Tandem Ru-alkylidene-catalysed cross metathesis/hydrogenation: Synthesis of lipophilic amino acids". . p. 470 - 476. Retrieved 2013.
• 2、 Erdbrink, Holger,Nyakatura, Elisabeth K.,Huhmann, Susanne,Gerling, Ulla I.M.,Lentz, Dieter,Koksch, Beate,Czekelius, Constantin. "Synthesis of enantiomerically pure (2S,3S)-5,5,5-trifluoroisoleucine and (2R,3S)-5,5,5-trifluoro-allo-isoleucine". supporting information. p. 2009 - 2014. Retrieved 2013/11/06.