(4R,5S)-methyl 5-phenyl-2-thioxo-1,3-dioxolane-4-carboxylate

Base Information

• Chemical Name: (4R,5S)-methyl 5-phenyl-2-thioxo-1,3-dioxolane-4-carboxylate
• CAS No.: 959123-34-3
• Molecular Formula: C₁₀H₁₀O₅S
• Molecular Weight: 242.252
• Mol file: 959123-34-3.mol

Synonyms:(4R,5S)-methyl 5-phenyl-2-thioxo-1,3-dioxolane-4-carboxylate

Chemical Property of (4R,5S)-methyl 5-phenyl-2-thioxo-1,3-dioxolane-4-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5S)-methyl 5-phenyl-2-thioxo-1,3-dioxolane-4-carboxylate

There total 2 articles about (4R,5S)-methyl 5-phenyl-2-thioxo-1,3-dioxolane-4-carboxylate 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: 98.0%

methyl (2R,3S)-2,3-dihydroxy-3-phenylpropanoate (122743-18-4) → (4R,5S)-methyl 5-phenyl-2-thioxo-1,3-dioxolane-4-carboxylate (959123-34-3)

Guidance literature:

With thionyl chloride; triethylamine; In dichloromethane; at 0 ℃; for 0.5h; Inert atmosphere;

DOI:10.1002/anie.201705913

Reference yield:

Methyl cinnamate (103-26-4,1754-62-7) → (4R,5S)-methyl 5-phenyl-2-thioxo-1,3-dioxolane-4-carboxylate (959123-34-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / (DHQ)2PHAL; NMO; OsO₄ / 2-methyl-propan-2-ol; H₂O / 24 h / 20 °C

2: 90 percent / thionyl chloride; triethylamine / CH₂Cl₂ / 0.75 h / 0 °C

With osmium(VIII) oxide; thionyl chloride; N-methyl-2-indolinone; Hydroquinone 1,4-phthalazinediyl diether; triethylamine; In dichloromethane; water; tert-butyl alcohol; 1: Sharpless asymmetric dihydroxylation;

DOI:10.1016/j.tetasy.2007.07.028

Reference yield: 80.0%

(4R,5S)-methyl 5-phenyl-2-thioxo-1,3-dioxolane-4-carboxylate (959123-34-3) → Methyl (2R,3R)-(-)-2-hydroxy-3-azido-3-phenyl-propionate (127053-44-5)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 80 ℃; for 48h;

DOI:10.1016/j.tetasy.2007.07.028

upstream raw materials:

methyl (2R,3S)-2,3-dihydroxy-3-phenylpropanoate

Methyl cinnamate

Downstream raw materials:

(4R,5S)-2,2-Dioxo-5-phenyl-2λ⁶-[1,3,2]dioxathiolane-4-carboxylic acid methyl ester

Methyl (2R,3R)-(-)-2-hydroxy-3-azido-3-phenyl-propionate

tert-butyl (1R,2R)-2-methoxycarbonyl-2-{[(methylthio)carbonylthioxyl]oxy}-1-phenylethylcarbamate

S-(3-hydroxy-1-phenyl-propyl)-carbamic acid tert-butyl ester