N-t-Boc-valacyclovir

Base Information

• Chemical Name: N-t-Boc-valacyclovir
• CAS No.: 502421-44-5
• Molecular Formula: C18H28N6O6
• Molecular Weight: 424.457
• Mol file: 502421-44-5.mol

Synonyms:2-[(2-Amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methoxy]ethyl N-(tert-butoxycarbonyl)-L-valinate; L-valine, N-[(1,1-dimethylethoxy)carbonyl]-, 2-[(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]ethyl ester

Chemical Property of N-t-Boc-valacyclovir

Chemical Property:

• Vapor Pressure: 0Pa at 25℃
• Boiling Point: 603.96℃
• PKA: 11.05±0.46(Predicted)
• PSA: 163.45000
• Density: 1.397g/cm³
• LogP: 1.74050
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Acetic Acid (Slightly), DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

99.9% ^*data from raw suppliers

N-t-Boc-valacyclovir ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-t-Boc-valacyclovir

There total 3 articles about N-t-Boc-valacyclovir 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:

acycloguanosine (59277-89-3) + t-Boc-L-valine (13734-41-3) → Boc-L-valacyclovir (502421-44-5)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In pyridine; dichloromethane; at 0 - 20 ℃; for 50h;

DOI:10.1016/j.ejmech.2008.08.009

Reference yield:

acycloguanosine (59277-89-3) + (S)-2-(tert-butoxycarbonylamino)-3-methylbutanoic anhydride (33294-55-2) → Boc-L-valacyclovir (502421-44-5)

Guidance literature:

With dmap; In N,N-dimethyl-formamide; at 20 ℃; for 24h;

DOI:10.1016/S1386-1425(03)00007-6

Reference yield:

t-Boc-L-valine (13734-41-3) → Boc-L-valacyclovir (502421-44-5)

Guidance literature:

Multi-step reaction with 2 steps

1: DCC / dimethylformamide / 1 h / 0 °C

2: DMAP / dimethylformamide / 24 h / 20 °C

With dmap; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide;

DOI:10.1016/S1386-1425(03)00007-6

upstream raw materials:

acycloguanosine

(S)-2-(tert-butoxycarbonylamino)-3-methylbutanoic anhydride

t-Boc-L-valine

Downstream raw materials:

valacyclovir Hydrochloride

Valacyclovir

valacyclovir

Refernces

• 1、 Chen, Yong,Alberti, Ingo,Kalia, Yogeshvar N.. "Topical iontophoretic delivery of ionizable, biolabile aciclovir prodrugs: A rational approach to improve cutaneous bioavailability". . p. 103 - 113. Retrieved 2016/01/15.
• 2、 Nashed, Yasser E,Mitra, Ashim K. "Synthesis and characterization of novel dipeptide ester prodrugs of acyclovir.". . p. 2033 - 2039. Retrieved 2007/10/03.