L-Alanine,N-(2',3'-didehydro-3'-deoxy-P-phenyl-5'-thymidylyl)-, methyl ester

Base Information

• Chemical Name: L-Alanine,N-(2',3'-didehydro-3'-deoxy-P-phenyl-5'-thymidylyl)-, methyl ester
• CAS No.: 173070-83-2
• Molecular Formula: C20H24 N3 O8 P
• Molecular Weight: 465.4
• Mol file: 173070-83-2.mol

Synonyms:So 324

Chemical Property of L-Alanine,N-(2',3'-didehydro-3'-deoxy-P-phenyl-5'-thymidylyl)-, methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of L-Alanine,N-(2',3'-didehydro-3'-deoxy-P-phenyl-5'-thymidylyl)-, methyl ester

There total 4 articles about L-Alanine,N-(2',3'-didehydro-3'-deoxy-P-phenyl-5'-thymidylyl)-, methyl ester 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: 88.0%

stavudin (3056-17-5) + phenyl methoxyalaninyl phosphorochloridate (142629-80-9) → So324 (173070-83-2)

Guidance literature:

With 1-methyl-1H-imidazole; In tetrahydrofuran; for 4h; Ambient temperature;

DOI:10.1021/jm950605j

Reference yield:

L-Alanine methyl ester (10065-72-2) + C16H17N2O6P (834918-60-4) → So324 (173070-83-2)

Guidance literature:

With N-chloro-succinimide; triethylamine; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1055/s-2005-917085

Reference yield:

phenyl phosphorodichloridite (3426-89-9) → So324 (173070-83-2)

Guidance literature:

Multi-step reaction with 2 steps

1: t-BuOH; Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

2: N-chlorosuccinimide; Et₃N / CH₂Cl₂ / 2 h / 20 °C

With N-chloro-succinimide; triethylamine; tert-butyl alcohol; In dichloromethane; 1: Arbuzov reaction;

DOI:10.1055/s-2005-917085

upstream raw materials:

stavudin

phenyl methoxyalaninyl phosphorochloridate

L-Alanine methyl ester

C₁₆H₁₇N₂O₆P

Downstream raw materials:

stavudin

phenol

alaninyl-d4T-monophosphate

Refernces

• 1、 McGuigan, Christopher,Cahard, Dominique,Sheeka, Hendrika M.,De Clercq, Erik,Balzarini, Jan. "Phosphoramidate derivatives of d4T with improved anti-HIV efficacy retain fullactivity in thymidine kinase-deficient cells". . p. 1183 - 1186. Retrieved 1996.
• 2、 Venkatachalam,Tai, Hung-Liang,Vig, Rakesh,Chen, Chun-Lin,Jan, Shyi-Tai,Uckun, Fatih M.. "Enhancing effects of a mono-bromo substitution at the para position of the phenyl moiety on the metabolism and anti-HIV activity of d4T-phenyl methoxyalaninyl phosphate derivatives". . p. 3121 - 3126. Retrieved 2007/10/03.