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

Base Information

• Chemical Name: Benzoic acid (R)-1-[(2S,4R)-4-(toluene-4-sulfonyl)-3,4-dihydro-2H-pyran-2-yl]-undecyl ester
• CAS No.: 88948-56-5
• Molecular Formula: C₃₀H₄₀O₅S
• Molecular Weight: 512.711
• Mol file: 88948-56-5.mol

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

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

There total 5 articles about Benzoic acid (R)-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: 81.0%

Acetic acid (S)-1-[(2S,4R)-4-(toluene-4-sulfonyl)-3,4-dihydro-2H-pyran-2-yl]-undecyl ester (88948-54-3) + benzoic acid (65-85-0,8013-63-6) → Benzoic acid (R)-1-[(2S,4R)-4-(toluene-4-sulfonyl)-3,4-dihydro-2H-pyran-2-yl]-undecyl ester (88948-56-5)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20 ℃; for 20h;

DOI:10.1246/cl.1983.1835

Reference yield:

β-p-tosylpropanal diethyl acetal (88948-48-5) → Benzoic acid (R)-1-[(2S,4R)-4-(toluene-4-sulfonyl)-3,4-dihydro-2H-pyran-2-yl]-undecyl ester (88948-56-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 79 percent / p-TsOH / toluene / 4 h / 120 °C

3: 72 percent / BF₃-Et₂O / CH₂Cl₂ / 1.5 h / 0 °C

4: 81 percent / EtO₂CNNCO₂Et, PH₃P / tetrahydrofuran / 20 h / 20 °C

With boron trifluoride diethyl etherate; toluene-4-sulfonic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; toluene;

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) → Benzoic acid (R)-1-[(2S,4R)-4-(toluene-4-sulfonyl)-3,4-dihydro-2H-pyran-2-yl]-undecyl ester (88948-56-5)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: 81 percent / EtO₂CNNCO₂Et, PH₃P / tetrahydrofuran / 20 h / 20 °C

With dimethylsulfide; boron trifluoride diethyl etherate; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1246/cl.1983.1835

upstream raw materials:

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

benzoic acid

β-p-tosylpropanal diethyl acetal

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

Downstream raw materials:

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

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

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