BOC-(2S,3RS)-2-AMINO-3-HYDROXY-4-METHYLPENTANOIC ACID

Base Information

• Chemical Name: BOC-(2S,3RS)-2-AMINO-3-HYDROXY-4-METHYLPENTANOIC ACID
• CAS No.: 1217531-78-6
• Molecular Formula: C₁₁H₂₁NO₅
• Molecular Weight: 247.291
• Mol file: 1217531-78-6.mol

Synonyms:

Chemical Property of BOC-(2S,3RS)-2-AMINO-3-HYDROXY-4-METHYLPENTANOIC ACID

Chemical Property:

Purity/Quality:

98%min ^*data from raw suppliers

Boc-(2S,3rS)-2-amino-3-hydroxy-4-methylpentanoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of BOC-(2S,3RS)-2-AMINO-3-HYDROXY-4-METHYLPENTANOIC ACID

There total 20 articles about BOC-(2S,3RS)-2-AMINO-3-HYDROXY-4-METHYLPENTANOIC 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: 71.0%

(2S,3R)-3-hydroxyleucine (5817-22-1,6645-45-0,10148-70-6,28908-11-4,35016-54-7,35016-62-7,87421-23-6,87421-24-7,10148-71-7) + di-tert-butyl dicarbonate (24424-99-5) → (2S,3R)-2-((tert-butoxycarbonyl)amino)-3-hydroxy-4-methylpentanoic acid (1217531-78-6,929198-84-5,102507-17-5)

Guidance literature:

(2S,3R)-3-hydroxyleucine; With lithium hydroxide; In 1,4-dioxane; water; at 20 ℃; for 0.166667h;

di-tert-butyl dicarbonate; In 1,4-dioxane; water; at 20 ℃; for 2h;

DOI:10.1016/j.bmc.2018.12.002

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) + (2R,3R)-N-benzyl-3-hydroxyleucine → N-tert-butoxycarbonyl-β-(R)-hydroxy-D-leucine (1217531-78-6,929198-84-5,102507-17-5)

Guidance literature:

(2R,3R)-N-benzyl-3-hydroxyleucine; With 20 % Pd(OH)2/C; hydrogen; sodium hydroxide; In methanol; for 8h;

di-tert-butyl dicarbonate; With sodium hydroxide; In methanol; Inert atmosphere;

With potassium hydrogensulfate; In water; pH=3;

DOI:10.1016/j.bmc.2011.05.022

Reference yield:

C11H23NO4 → N-tert-butoxycarbonyl-β-(S)-hydroxy-D-leucine (1217531-78-6,929198-84-5,102507-17-5)

Guidance literature:

With sodium chlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; In aq. phosphate buffer; acetonitrile; at 35 ℃; for 3h; pH=6.7; Inert atmosphere;

DOI:10.1039/c5cc08324a

upstream raw materials:

(2SR,3RS)-2-amino-3-hydroxy-4-methylpentanoic acid

di-tert-butyl dicarbonate

ethyl 2-(tert-butoxycarbonylamino)-3-hydroxy-4-methyl-pentanoate

ethyl (2RS)-2-(dibenzylamino)-4-methyl-3-oxopentanoate

Downstream raw materials:

(2R,3S)-2-amino-3-hydroxy-4-methylpentanoic acid

C₂₁H₂₃NO₅

Refernces

• 1、 Giltrap, Andrew M.,Haeckl, F. P. Jake,Kurita, Kenji L.,Linington, Roger G.,Payne, Richard J.. "Synthetic Studies Toward the Skyllamycins: Total Synthesis and Generation of Simplified Analogues". . p. 7250 - 7270. Retrieved 2018/06/01.
• 2、 Liu, Junyang,Wang, Lei,Zhang, Juefei,Xu, Zhengshuang,Ye, Tao. "The total synthesis and stereochemical assignment of scytonemin A". . p. 1002 - 1005. Retrieved 2016/01/16.