(S)-2-(((9H-FLUOREN-9-YL)METHOXY)CARBONYLAMINO)-2-METHYLHEPT-6-ENOIC ACID

Base Information

• Chemical Name: (S)-2-(((9H-FLUOREN-9-YL)METHOXY)CARBONYLAMINO)-2-METHYLHEPT-6-ENOIC ACID
• CAS No.: 288617-73-2
• Molecular Formula: C23H25NO4
• Molecular Weight: 379.45
• Hs Code.: 2924299090
• Mol file: 288617-73-2.mol

Synonyms:(S)-N-Fmoc-2-(4'-pentenyl)alanine;

Chemical Property of (S)-2-(((9H-FLUOREN-9-YL)METHOXY)CARBONYLAMINO)-2-METHYLHEPT-6-ENOIC ACID

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.582
• Boiling Point: 591.736 °C at 760 mmHg
• PKA: 3.91±0.41(Predicted)
• Flash Point: 311.671 °C
• PSA: 75.63000
• Density: 1.186 g/cm³
• LogP: 5.11560
• Storage Temp.: ?20°C

Purity/Quality:

98% ^*data from raw suppliers

Fmoc-(S)-2-(4-pentenyl)Ala-OH ≥97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N
• Hazard Codes: N
• Statements: 50
• Safety Statements: 61

MSDS Files:

SDS file from LookChem

Useful:

• Description: (S)-2-(((9H-FLUOREN-9-YL)METHOXY)CARBONYLAMINO)-2-METHYLHEPT-6-ENOIC ACID is a product used for preparing stapled peptides by ring closing metathesis.
• Uses: Fmoc-(S)-2-(4-pentenyl)Ala-OH is a Fmoc-protected amino acid that can be used to create peptide libraries.

Technology Process of (S)-2-(((9H-FLUOREN-9-YL)METHOXY)CARBONYLAMINO)-2-METHYLHEPT-6-ENOIC ACID

There total 20 articles about (S)-2-(((9H-FLUOREN-9-YL)METHOXY)CARBONYLAMINO)-2-METHYLHEPT-6-ENOIC 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: 84.0%

(+)-(S)-2-amino-2-methylhept-6-enoic acid (1011309-61-7,1824552-06-8) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-methylhept-6-enoic acid (288617-73-2,288617-77-6)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; water; at 0 - 20 ℃;

DOI:10.1016/j.tet.2019.130485

Reference yield: 76.0%

(S)-2-amino-2-methyl-hept-6-enoic acid hydrochloride (1370371-77-9) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-methylhept-6-enoic acid (288617-73-2,288617-77-6)

Guidance literature:

With sodium carbonate; In tetrahydrofuran; water; at 20 - 25 ℃; pH=8.5 - 9;

Reference yield: 62.0%

(S)-2-(tert-butoxycarbonyl)amino-2-methylhept-6-enoic acid (1263048-46-9) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-methylhept-6-enoic acid (288617-73-2,288617-77-6)

Guidance literature:

(S)-2-(tert-butoxycarbonyl)amino-2-methylhept-6-enoic acid; With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 0.5h;

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide; With sodium carbonate; In water; acetone; at 0 ℃; for 1h;

With hydrogenchloride; In water; acetone; pH=3;

DOI:10.1039/c3cc45231j

upstream raw materials:

9-fluorenylmethyl carbamate

1-iodo-4-pentene

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

(R)-2-amino-2-methylhept-6-enoic acid

Downstream raw materials:

C₇₈H₁₁₈N₁₈O₁₄

C₇₇H₁₁₆N₁₈O₁₃

C₇₅H₁₁₀N₁₄O₁₄

Refernces

• 1、 Li, Bo,Zhang, Jie,Xu, Yongjuan,Yang, Xiaoxiao,Li, Li. "Improved synthesis of unnatural amino acids for peptide stapling". supporting information. p. 2374 - 2377. Retrieved 2017/05/29.
• 2、 -. "STITCHED POLYPEPTIDES". . . Retrieved 2017/01/02.