FMOC-L-LEUCINOL

Base Information

• Chemical Name: FMOC-L-LEUCINOL
• CAS No.: 139551-83-0
• Molecular Formula: C21H25NO3
• Molecular Weight: 339.434
• Hs Code.: 2924299090
• Mol file: 139551-83-0.mol

Synonyms:Carbamicacid, [(1S)-1-(hydroxymethyl)-3-methylbutyl]-, 9H-fluoren-9-ylmethyl ester(9CI);Carbamic acid, [1-(hydroxymethyl)-3-methylbutyl]-, 9H-fluoren-9-ylmethylester, (S)-;NPC 15427;

Chemical Property of FMOC-L-LEUCINOL

Chemical Property:

• Melting Point: 112-113 °C
• Boiling Point: 525.2 °C at 760 mmHg
• PKA: 11.48±0.46(Predicted)
• Flash Point: 271.4 °C
• PSA: 58.56000
• Density: 1.148 g/cm³
• LogP: 4.32300
• Storage Temp.: -15°C

Purity/Quality:

99% ^*data from raw suppliers

Fmoc-L-leucinol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Fmoc-L-leucinol is an intermediate used in the preparation of Fmoc-protected amino azides from Fmoc-protected amino alcohols.

Technology Process of FMOC-L-LEUCINOL

There total 15 articles about FMOC-L-LEUCINOL 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: 95.0%

Fmoc-Leu-OH (35661-60-0) → (S)-(9H-fluoren-9-yl)methyl (1-hydroxy-4-methylpentan-2-yl)carbamate (139551-83-0,215178-41-9)

Guidance literature:

Fmoc-Leu-OH; With 4-methyl-morpholine; In 1,2-dimethoxyethane; at -15 ℃; for 1h;

With sodium tetrahydroborate; In 1,2-dimethoxyethane; water; at -15 ℃; Further stages.;

DOI:10.1021/jo010656q

Reference yield: 95.0%

N-(9-fluorenylmethoxycarbonyl)-L-leucine pentafluorophenyl ester (86060-88-0) → (S)-(9H-fluoren-9-yl)methyl (1-hydroxy-4-methylpentan-2-yl)carbamate (139551-83-0,215178-41-9)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; at 20 ℃; for 0.25h;

DOI:10.1016/j.tetlet.2007.09.124

Reference yield: 94.0%

(S)-2-amino-4-methylpentan-1-ol (7533-40-6,14438-11-0) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → (S)-(9H-fluoren-9-yl)methyl (1-hydroxy-4-methylpentan-2-yl)carbamate (139551-83-0,215178-41-9)

Guidance literature:

With sodium carbonate; In tetrahydrofuran; for 2h; pH 9;

DOI:10.1016/0040-4020(95)00778-7

upstream raw materials:

(S)-4-Isobutyl-2,5-dioxo-oxazolidine-3-carboxylic acid 9H-fluoren-9-ylmethyl ester

(S)-2-amino-4-methylpentan-1-ol

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

N-(fluorenylmethyloxycarbonyl)-L-leucinal

Downstream raw materials:

3-(3-((S)-2-acetylamino-4-methylpentylamino)phenyl)-2H-chromen-2-one

C₆₇H₈₃N₇O₁₁

3-(3-((S)-2-amino-4-methylpentylamino)phenyl)-2H-chromen-2-one

Refernces

• 1、 Chen, Ying-Ying,Chang, Li-Te,Chen, Hung-Wei,Yang, Chia-Ying,Hsin, Ling-Wei. "Fast and Facile Synthesis of 4-Nitrophenyl 2-Azidoethylcarbamate Derivatives from N-Fmoc-Protected α-Amino Acids as Activated Building Blocks for Urea Moiety-Containing Compound Library". . p. 131 - 136. Retrieved 2017/04/24.
• 2、 Bockus, Andrew T.,Lexa, Katrina W.,Pye, Cameron R.,Kalgutkar, Amit S.,Gardner, Jarret W.,Hund, Kathryn C.R.,Hewitt, William M.,Schwochert, Joshua A.,Glassey, Emerson,Price, David A.,Mathiowetz, Alan M.,Liras, Spiros,Jacobson, Matthew P.,Lokey, R. Scott. "Probing the Physicochemical Boundaries of Cell Permeability and Oral Bioavailability in Lipophilic Macrocycles Inspired by Natural Products". supporting information. p. 4581 - 4589. Retrieved 2015/06/25.