FMoc-α-Me-Lys(Boc)-OH

Base Information

• Chemical Name: FMoc-α-Me-Lys(Boc)-OH
• CAS No.: 1202003-49-3
• Molecular Formula: C27H34N2O6
• Molecular Weight: 482.577
• Mol file: 1202003-49-3.mol

Synonyms:(S)-Na-Fmoc-NW-Boc-α-Methyllysine;Fmoc-alpha-Me-L-Lys(Boc)-OH;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-6-((tert-butoxycarbonyl)amino)-2-methylhexanoic acid;N6-[(1,1-Dimethylethoxy)carbonyl]-N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-2-methyl-L-lysine

Chemical Property of FMoc-α-Me-Lys(Boc)-OH

Chemical Property:

• Boiling Point: 687.9±55.0 °C(Predicted)
• PKA: 3.92±0.41(Predicted)
• PSA: 120.94000
• Density: 1.196±0.06 g/cm3(Predicted)
• LogP: 5.47220
• Storage Temp.: 2-8°C

Purity/Quality:

≥98%, ^*data from raw suppliers

(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-6-((tert-butoxycarbonyl)amino)-2-methylhexanoicAcid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 36/37/38-40-67
• Safety Statements: 23-24/25-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-6-((tert-butoxycarbonyl)amino)-2-methylhexanoic acid is a reagent in the preparation/biological evaluation of a vapreotide analogs containing (S)?-?α-?methyl-?lysine. (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-6-((tert-butoxycarbonyl)amino)-2-methylhexanoic acid is a reagent in the preparation/biological evaluation of a vapreotide analogs containing (S)-α-methyl-lysine.

Technology Process of FMoc-α-Me-Lys(Boc)-OH

There total 9 articles about FMoc-α-Me-Lys(Boc)-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: 94.0%

di-tert-butyl dicarbonate (24424-99-5) + fluorenylmethyloxycarbonylamino-2-methylhexanoic acid hydrochloride (1453178-51-2) → (S)-tBoc-Fmoc-α-methyl-α-lysine-OH (1202003-49-3)

Guidance literature:

With sodium hydrogencarbonate; In 1,4-dioxane; water; at 0 ℃; for 0.333333h;

DOI:10.1039/c3ob41282b

Reference yield:

(L)-α-Me-Lys(Boc)-OH (1202003-44-8) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → (S)-tBoc-Fmoc-α-methyl-α-lysine-OH (1202003-49-3)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; water; at 20 ℃;

DOI:10.1016/j.tetlet.2009.09.148

Reference yield:

Diethyl 2-(N-butylphthalimido)-2-methylmalonate (17377-68-3) → (S)-tBoc-Fmoc-α-methyl-α-lysine-OH (1202003-49-3)

Guidance literature:

Multi-step reaction with 5 steps

1: pig liver esterase / aq. phosphate buffer; ethanol / pH 7.4 / Enzymatic reaction

2: triethylamine; diphenyl phosphoryl azide / 1,2-dichloro-ethane / 5 h / 20 °C / Inert atmosphere; Reflux

3: titanium(IV) isopropylate / toluene / 12 h / 80 °C / Inert atmosphere

4: hydrogenchloride / water; 1,4-dioxane / 24 h / Reflux

5: sodium hydrogencarbonate / water; 1,4-dioxane / 0.33 h / 0 °C

With titanium(IV) isopropylate; hydrogenchloride; pig liver esterase; diphenyl phosphoryl azide; sodium hydrogencarbonate; triethylamine; In 1,4-dioxane; aq. phosphate buffer; ethanol; water; 1,2-dichloro-ethane; toluene; 2: |Curtius Rearrangement;

DOI:10.1039/c3ob41282b

upstream raw materials:

di-tert-butyl dicarbonate

(L)-Fmoc-α-Me-Lys-OH

(L)-α-Me-Lys(Boc)-OH

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

Refernces

• 1、 Banerjee, Souvik,Wiggins, Walker J.,Geoghegan, Jessie L.,Anthony, Catherine T.,Woltering, Eugene A.,Masterson, Douglas S.. "Novel synthesis of various orthogonally protected Cα- methyllysine analogues and biological evaluation of a Vapreotide analogue containing (S)-α-methyllysine". . p. 6307 - 6319. Retrieved 2013/09/23.