O-methyl S-phenyl ((R,S)-1-{[(benzyloxy)carbonyl]amino}pent-1-yl)phosphonothiate

Base Information

• Chemical Name: O-methyl S-phenyl ((R,S)-1-{[(benzyloxy)carbonyl]amino}pent-1-yl)phosphonothiate
• CAS No.: 1261301-09-0
• Molecular Formula: C₂₀H₂₆NO₄PS
• Molecular Weight: 407.471
• Mol file: 1261301-09-0.mol

Synonyms:O-methyl S-phenyl ((R,S)-1-{[(benzyloxy)carbonyl]amino}pent-1-yl)phosphonothiate

Chemical Property of O-methyl S-phenyl ((R,S)-1-{[(benzyloxy)carbonyl]amino}pent-1-yl)phosphonothiate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of O-methyl S-phenyl ((R,S)-1-{[(benzyloxy)carbonyl]amino}pent-1-yl)phosphonothiate

There total 8 articles about O-methyl S-phenyl ((R,S)-1-{[(benzyloxy)carbonyl]amino}pent-1-yl)phosphonothiate 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: 80.0%

methyl ((R,S)-1-{[(benzyloxy)carbonyl]amino}pent-1-yl)phosphinate (1046116-51-1) + thiophenol (108-98-5) → O-methyl S-phenyl ((R,S)-1-{[(benzyloxy)carbonyl]amino}pent-1-yl)phosphonothiate (1261301-09-0)

Guidance literature:

With triethylamine; In tetrachloromethane; at 20 ℃;

DOI:10.1007/s00726-010-0561-z

Reference yield:

C14H21ClNO4P + thiophenol (108-98-5) → O-methyl S-phenyl ((R,S)-1-{[(benzyloxy)carbonyl]amino}pent-1-yl)phosphonothiate (1261301-09-0)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; optical yield given as %de; Cooling with ice;

DOI:10.1007/s00726-010-0561-z

Reference yield:

pentanal (110-62-3) → O-methyl S-phenyl ((R,S)-1-{[(benzyloxy)carbonyl]amino}pent-1-yl)phosphonothiate (1261301-09-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 1,4-dioxane / Reflux

2.1: hydrogen bromide / 6 h / Reflux

2.2: pH 6

3.1: sodium carbonate / 1,4-dioxane; water / 0 - 20 °C

4.1: diisopropyl-carbodiimide / tetrahydrofuran / 0 - 20 °C

5.1: sodium periodate / 1,4-dioxane; water / 12 h / 20 °C

6.1: thionyl chloride / dichloromethane / 2 h / 20 °C

7.1: triethylamine / dichloromethane / 20 °C / Cooling with ice

With sodium periodate; thionyl chloride; hydrogen bromide; sodium carbonate; triethylamine; diisopropyl-carbodiimide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water;

DOI:10.1007/s00726-010-0561-z

upstream raw materials:

methyl ((R,S)-1-{[(benzyloxy)carbonyl]amino}pent-1-yl)phosphinate

thiophenol

methyl hydrogen [(R,S)-1-(benzyloxycarbonylamino)pent-1-yl]phosphonate

pentanal

Downstream raw materials:

[((R,S)-1-{[(benzyloxy)carbonyl]amino}pent-1-yl)(hydroxy)phosphoryl]acetic acid

[((R,S)-1-{[(benzyloxy)carbonyl]amino}pent-1-yl)(hydroxy)phosphoryl]acetamide

[((R,S)-1-{[(benzyloxy)carbonyl]amino}pent-1-yl)(methoxy)phosphoryl]acetamide