FMoc-D-Hyp(tBu)-OH

Base Information

• Chemical Name: FMoc-D-Hyp(tBu)-OH
• CAS No.: 268729-12-0
• Molecular Formula: C24H27NO5
• Molecular Weight: 409.47
• Mol file: 268729-12-0.mol

Synonyms:(2R,4S)-4-(1,1-Dimethylethoxy)-1,2-pyrrolidinedicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester;

Chemical Property of FMoc-D-Hyp(tBu)-OH

Chemical Property:

• Boiling Point: 578.6±50.0 °C(Predicted)
• PKA: 3.71±0.40(Predicted)
• PSA: 76.07000
• Density: 1.28±0.1 g/cm3(Predicted)
• LogP: 4.21600
• Storage Temp.: 2-8°C

Purity/Quality:

98.5% ^*data from raw suppliers

Fmoc-O-tert-butyl-D-trans-4-hydroxyproline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Fmoc-D-Hyp(tBu)-OH is used in the preparation of KMI-008 peptide derivatives and proline-based peptidomimetic analogs used as BACE1 inhibitors (β-secretase inhibitors).

Technology Process of FMoc-D-Hyp(tBu)-OH

There total 15 articles about FMoc-D-Hyp(tBu)-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: 95.0%

N-(9-fluorenylmethoxycarbonyl)-(2S,4S)-4-tert-butoxyproline benzyl ester (1239474-21-5) → N-(9-fluorenylmethoxycarbonyl)-(2S,4S)-4-tert-butoxyproline (268729-12-0)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; for 0.75h;

DOI:10.1021/ja103082y

Reference yield: 81.0%

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + 4S-O4(t-butyl)-D-Pro acid (79775-07-8,81806-53-3) → 4S-O4(t-butyl)-N1-(fluorenylmethyloxycarbonyl)-D-proline (268729-12-0)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; water; at 0 - 20 ℃; for 22h; pH=10;

DOI:10.1002/pep2.24140

Reference yield: 78.0%

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + C18H25NO5 → N-(9-fluorenylmethoxycarbonyl)-(2S,4S)-4-tert-butoxyproline (268729-12-0)

Guidance literature:

C₁₈H₂₅NO₅; With sodium hydroxide; In tetrahydrofuran;

With palladium on activated charcoal; hydrogen; In methanol;

(fluorenylmethoxy)carbonyl chloride; With sodium carbonate; In 1,4-dioxane; water;

DOI:10.1002/bip.22981

upstream raw materials:

(2R,4R)-1-benzyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate

(4S)-1-[(benzyloxy)carbonyl]-4-hydroxy-D-proline

(2R,4S)-1-benzyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate

cis-hydroxy-D-proline

Refernces

• 1、 Ganesh, Krishna N,More, Shahaji H. "Spiegelmeric 4R/S-hydroxy/amino-L/D-prolyl collagen peptides: conformation and morphology of self-assembled structures". . . Retrieved 2020/03/11.
• 2、 Shoulders, Matthew D.,Kotch, Frank W.,Choudhary, Amit,Guzei, Ilia A.,Raines, Ronald T.. "The aberrance of the 4 S diastereomer of 4-hydroxyproline". experimental part. p. 10857 - 10865. Retrieved 2010/09/17.