(4R)-4-[2-(benzenesulfonyl)ethyl]-2,2,4-trimethyl-1,3-dioxolane

Base Information

• Chemical Name: (4R)-4-[2-(benzenesulfonyl)ethyl]-2,2,4-trimethyl-1,3-dioxolane
• CAS No.: 80320-89-4
• Molecular Formula: C14H20O4S
• Molecular Weight: 284.376
• DSSTox Substance ID: DTXSID10568262
• Wikidata: Q82454457
• Mol file: 80320-89-4.mol

Synonyms:80320-89-4;(4R)-4-[2-(benzenesulfonyl)ethyl]-2,2,4-trimethyl-1,3-dioxolane;DTXSID10568262

Chemical Property of (4R)-4-[2-(benzenesulfonyl)ethyl]-2,2,4-trimethyl-1,3-dioxolane

Chemical Property:

• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 284.10823029
• Heavy Atom Count: 19
• Complexity: 404

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OCC(O1)(C)CCS(=O)(=O)C2=CC=CC=C2)C
• Isomeric SMILES: C[C@]1(COC(O1)(C)C)CCS(=O)(=O)C2=CC=CC=C2

Technology Process of (4R)-4-[2-(benzenesulfonyl)ethyl]-2,2,4-trimethyl-1,3-dioxolane

There total 1 articles about (4R)-4-[2-(benzenesulfonyl)ethyl]-2,2,4-trimethyl-1,3-dioxolane 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)-(-)-citramalic acid (6236-10-8,2306-22-1) → (R)-4-(2-Benzenesulfonyl-ethyl)-2,2,4-trimethyl-[1,3]dioxolane (80320-89-4)

Guidance literature:

Multistep reaction;

DOI:10.1016/S0040-4039(01)91020-2

Reference yield: 95.0%

(R)-4-(2-Benzenesulfonyl-ethyl)-2,2,4-trimethyl-[1,3]dioxolane (80320-89-4) + 2-[(3S,9S,10R,13R,14R)-17-((S)-2-Bromo-1-methyl-ethyl)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yloxy]-tetrahydro-pyran (82268-14-2) → 2-{(3S,9S,10R,13R,14R)-17-[(R)-3-Benzenesulfonyl-1-methyl-4-((R)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-butyl]-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yloxy}-tetrahydro-pyran (93489-89-5,100019-15-6,100019-16-7)

Guidance literature:

In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at -20 ℃;

DOI:10.1016/S0040-4039(01)91020-2

Reference yield: 72.0%

22-Oxo-5α,8α-(4-phenyl-3,5-dioxo-1,2,4-triazolidine-1,2-diyl)-23,24-dinor-6-cholene-1α,3β-diyl diacetate (125315-53-9) + (R)-4-(2-Benzenesulfonyl-ethyl)-2,2,4-trimethyl-[1,3]dioxolane (80320-89-4) → C46H59N3O10S (137649-12-8) + (25R)-23-(phenylsulfonyl)-5,7-cholestadiene-1α,3β,22,25,26-pentol 1,3-diacetate 25,26-acetonide 4-phenyl-1,2,4-triazoline-3,5-dione adduct (137649-11-7,137764-39-7,137764-40-0,137764-41-1,143678-88-0)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.666667h;

DOI:10.1021/jo00027a010

upstream raw materials:

(R)-(-)-citramalic acid

Downstream raw materials:

C₄₆H₅₉N₃O₁₀S

(25R)-23-(phenylsulfonyl)-5,7-cholestadiene-1α,3β,22,25,26-pentol 1,3-diacetate 25,26-acetonide 4-phenyl-1,2,4-triazoline-3,5-dione adduct

2-{(3S,9S,10R,13R,14R)-17-[(R)-3-Benzenesulfonyl-1-methyl-4-((R)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-butyl]-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yloxy}-tetrahydro-pyran

25R,26-dihydroxy-23-oxovitamin D₃