Acetic acid (S)-1-[(2S,4R)-4-(toluene-4-sulfonyl)-3,4-dihydro-2H-pyran-2-yl]-pentyl ester

Base Information

• Chemical Name: Acetic acid (S)-1-[(2S,4R)-4-(toluene-4-sulfonyl)-3,4-dihydro-2H-pyran-2-yl]-pentyl ester
• CAS No.: 89927-18-4
• Molecular Formula: C₁₉H₂₆O₅S
• Molecular Weight: 366.478
• Mol file: 89927-18-4.mol

Synonyms:Acetic acid (S)-1-[(2S,4R)-4-(toluene-4-sulfonyl)-3,4-dihydro-2H-pyran-2-yl]-pentyl ester

Chemical Property of Acetic acid (S)-1-[(2S,4R)-4-(toluene-4-sulfonyl)-3,4-dihydro-2H-pyran-2-yl]-pentyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (S)-1-[(2S,4R)-4-(toluene-4-sulfonyl)-3,4-dihydro-2H-pyran-2-yl]-pentyl ester

There total 11 articles about Acetic acid (S)-1-[(2S,4R)-4-(toluene-4-sulfonyl)-3,4-dihydro-2H-pyran-2-yl]-pentyl ester 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: 75.0%

acetic anhydride (108-24-7) + (1S,3R,5R,7S)-7-Butyl-3-(toluene-4-sulfonyl)-6,8-dioxa-bicyclo[3.2.1]octane (89927-13-9) → Acetic acid (S)-1-[(2S,4R)-4-(toluene-4-sulfonyl)-3,4-dihydro-2H-pyran-2-yl]-pentyl ester (89927-18-4)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 1.5h;

DOI:10.1016/S0040-4039(01)91157-8

Reference yield:

{(4S,5S)-5-Hydroxymethyl-2-[2-(toluene-4-sulfonyl)-ethyl]-[1,3]dioxolan-4-yl}-methanol (88948-50-9) → Acetic acid (S)-1-[(2S,4R)-4-(toluene-4-sulfonyl)-3,4-dihydro-2H-pyran-2-yl]-pentyl ester (89927-18-4)

Guidance literature:

Multi-step reaction with 5 steps

1: sulfonation

2: intramolecular alkylation

3: 89 percent / BF₃*Et₂O / CH₂Cl₂ / 1.5 h / 0 °C

4: 95 percent / K₂CO₃ / methanol / 0.5 h / 0 °C

5: 1.)(n-Pr)2CuLi / 2.)acetylation

With boron trifluoride diethyl etherate; potassium carbonate; di-n-propylcopperlithium; In methanol; dichloromethane;

DOI:10.1016/S0040-4039(01)91157-8

Reference yield:

(4R,5R)-2-[2-(Toluene-4-sulfonyl)-ethyl]-[1,3]dioxolane-4,5-dicarboxylic acid diethyl ester (88948-49-6) → Acetic acid (S)-1-[(2S,4R)-4-(toluene-4-sulfonyl)-3,4-dihydro-2H-pyran-2-yl]-pentyl ester (89927-18-4)

Guidance literature:

Multi-step reaction with 6 steps

1: reduction

2: sulfonation

3: intramolecular alkylation

4: 89 percent / BF₃*Et₂O / CH₂Cl₂ / 1.5 h / 0 °C

5: 95 percent / K₂CO₃ / methanol / 0.5 h / 0 °C

6: 1.)(n-Pr)2CuLi / 2.)acetylation

With boron trifluoride diethyl etherate; potassium carbonate; di-n-propylcopperlithium; In methanol; dichloromethane;

DOI:10.1016/S0040-4039(01)91157-8

upstream raw materials:

acetic anhydride

(1S,3R,5R,7S)-7-Butyl-3-(toluene-4-sulfonyl)-6,8-dioxa-bicyclo[3.2.1]octane

(2S,4R)-2-(S)-Oxiranyl-4-(toluene-4-sulfonyl)-3,4-dihydro-2H-pyran

β-p-tosylpropanal diethyl acetal

Downstream raw materials:

Acetic acid (S)-1-[(S)-6-hydroxy-4-(toluene-4-sulfonyl)-3,6-dihydro-2H-pyran-2-yl]-pentyl ester

Acetic acid (S)-1-[(S)-6-oxo-4-(toluene-4-sulfonyl)-3,6-dihydro-2H-pyran-2-yl]-pentyl ester

(S)-6-((S)-1-hydroxypentyl)-4-methoxy-5,6-dihydro-2H-pyran-2-one