Boc-3-(1-naphthyl)-D-alanine

Base Information

• Chemical Name: Boc-3-(1-naphthyl)-D-alanine
• CAS No.: 76932-48-4
• Molecular Formula: C₁₈H₂₁NO₄
• Molecular Weight: 315.369
• Hs Code.: 29242990
• DSSTox Substance ID: DTXSID50370341
• Nikkaji Number: J3.110.224C
• Wikidata: Q72450137
• Mol file: 76932-48-4.mol

Synonyms:76932-48-4;Boc-D-1-Nal-OH;Boc-3-(1-naphthyl)-D-alanine;BOC-D-1-NAPHTHYLALANINE;N-(tert-Butoxycarbonyl)-3-(1-naphthyl)-D-alanine;(R)-2-((tert-Butoxycarbonyl)amino)-3-(naphthalen-1-yl)propanoic acid;(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-naphthalen-1-ylpropanoic acid;N-Boc-3-(1-naphthyl)-D-alanine;MFCD00079668;Boc-D-3-(1-Naphthyl )-alanine;SCHEMBL4600435;Boc-D-1-Nal-OH, 97%;BOC-D-ALA(1-NAPH)-OH;DTXSID50370341;KHHIGWRTNILXLL-OAHLLOKOSA-N;BOC-3-(1-NAPHTHYL)-D-ALA;(R)-2-TERT-BUTOXYCARBONYLAMINO-3-NAPHTHALEN-1-YL-PROPIONIC ACID;AKOS016843559;AC-9932;AM83697;CS-W012038;HY-W011322;DS-15332;Boc-D-1-Naphthylalanine (Boc-D-1Nal-OH);B3615;Boc-D-1-Nal-OH, >=98.0% (TLC);3-(NAPHTHALEN-1-YL)-N-BOC-D-ALANINE;EN300-3403506;(R)-alpha-(Boc-amino)-1-naphthalenepropionic Acid;N-(tert-Butoxycarbonyl)-3-naphthalen-1-yl-D-alanine;(R)-alpha-tert-Butoxycarbonylamino-1-naphthalenepropionic Acid;(2R)-2-{[(tert-butoxy)carbonyl]amino}-3-(naphthalen-1-yl)propanoic acid;(R)-2-(TERT-BUTOXYCARBONYLAMINO)-3-(NAPHTHALEN-1-YL)PROPANOIC ACID

Chemical Property of Boc-3-(1-naphthyl)-D-alanine

Chemical Property:

• Appearance/Colour: off-white to yellowish crystalline powder
• Vapor Pressure: 2.58E-11mmHg at 25°C
• Melting Point: 145-148 °C(lit.)
• Refractive Index: 1.5740 (estimate)
• Boiling Point: 512.2 °C at 760 mmHg
• PKA: 3.88±0.30(Predicted)
• Flash Point: 263.6 °C
• PSA: 66.84000
• Density: 1.2 g/cm³
• LogP: 4.05440
• Storage Temp.: Store at 0-5°C
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 315.14705815
• Heavy Atom Count: 23
• Complexity: 429

Purity/Quality:

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

Boc-D-1-Nal-OH ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CC=CC2=CC=CC=C21)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@H](CC1=CC=CC2=CC=CC=C21)C(=O)O
• Uses: Boc-D-1-Nal-OH is an antiviral.

Technology Process of Boc-3-(1-naphthyl)-D-alanine

There total 22 articles about Boc-3-(1-naphthyl)-D-alanine 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: 100.0%

di-tert-butyl dicarbonate (24424-99-5) + L-1-naphthylalanine (55516-54-6,68798-79-8,7758-42-1) → (S)-2-tert-butoxycarbonylamino-3-naphthalen-1-yl-propionic acid (55447-00-2,76932-48-4,103190-32-5,104882-22-6)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; pH 10;

DOI:10.1016/0223-5234(91)90056-S

Reference yield: 95.0%

tert-butyl chloroformate (24608-52-4) + L-3-(naphthalen-1-yl)alanine hydrochloride → (S)-2-tert-butoxycarbonylamino-3-naphthalen-1-yl-propionic acid (55447-00-2,76932-48-4,103190-32-5,104882-22-6)

Guidance literature:

With sodium hydroxide; In water; at 0 - 20 ℃; for 1h;

DOI:10.3987/COM-13-12694

Reference yield: 92.4%

(RS)-S-ethyl 2-(tert-butoxycarbonylamino)-3-(naphthalen-1-yl)propanethioate (1393112-49-6) → C20H25NO3S + (S)-2-tert-butoxycarbonylamino-3-naphthalen-1-yl-propionic acid (55447-00-2,76932-48-4,103190-32-5,104882-22-6)

Guidance literature:

With alcalase CLEA; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tert-butyl alcohol; at 37 ℃; for 144h; optical yield given as %ee; enantioselective reaction; Resolution of racemate; Enzymatic reaction;

DOI:10.1016/j.tetasy.2012.06.020

upstream raw materials:

di-tert-butyl dicarbonate

L-1-naphthylalanine

(2S)-2-<(tert-butoxycarbonyl)amino>-3-(1-naphthyl)-1-propanol

(2R,3R)-3-(tert-butoxycarbonylamino)-3-(1-naphthyl)-1,2-propanediol

Downstream raw materials:

Boc-Glu(OMe)-napAla-Glu(OMe)2-OBzl

napAla-Glu(OBzl)4-OBzl

(S)-3-[(S)-2-((S)-2-tert-Butoxycarbonylamino-3-naphthalen-1-yl-propionylamino)-hexanoylamino]-N-((S)-1-carbamoyl-2-phenyl-ethyl)-succinamic acid

(S)-3-{(S)-2-[(S)-2-(2-{(S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-hexanoylamino}-acetylamino)-3-naphthalen-1-yl-propionylamino]-hexanoylamino}-N-((S)-1-carbamoyl-2-phenyl-ethyl)-succinamic acid

Refernces

• 1、 D'Arrigo, Paola,Cerioli, Lorenzo,Fiorati, Andrea,Servi, Stefano,Viani, Fiorenza,Tessaro, Davide. "Naphthyl-l-α-amino acids via chemo-enzymatic dynamic kinetic resolution". experimental part. p. 938 - 944. Retrieved 2012/10/08.
• 2、 Medina,Moyano,Pericas,Riera. "Synthesis of N-Boc-β-aryl alanines and of N-Boc-β-methyl-β-aryl alanines by regioselective ring-opening of enantiomerically pure N-Boc- aziridines". . p. 8574 - 8578. Retrieved 2007/10/03.