Fmoc-D-norvaline

Base Information

• Chemical Name: Fmoc-D-norvaline
• CAS No.: 144701-24-6
• Molecular Formula: C20H21NO4
• Molecular Weight: 339.391
• Hs Code.: 29225090
• DSSTox Substance ID: DTXSID80373244
• Wikidata: Q72478751
• Mol file: 144701-24-6.mol

Synonyms:Fmoc-D-Nva-OH;Fmoc-D-norvaline;144701-24-6;(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)pentanoic acid;(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)pentanoic acid;SCHEMBL119530;D-Norvaline, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-;DTXSID80373244;(2R)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)pentanoic acid;MFCD00155640;AKOS016843505;AM82598;DS-3404;CS-0101031;EN300-624040;J-300351;Z1946055110;(R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)pentanoic acid

Chemical Property of Fmoc-D-norvaline

Chemical Property:

• Appearance/Colour: White powder
• Melting Point: 152-154 °C
• Boiling Point: 557.9 °C at 760 mmHg
• PKA: 3.91±0.20(Predicted)
• Flash Point: 291.2 °C
• PSA: 75.63000
• Density: 1.23 g/cm³
• LogP: 4.16930
• Storage Temp.: 2-8°C
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 339.14705815
• Heavy Atom Count: 25
• Complexity: 458

Purity/Quality:

98%,99%, ^*data from raw suppliers

Fmoc-D-norvaline ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Isomeric SMILES: CCC[C@H](C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Uses: Fmoc-d-nva-oh is a useful intermediate for organic synthesis.

Technology Process of Fmoc-D-norvaline

There total 6 articles about Fmoc-D-norvaline 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:

2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)pentanoic acid → Fmoc-norvaline-OH (135112-28-6) + (R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)pentanoic acid (144701-24-6)

Guidance literature:

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

DOI:10.1002/bkcs.11694

Reference yield:

{1-[(E)-2-((1S,2S,5R)-2-Isopropyl-5-methyl-cyclohexyl)-vinyl]-butyl}-carbamic acid 9H-fluoren-9-ylmethyl ester → Fmoc-norvaline-OH (135112-28-6) + (R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)pentanoic acid (144701-24-6)

Guidance literature:

{1-[(E)-2-((1S,2S,5R)-2-Isopropyl-5-methyl-cyclohexyl)-vinyl]-butyl}-carbamic acid 9H-fluoren-9-ylmethyl ester; With ozone; In dichloromethane; at -78 ℃; for 0.0833333h;

With dimethylsulfide; In dichloromethane; at -78 - 20 ℃;

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In water; tert-butyl alcohol; at 20 ℃; for 5h; Title compound not separated from byproducts;

DOI:10.1021/ol052034n

Reference yield:

(fluorenylmethoxy)carbonyl chloride (28920-43-6) → Fmoc-norvaline-OH (135112-28-6) + (R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)pentanoic acid (144701-24-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium carbonate / water; 1,4-dioxane / Cooling with ice

1.2: 5 h / 20 °C

2.1: trifluoroacetic acid / isopropyl alcohol; hexane / 25 °C / Resolution of racemate

With sodium carbonate; trifluoroacetic acid; In 1,4-dioxane; hexane; water; isopropyl alcohol;

DOI:10.1002/bkcs.11694

upstream raw materials:

D-norvaline

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

2-oxopentanoic acid

(fluorenylmethoxy)carbonyl chloride

Downstream raw materials:

C₃₀H₃₁N₃O₅

(R)-2-propylpiperazine

Refernces

• 1、 Cheng, Xinkuan,Chen, Xi,Feng, Jinhui,Wu, Qiaqing,Zhu, Dunming. "Structure-guided engineering of: Meso -diaminopimelate dehydrogenase for enantioselective reductive amination of sterically bulky 2-keto acids". . p. 4994 - 5002. Retrieved 2018/10/17.