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

Base Information

• Chemical Name: Acetic acid (S)-1-[(2S,4R)-4-(toluene-4-sulfonyl)-3,4-dihydro-2H-pyran-2-yl]-undecyl ester
• CAS No.: 88948-54-3
• Molecular Formula: C₂₅H₃₈O₅S
• Molecular Weight: 450.64
• Mol file: 88948-54-3.mol

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

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

There total 11 articles about Acetic acid (S)-1-[(2S,4R)-4-(toluene-4-sulfonyl)-3,4-dihydro-2H-pyran-2-yl]-undecyl 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-Decyl-3-(toluene-4-sulfonyl)-6,8-dioxa-bicyclo[3.2.1]octane (88948-53-2) → Acetic acid (S)-1-[(2S,4R)-4-(toluene-4-sulfonyl)-3,4-dihydro-2H-pyran-2-yl]-undecyl ester (88948-54-3)

Guidance literature:

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

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]-undecyl ester (88948-54-3)

Guidance literature:

Multi-step reaction with 2 steps

2: 72 percent / BF₃-Et₂O / CH₂Cl₂ / 1.5 h / 0 °C

With boron trifluoride diethyl etherate; In dichloromethane;

DOI:10.1246/cl.1983.1835

Reference yield:

Toluene-4-sulfonic acid (1S,3R,5S,7S)-3-(toluene-4-sulfonyl)-6,8-dioxa-bicyclo[3.2.1]oct-7-ylmethyl ester (88948-52-1) → Acetic acid (S)-1-[(2S,4R)-4-(toluene-4-sulfonyl)-3,4-dihydro-2H-pyran-2-yl]-undecyl ester (88948-54-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / Me₂S / diethyl ether / 6 h / -20 - -15 °C

2: 72 percent / BF₃-Et₂O / CH₂Cl₂ / 1.5 h / 0 °C

With dimethylsulfide; boron trifluoride diethyl etherate; In diethyl ether; dichloromethane;

DOI:10.1246/cl.1983.1835

upstream raw materials:

acetic anhydride

(1S,3R,5R,7S)-7-Decyl-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:

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

(R)-1-[(S)-6-benzyloxy-tetrahydro-2H-pyran-2-yl]undecan-1-ol

(R)-1-acetoxy-[(S)-6-benzyloxy-tetrahydro-2H-pyran-2-yl]undecane

Benzoic acid (R)-1-[(2S,4R)-6-benzyloxy-4-(toluene-4-sulfonyl)-tetrahydro-pyran-2-yl]-undecyl ester