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

Base Information

• Chemical Name: (4R,5S)-2,2-Dioxo-5-phenyl-2λ⁶-[1,3,2]dioxathiolane-4-carboxylic acid methyl ester
• CAS No.: 154460-20-5
• Molecular Formula: C₁₀H₁₀O₆S
• Molecular Weight: 258.252

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

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

Chemical Property:

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

There total 3 articles about (4R,5S)-2,2-Dioxo-5-phenyl-2λ⁶-[1,3,2]dioxathiolane-4-carboxylic acid methyl 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:

(4R,5S)-methyl 5-phenyl-2-thioxo-1,3-dioxolane-4-carboxylate (959123-34-3) → (4R,5S)-2,2-Dioxo-5-phenyl-2λ6-[1,3,2]dioxathiolane-4-carboxylic acid methyl ester (154460-20-5)

Guidance literature:

With ruthenium trichloride; sodium periodate; In tetrachloromethane; acetonitrile; Yield given;

DOI:10.1039/c39940000021

Reference yield:

methyl (2R,3S)-2,3-dihydroxy-3-phenylpropanoate (122743-18-4) → (4R,5S)-2,2-Dioxo-5-phenyl-2λ6-[1,3,2]dioxathiolane-4-carboxylic acid methyl ester (154460-20-5)

Guidance literature:

Multi-step reaction with 2 steps

1: SOCl₂ / CCl₄

2: RuCl₃, NaIO₄ / CCl₄; acetonitrile

With ruthenium trichloride; sodium periodate; thionyl chloride; In tetrachloromethane; acetonitrile;

DOI:10.1039/c39940000021

Reference yield:

Methyl cinnamate (103-26-4,1754-62-7) → (4R,5S)-2,2-Dioxo-5-phenyl-2λ6-[1,3,2]dioxathiolane-4-carboxylic acid methyl ester (154460-20-5)

Guidance literature:

Multi-step reaction with 3 steps

1: AD-mix-α

2: SOCl₂ / CCl₄

3: RuCl₃, NaIO₄ / CCl₄; acetonitrile

With ruthenium trichloride; sodium periodate; AD-mix-α; thionyl chloride; In tetrachloromethane; acetonitrile;

DOI:10.1039/c39940000021

upstream raw materials:

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

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

Methyl cinnamate

Downstream raw materials:

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

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

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