3-tert-butylsulfanyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid

Base Information

• Chemical Name: 3-tert-butylsulfanyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
• CAS No.: 67436-13-9
• Molecular Formula: C22H25NO4S
• Molecular Weight: 399.511
• Hs Code.: 2930 90 16
• NSC Number: 334299
• Mol file: 67436-13-9.mol

Synonyms:Fmoc-S-tert-butyl-Cys;N(alpha)-fluorenylmethyloxycarbonyl-S-tert-butylcysteine

Chemical Property of 3-tert-butylsulfanyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid

Chemical Property:

• Appearance/Colour: White to off white powder
• Vapor Pressure: 2.08E-15mmHg at 25°C
• Melting Point: 135-137 °C
• Refractive Index: 1.599
• Boiling Point: 603.4 °C at 760 mmHg
• PKA: 3.49±0.10(Predicted)
• Flash Point: 318.7 °C
• PSA: 100.93000
• Density: 1.237 g/cm³
• LogP: 4.90090
• Storage Temp.: 2-8°C
• Water Solubility.: Soluble in water
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 399.15042945
• Heavy Atom Count: 28
• Complexity: 539

Purity/Quality:

99% ^*data from raw suppliers

Fmoc-S-tert-butyl-L-cysteine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)SCC(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Uses: Fmoc-Cys(tBu)-OH, is an amino acid building block used in peptide synthesis. With a growing peptide drug market the fast, reliable synthesis of peptides is of great importance.

Technology Process of 3-tert-butylsulfanyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid

There total 4 articles about 3-tert-butylsulfanyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic 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: 79.0%

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + S-tert-Butyl-N-acetyl-L-cysteine hydrochloride (2481-09-6) → (R)-3-tert-Butylsulfanyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid (67436-13-9)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; water; for 1h;

Reference yield:

N,N'-bis[(9H-fluoren-9-ylmethoxy)carbonyl]-L-cystine (135273-01-7) → (R)-3-tert-Butylsulfanyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid (67436-13-9)

Guidance literature:

Multi-step reaction with 2 steps

1: zinc; hydrogenchloride / water; ethyl acetate

2: trifluoroacetic acid / 4 h

With hydrogenchloride; trifluoroacetic acid; zinc; In water; ethyl acetate;

Reference yield:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → (R)-3-tert-Butylsulfanyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid (67436-13-9)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium carbonate / acetone; water / 50 °C

2: zinc; hydrogenchloride / water; ethyl acetate

3: trifluoroacetic acid / 4 h

With hydrogenchloride; sodium carbonate; trifluoroacetic acid; zinc; In water; ethyl acetate; acetone;

upstream raw materials:

(fluorenylmethoxy)carbonyl chloride

S-tert-Butyl-N-acetyl-L-cysteine hydrochloride

N^α-fluoren-9-ylmethoxycarbonyl-L-cysteine

tert-butyl alcohol

Downstream raw materials:

Fmoc-Cys(tBu)-OTDO

N-(((9H-fluoren-9-yl)methoxy)carbonyl)-S-((3-nitropyridin-2-yl)thio)-L-cysteine

Refernces

• 1、 Atherton, Eric,Pinori, Masimo,Sheppard, Robert C.. "Peptide Synthesis. Part 6. Protection of the Sulphydryl Group of Cysteine in Solid-phase Synthesis using Nα-Fluorenylmethoxycarbonylamino Acids. Linear Oxytocin Derivatives". . p. 2057 - 2064. Retrieved 2007/10/02.