(4S,5S)-5-(hydroxydiphenylmethyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylic acid

Base Information

• Chemical Name: (4S,5S)-5-(hydroxydiphenylmethyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylic acid
• CAS No.: 173097-64-8
• Molecular Formula: C₁₉H₂₀O₅
• Molecular Weight: 328.365
• Mol file: 173097-64-8.mol

Synonyms:(4S,5S)-5-(hydroxydiphenylmethyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylic acid

Chemical Property of (4S,5S)-5-(hydroxydiphenylmethyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S)-5-(hydroxydiphenylmethyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylic acid

There total 1 articles about (4S,5S)-5-(hydroxydiphenylmethyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylic acid 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:

bromobenzene (108-86-1,52753-63-6) + methyl (4S,5S)-2,2-dimethyl-1,3-dioxolane-4-carboxylic acid-5-carboxylate (67844-12-6) → (4S,5S)-5-(hydroxydiphenylmethyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylic acid (173097-64-8)

Guidance literature:

With magnesium; Yield given. Multistep reaction; 2.) THF, 1 h, 20-30 deg C;

DOI:10.1002/hlca.19950780703

Reference yield: 93.0%

(4S,5S)-5-(hydroxydiphenylmethyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylic acid (173097-64-8) + methyl iodide (74-88-4) → methyl (4S,5S)-5-(hydroxydiphenylmethyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate (173097-65-9)

Guidance literature:

With sodium carbonate; In N,N-dimethyl-formamide; for 48h; Ambient temperature;

DOI:10.1002/hlca.19950780703

Reference yield:

(4S,5S)-5-(hydroxydiphenylmethyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylic acid (173097-64-8) → (4S,5S)-4-<(diphenylphosphanyl)methyl>-5-(methoxydiphenylmethyl)-2,2-dimethyl-1,3-dioxolane

Guidance literature:

Multi-step reaction with 5 steps

1: 93 percent / Na₂CO₃ / dimethylformamide / 48 h / Ambient temperature

2: 93 percent / NaBH₄ / methanol

3: 79 percent / PPh₃, CCl₄ / 50 °C

4: 97 percent / NaH / tetrahydrofuran; paraffin

5: 1.) BuLi / 1.) THF/hexane, RT, 30 min, 2.) THF/hexane

With tetrachloromethane; sodium tetrahydroborate; n-butyllithium; sodium hydride; sodium carbonate; triphenylphosphine; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; paraffin;

DOI:10.1002/hlca.19950780703

upstream raw materials:

bromobenzene

methyl (4S,5S)-2,2-dimethyl-1,3-dioxolane-4-carboxylic acid-5-carboxylate

Downstream raw materials:

methyl (4S,5S)-5-(hydroxydiphenylmethyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate

((4S,5S)-5-Chloromethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-diphenyl-methanol

(4S,5R)-5-(hydroxydiphenylmethyl)-2,2-dimethyl-1,3-dioxolane-4-methanol

(4S,5S)-4-(chloromethyl)-5-(methoxydiphenylmethyl)-2,2-dimethyl-1,3-dioxolane