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

Base Information

• Chemical Name: (1S,2S,3S,4S)-4-(p-methoxybenzyl)thio-2,3-(isopropylidenedioxy)cyclopentan-1-ol
• CAS No.: 406217-09-2
• Molecular Formula: C₁₆H₂₂O₄S
• Molecular Weight: 310.414
• Mol file: 406217-09-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about (1S,2S,3S,4S)-4-(p-methoxybenzyl)thio-2,3-(isopropylidenedioxy)cyclopentan-1-ol 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: 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:

(3aR,6aR)-2,2-Dimethyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one (115509-13-2) → (1S,2S,3S,4S)-4-(p-methoxybenzyl)thio-2,3-(isopropylidenedioxy)cyclopentan-1-ol (406217-09-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / K₂CO₃ / tetrahydrofuran / 3 h / 20 °C

2: 60 percent / BH₃*THF / tetrahydrofuran / 3 h / 20 °C

With borane-THF; potassium carbonate; In tetrahydrofuran; 1: Michael addition reaction;

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

Reference yield:

p-methoxybenzylmercaptan (6258-60-2) → (1S,2S,3S,4S)-4-(p-methoxybenzyl)thio-2,3-(isopropylidenedioxy)cyclopentan-1-ol (406217-09-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / K₂CO₃ / tetrahydrofuran / 3 h / 20 °C

2: 60 percent / BH₃*THF / tetrahydrofuran / 3 h / 20 °C

With borane-THF; potassium carbonate; In tetrahydrofuran; 1: Michael addition reaction;

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

upstream raw materials:

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

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

p-methoxybenzylmercaptan

Downstream raw materials:

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