(P_S*,2S^*)-Ethyl 2-benzylphospholanate

Base Information

• Chemical Name: (P_S*,2S^*)-Ethyl 2-benzylphospholanate
• CAS No.: 133471-45-1
• Molecular Formula: C₁₃H₁₉O₂P
• Molecular Weight: 238.266
• Mol file: 133471-45-1.mol

Synonyms:

Chemical Property of (P_S*,2S^*)-Ethyl 2-benzylphospholanate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (P_S*,2S^*)-Ethyl 2-benzylphospholanate

There total 2 articles about (P_S*,2S^*)-Ethyl 2-benzylphospholanate 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:

benzyl bromide (100-39-0) + Ethyl phospholanate (10545-61-6) → (PS*,2R*)-Ethyl 2-benzylphospholanate (133471-45-1,133471-47-3) + (PS*,2S*)-Ethyl 2-benzylphospholanate (133471-45-1,133471-47-3)

Guidance literature:

With Li-tetramethylpiperidide; In tetrahydrofuran; at -78 ℃; Product distribution; same alkylation reaction of other phospholanes; addition of HMPA as cosolvent; stereoselectivity;

DOI:10.1021/jo00009a039

Reference yield:

benzyl bromide (100-39-0) + Ethyl phospholanate (10545-61-6) → (PS*,2R*)-Ethyl 2-benzylphospholanate (133471-45-1,133471-47-3) + (PS*,2S*)-Ethyl 2-benzylphospholanate (133471-45-1,133471-47-3)

Guidance literature:

With Li-tetramethylpiperidide; In tetrahydrofuran; at -78 ℃; Product distribution; same alkylation reaction of other phospholanes; addition of HMPA as cosolvent; stereoselectivity;

DOI:10.1021/jo00009a039

Reference yield:

(PS*,2R*)-Ethyl 2-benzylphospholanate (133471-45-1,133471-47-3) → (2S*,5S*)-2,5-dibenzyl phospholanic acid (133471-51-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Li-tetramethylpiperidide / THF; 1.) -78 deg C, 1 h; 2.) -78 deg C, 2 h; addition of HMPA as cosolvent

2: 85 percent / trimethylsilyl bromide / CH₂Cl₂ / 20 h / Ambient temperature

With trimethylsilyl bromide; Li-tetramethylpiperidide; In dichloromethane;

DOI:10.1021/jo00009a039

upstream raw materials:

benzyl bromide

Ethyl phospholanate

Downstream raw materials:

(2S^*,5S^*)-2,5-dibenzyl phospholanic acid

(2S^*,5S^*)-1,2,5-Tribenzyl-1-oxophospholane