FMOC-D-Valine

Base Information

• Chemical Name: FMOC-D-Valine
• CAS No.: 84624-17-9
• Molecular Formula: C20H21NO4
• Molecular Weight: 339.391
• Hs Code.: 2924 29 70
• European Community (EC) Number: 837-857-2
• Nikkaji Number: J1.101.660J
• Mol file: 84624-17-9.mol

Synonyms:FMOC-D-VAL-OH;N-alpha-(9-Fluorenylmethyloxycarbonyl)-D-valine;

Chemical Property of FMOC-D-Valine

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Melting Point: 143-144 °C(lit.)
• Boiling Point: 551.8±33.0 °C(Predicted)
• PKA: 3.90±0.10(Predicted)
• PSA: 75.63000
• Density: 1.229±0.06 g/cm3(Predicted)
• LogP: 4.02520
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), DMF (Slightly), DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: Solubility in methanol (almost transparency). Slightly soluble in water.
• XLogP3: 4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 339.14705815
• Heavy Atom Count: 25
• Complexity: 470

Purity/Quality:

99% ^*data from raw suppliers

Fmoc-D-Val-OH ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Isomeric SMILES: CC(C)[C@H](C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Uses: N-Fmoc-D-valine is an N-Fmoc-protected form of D-Valine (V094200). D-Valine (an isomer of the essential amino acid L-Valine [V094205])exhibited inhibitory effects on fibroblasts that contaminated mammalian kidney cultures, allowing for selective growth epithelial cells. D-Valine is also known for its presence in the structure of Actinomycin D, an antitumour drug. D-Valine is naturally synthesized by Streptomyces antibioticus.

Technology Process of FMOC-D-Valine

There total 7 articles about FMOC-D-Valine 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: 96.0%

D-Val-OH (640-68-6,25609-85-2,7004-03-7,921-10-8) + (fluorenylmethoxy)carbonyl chloride (28920-43-6) → N-(9-fluorenylmethoxycarbonyl)-D-valine (84624-17-9)

Guidance literature:

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

Reference yield:

Fmoc-valine (126727-02-4) → Fmoc-Val-OH (68858-20-8) + N-(9-fluorenylmethoxycarbonyl)-D-valine (84624-17-9)

Guidance literature:

With trifluoroacetic acid; In hexane; isopropyl alcohol; at 25 ℃; Reagent/catalyst; Resolution of racemate;

DOI:10.1002/bkcs.11694

Reference yield:

D-Val-OH (640-68-6,25609-85-2,7004-03-7,921-10-8) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → N-(9-fluorenylmethoxycarbonyl)-D-valine (84624-17-9)

Guidance literature:

With sodium carbonate; In aq. buffer; at 37 ℃; for 10h; pH=8.0 - 9.0;

DOI:10.1039/c8cy01426d

upstream raw materials:

D-Val-OH

(fluorenylmethoxy)carbonyl chloride

9-Fluorenylmethanol

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

Downstream raw materials:

(R)-2-[(R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-methyl-butyrylamino]-3-tritylsulfanyl-propionic acid allyl ester

C₅₂H₅₆N₄O₇S

C₅₁H₅₇NO₆SSi

C₄₉H₅₃N₅O₁₀

Refernces

• 1、 Islam, Md. Fokhrul,Adhikari, Suraj,Paik, Man-Jeong,Lee, Wonjae. "Determination of Chemical and Enantiomeric Purity of α-Amino Acids and their Methyl Esters as N-Fluorenylmethoxycarbonyl Derivatives Using Amylose-derived Chiral Stationary Phases". . p. 332 - 338. Retrieved 2019/04/13.
• 2、 -. "Chiral oxazoline NNP type ligands as well as synthesis method and application thereof". Paragraph 0172; 0173; 0174. . Retrieved 2017/08/28.