(4R,5R)-2-[2-(Toluene-4-sulfonyl)-ethyl]-[1,3]dioxolane-4,5-dicarboxylic acid diethyl ester

Base Information

• Chemical Name: (4R,5R)-2-[2-(Toluene-4-sulfonyl)-ethyl]-[1,3]dioxolane-4,5-dicarboxylic acid diethyl ester
• CAS No.: 88948-49-6
• Molecular Formula: C₁₈H₂₄O₈S
• Molecular Weight: 400.45
• Mol file: 88948-49-6.mol

Synonyms:(4R,5R)-2-[2-(Toluene-4-sulfonyl)-ethyl]-[1,3]dioxolane-4,5-dicarboxylic acid diethyl ester

Chemical Property of (4R,5R)-2-[2-(Toluene-4-sulfonyl)-ethyl]-[1,3]dioxolane-4,5-dicarboxylic acid diethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5R)-2-[2-(Toluene-4-sulfonyl)-ethyl]-[1,3]dioxolane-4,5-dicarboxylic acid diethyl ester

There total 2 articles about (4R,5R)-2-[2-(Toluene-4-sulfonyl)-ethyl]-[1,3]dioxolane-4,5-dicarboxylic acid diethyl 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: 79.0%

β-p-tosylpropanal diethyl acetal (88948-48-5) + diethyl tartrate (21066-72-8) → (4R,5R)-2-[2-(Toluene-4-sulfonyl)-ethyl]-[1,3]dioxolane-4,5-dicarboxylic acid diethyl ester (88948-49-6)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; at 120 ℃; for 4h;

DOI:10.1246/cl.1983.1835

Reference yield:

diethyl (2R,3R)-tartrate (87-91-2) + β-p-tosylpropanal diethyl acetal (88948-48-5) → (4R,5R)-2-[2-(Toluene-4-sulfonyl)-ethyl]-[1,3]dioxolane-4,5-dicarboxylic acid diethyl ester (88948-49-6)

Guidance literature:

acetalization;

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

upstream raw materials:

diethyl (2R,3R)-tartrate

β-p-tosylpropanal diethyl acetal

diethyl tartrate

Downstream raw materials:

{(4S,5S)-5-Hydroxymethyl-2-[2-(toluene-4-sulfonyl)-ethyl]-[1,3]dioxolan-4-yl}-methanol

Acetic acid (S)-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