(2R,3S,4S)-4-(p-methoxybenzyl)thio-2,3-(isopropylidenedioxy)-1-cyclopentanone

Base Information

• Chemical Name: (2R,3S,4S)-4-(p-methoxybenzyl)thio-2,3-(isopropylidenedioxy)-1-cyclopentanone
• CAS No.: 406217-08-1
• Molecular Formula: C₁₆H₂₀O₄S
• Molecular Weight: 308.398
• Mol file: 406217-08-1.mol

Synonyms:(2R,3S,4S)-4-(p-methoxybenzyl)thio-2,3-(isopropylidenedioxy)-1-cyclopentanone

Chemical Property of (2R,3S,4S)-4-(p-methoxybenzyl)thio-2,3-(isopropylidenedioxy)-1-cyclopentanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4S)-4-(p-methoxybenzyl)thio-2,3-(isopropylidenedioxy)-1-cyclopentanone

There total 1 articles about (2R,3S,4S)-4-(p-methoxybenzyl)thio-2,3-(isopropylidenedioxy)-1-cyclopentanone 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: 99.0%

(3aR,6aR)-2,2-Dimethyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one (115509-13-2) + p-methoxybenzylmercaptan (6258-60-2) → (2R,3S,4S)-4-(p-methoxybenzyl)thio-2,3-(isopropylidenedioxy)-1-cyclopentanone (406217-08-1)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1016/S0968-0896(01)00271-1

Reference yield: 60.0%

(2R,3S,4S)-4-(p-methoxybenzyl)thio-2,3-(isopropylidenedioxy)-1-cyclopentanone (406217-08-1) → (1S,2S,3S,4S)-4-(p-methoxybenzyl)thio-2,3-(isopropylidenedioxy)cyclopentan-1-ol (406217-09-2)

Guidance literature:

With borane-THF; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1016/S0968-0896(01)00271-1

Reference yield:

(2R,3S,4S)-4-(p-methoxybenzyl)thio-2,3-(isopropylidenedioxy)-1-cyclopentanone (406217-08-1) → 9-[(1'R,2'S,3'S,4'S)-4'-(p-methoxybenzyl)thio-2',3'-(isopropylidenedioxy)cyclopentan-1'-yl]-6-chloropurine

Guidance literature:

Multi-step reaction with 2 steps

1.1: 60 percent / BH₃*THF / tetrahydrofuran / 3 h / 20 °C

2.1: diisopropyl azodicarboxylate; PPh₃ / tetrahydrofuran / 0.5 h

2.2: tetrahydrofuran / 20 h

With borane-THF; di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; 2.1: Mitsunobu reaction / 2.2: Mitsunobu reaction;

DOI:10.1016/S0968-0896(01)00271-1

upstream raw materials:

(3aR,6aR)-2,2-Dimethyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one

p-methoxybenzylmercaptan

Downstream raw materials:

(1S,2S,3S,4S)-4-(p-methoxybenzyl)thio-2,3-(isopropylidenedioxy)cyclopentan-1-ol

9-[(1'R,2'S,3'S,4'S)-4'-(p-methoxybenzyl)thio-2',3'-(isopropylidenedioxy)cyclopentan-1'-yl]adenine