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

Base Information

• Chemical Name: Acetic acid (S)-2-phenyl-1-[(2S,4R)-4-(toluene-4-sulfonyl)-3,4-dihydro-2H-pyran-2-yl]-ethyl ester
• CAS No.: 89927-19-5
• Molecular Formula: C₂₂H₂₄O₅S
• Molecular Weight: 400.496
• Mol file: 89927-19-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 11 articles about Acetic acid (S)-2-phenyl-1-[(2S,4R)-4-(toluene-4-sulfonyl)-3,4-dihydro-2H-pyran-2-yl]-ethyl 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: 72.0%

acetic anhydride (108-24-7) + (1S,3R,5R,7S)-7-Benzyl-3-(toluene-4-sulfonyl)-6,8-dioxa-bicyclo[3.2.1]octane (89927-14-0) → Acetic acid (S)-2-phenyl-1-[(2S,4R)-4-(toluene-4-sulfonyl)-3,4-dihydro-2H-pyran-2-yl]-ethyl ester (89927-19-5)

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)-2-phenyl-1-[(2S,4R)-4-(toluene-4-sulfonyl)-3,4-dihydro-2H-pyran-2-yl]-ethyl ester (89927-19-5)

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.)Ph₂CuLi / 2.)acetylation

With boron trifluoride diethyl etherate; lithium diphenylcuprate; potassium carbonate; 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)-2-phenyl-1-[(2S,4R)-4-(toluene-4-sulfonyl)-3,4-dihydro-2H-pyran-2-yl]-ethyl ester (89927-19-5)

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.)Ph₂CuLi / 2.)acetylation

With boron trifluoride diethyl etherate; lithium diphenylcuprate; potassium carbonate; In methanol; dichloromethane;

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

upstream raw materials:

acetic anhydride

(1S,3R,5R,7S)-7-Benzyl-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