bis[(1R,2S,5R)-menthyl] ((S)-3-chloro-2-hydroxypropyl)phosphonate

Base Information

• Chemical Name: bis[(1R,2S,5R)-menthyl] ((S)-3-chloro-2-hydroxypropyl)phosphonate
• CAS No.: 900537-05-5
• Molecular Formula: C₂₃H₄₄ClO₄P
• Molecular Weight: 451.027
• Mol file: 900537-05-5.mol

Synonyms:bis[(1R,2S,5R)-menthyl] ((S)-3-chloro-2-hydroxypropyl)phosphonate

Chemical Property of bis[(1R,2S,5R)-menthyl] ((S)-3-chloro-2-hydroxypropyl)phosphonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of bis[(1R,2S,5R)-menthyl] ((S)-3-chloro-2-hydroxypropyl)phosphonate

There total 4 articles about bis[(1R,2S,5R)-menthyl] ((S)-3-chloro-2-hydroxypropyl)phosphonate 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: 94.0%

di(1R,2S,5R)-menthyl 2-keto-3-chloropropylphosphonate (900537-08-8) → bis[(1R,2S,5R)-menthyl] ((S)-3-chloro-2-hydroxypropyl)phosphonate (900537-05-5)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; at -30 ℃;

DOI:10.1016/j.tet.2007.04.101

Reference yield:

di(1R,2S,5R)-menthyl 2-keto-3-chloropropylphosphonate (900537-08-8) → bis[(1R,2S,5R)-menthyl] ((S)-3-chloro-2-hydroxypropyl)phosphonate (900537-05-5) + di(1R,2S,5R)-menthyl [(R)-2-hydroxy-3-chloropropyl]phosphonate (945652-59-5)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; at -30 ℃; for 24h;

DOI:10.1016/j.tet.2007.04.101

Reference yield:

di(1R,2S,5R)-menthyl methylphosphonate (900537-07-7) → bis[(1R,2S,5R)-menthyl] ((S)-3-chloro-2-hydroxypropyl)phosphonate (900537-05-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / -78 °C

1.2: Cu₂Br₂ / tetrahydrofuran; hexane / 1.5 h / -60 - -30 °C

1.3: 80 percent / tetrahydrofuran; hexane / -40 - -30 °C

2.1: 94 percent / sodium borohydride; (R,R)-(+)-tartaric acid / tetrahydrofuran / -30 °C

With sodium tetrahydroborate; n-butyllithium; In tetrahydrofuran; hexane;

DOI:10.1016/j.tet.2007.04.101

upstream raw materials:

di(1R,2S,5R)-menthyl 2-keto-3-chloropropylphosphonate

di(1R,2S,5R)-menthyl methylphosphonate

(-)-menthol

Downstream raw materials:

bis[(1R,2S,5R)-menthyl] (2R)-(oxiran-2-yl)-methylphosphonate

bis[(1R,2S,5R)-menthyl] [(2R)-3-(dibenzylamino)-2-hydroxypropyl]phosphonate

di(1R,2S,5R)-menthyl (2R)-2-hydroxy-3-azidopropylphosphonate