BENZOIC ACID (2S,4S,4'R)-2',2'-DIMETHYL-[4,4']BI[[1,3]DIOXOLANYL]-2-YLMETHYL ESTER

Base Information

• Chemical Name: BENZOIC ACID (2S,4S,4'R)-2',2'-DIMETHYL-[4,4']BI[[1,3]DIOXOLANYL]-2-YLMETHYL ESTER
• CAS No.: 145354-79-6
• Molecular Formula: C₁₆H₂₀O₆
• Molecular Weight: 308.331
• Mol file: 145354-79-6.mol

Synonyms:[4,4'-Bi-1,3-dioxolane]-2-methanol,2',2'-dimethyl-, benzoate, (2S,4S,4'R)- (9CI); [4,4'-Bi-1,3-dioxolane]-2-methanol,2',2'-dimethyl-, benzoate, [2S-[2a,4a(S*)]]-

Chemical Property of BENZOIC ACID (2S,4S,4'R)-2',2'-DIMETHYL-[4,4']BI[[1,3]DIOXOLANYL]-2-YLMETHYL ESTER

Chemical Property:

• Boiling Point: 401.5±40.0 °C(Predicted)
• PSA: 63.22000
• Density: 1.199±0.06 g/cm3(Predicted)
• LogP: 1.73640

Purity/Quality:

(2S,4S,4'R)-2',2'-DIMETHYL-[4,4']BI[[1,3]DIOXOLANYL]-2-YL BENZOIC ACID METHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (2S,4S,4''R)-2'',2''-Dimethyl-[4,4''-bi-1,3-dioxolane]-2-methanol 2-Benzoate is an intermediate used in the synthesis of Troxacitabine (T805580), which is a nucleoside analogue with potential anticancer activity. Troxacitabine have been studied in patients with refractory lymphoproliferative diseases.

Technology Process of BENZOIC ACID (2S,4S,4'R)-2',2'-DIMETHYL-[4,4']BI[[1,3]DIOXOLANYL]-2-YLMETHYL ESTER

There total 2 articles about BENZOIC ACID (2S,4S,4'R)-2',2'-DIMETHYL-[4,4']BI[[1,3]DIOXOLANYL]-2-YLMETHYL 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:

(R)-1-((2S,4S)-2-Hydroxymethyl-[1,3]dioxolan-4-yl)-ethane-1,2-diol → Benzoic acid (2S,4S,4'R)-2',2'-dimethyl-[4,4']bi[[1,3]dioxolanyl]-2-ylmethyl ester (145354-79-6)

Guidance literature:

Multi-step reaction with 2 steps

1: p-TsOH / Ambient temperature

2: pyridine / CH₂Cl₂ / Ambient temperature

With pyridine; toluene-4-sulfonic acid; In dichloromethane;

DOI:10.1016/S0040-4039(00)60890-0

Reference yield:

benzoyl chloride (98-88-4) + ((2S,4S,4'R)-2',2'-Dimethyl-[4,4']bi[[1,3]dioxolanyl]-2-yl)-methanol (145354-78-5) → Benzoic acid (2S,4S,4'R)-2',2'-dimethyl-[4,4']bi[[1,3]dioxolanyl]-2-ylmethyl ester (145354-79-6)

Guidance literature:

With pyridine; In dichloromethane; Ambient temperature;

DOI:10.1016/S0040-4039(00)60890-0

Reference yield:

Benzoic acid (2S,4S,4'R)-2',2'-dimethyl-[4,4']bi[[1,3]dioxolanyl]-2-ylmethyl ester (145354-79-6) → (2S,4S)-2-Benzoyloxymethyl-[1,3]dioxolane-4-carboxylic acid (145354-81-0)

Guidance literature:

Multi-step reaction with 2 steps

1: p-TsOH / methanol / Ambient temperature

2: NaIO₄ / RuO₂ / acetonitrile; CCl₄; H₂O / Ambient temperature

With sodium periodate; toluene-4-sulfonic acid; ruthenium(IV) oxide; In methanol; tetrachloromethane; water; acetonitrile;

DOI:10.1016/S0040-4039(00)60890-0

upstream raw materials:

benzoyl chloride

((2S,4S,4'R)-2',2'-Dimethyl-[4,4']bi[[1,3]dioxolanyl]-2-yl)-methanol

Downstream raw materials:

(2S,4S)-2-Benzoyloxymethyl-[1,3]dioxolane-4-carboxylic acid

(2S,4RS)-4-acetoxy-2-<(benzoyloxy)methyl>dioxolane

Benzoic acid (2S,4S)-4-(4-hydroxy-5-methyl-2-oxo-2H-pyrimidin-1-yl)-[1,3]dioxolan-2-ylmethyl ester

Benzoic acid (2S,4R)-4-(4-hydroxy-5-methyl-2-oxo-2H-pyrimidin-1-yl)-[1,3]dioxolan-2-ylmethyl ester

Refernces