(4R,5S)-4,5-Dimethyl-2,2-dioxo-2λ⁶-[1,3,2]dioxathiolane-4-carboxylic acid benzyl ester

Base Information

• Chemical Name: (4R,5S)-4,5-Dimethyl-2,2-dioxo-2λ⁶-[1,3,2]dioxathiolane-4-carboxylic acid benzyl ester
• CAS No.: 211805-80-0
• Molecular Formula: C₁₂H₁₄O₆S
• Molecular Weight: 286.306

Synonyms:(4R,5S)-4,5-Dimethyl-2,2-dioxo-2λ⁶-[1,3,2]dioxathiolane-4-carboxylic acid benzyl ester

Chemical Property of (4R,5S)-4,5-Dimethyl-2,2-dioxo-2λ⁶-[1,3,2]dioxathiolane-4-carboxylic acid benzyl ester

Chemical Property:

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Technology Process of (4R,5S)-4,5-Dimethyl-2,2-dioxo-2λ⁶-[1,3,2]dioxathiolane-4-carboxylic acid benzyl ester

There total 3 articles about (4R,5S)-4,5-Dimethyl-2,2-dioxo-2λ⁶-[1,3,2]dioxathiolane-4-carboxylic acid benzyl 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)-4,5-Dimethyl-2-oxo-2λ4-[1,3,2]dioxathiolane-4-carboxylic acid benzyl ester → (4R,5S)-4,5-Dimethyl-2,2-dioxo-2λ6-[1,3,2]dioxathiolane-4-carboxylic acid benzyl ester (211805-80-0)

Guidance literature:

With ruthenium trichloride; sodium periodate; In tetrachloromethane; water; acetonitrile; at 40 ℃; for 3h; Yield given;

DOI:10.1021/jo971983u

Reference yield:

benzyl tiglate (37526-88-8) → (4R,5S)-4,5-Dimethyl-2,2-dioxo-2λ6-[1,3,2]dioxathiolane-4-carboxylic acid benzyl ester (211805-80-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / AD-mix α, methanesulfonamide / 2-methyl-propan-2-ol; H2O / 48 h / 4 °C

2: SOCl₂ / CH₂Cl₂ / 2.5 h / 40 °C

3: NaIO₄, RuCl₃ hydrate / acetonitrile; CCl₄; H₂O / 3 h / 40 °C

With ruthenium trichloride; sodium periodate; AD-mix-α; thionyl chloride; methanesulfonamide; In tetrachloromethane; dichloromethane; water; acetonitrile; tert-butyl alcohol;

DOI:10.1021/jo971983u

Reference yield:

benzyl (2R,3S)-2,3-dihydroxy-2-methylbutanoate (211805-79-7) → (4R,5S)-4,5-Dimethyl-2,2-dioxo-2λ6-[1,3,2]dioxathiolane-4-carboxylic acid benzyl ester (211805-80-0)

Guidance literature:

Multi-step reaction with 2 steps

1: SOCl₂ / CH₂Cl₂ / 2.5 h / 40 °C

2: NaIO₄, RuCl₃ hydrate / acetonitrile; CCl₄; H₂O / 3 h / 40 °C

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

DOI:10.1021/jo971983u

upstream raw materials:

benzyl tiglate

benzyl (2R,3S)-2,3-dihydroxy-2-methylbutanoate

Downstream raw materials:

(2S,3R)-2,3-Dimethyl-aziridine-1,2-dicarboxylic acid dibenzyl ester

(2S,3R)-2,3-dimethylaziridine-2-carboxylic acid benzyl ester

(2S,3S)-α-methylthreonine

(2S,3S)-2-Azido-3-hydroxy-2-methyl-butyric acid benzyl ester

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