((4S,5R)-2,2,6-Trioxo-4-phenyl-1,3-dioxa-2λ⁶-thia-7-aza-spiro[4.5]dec-7-yl)-acetic acid ethyl ester

Base Information

• Chemical Name: ((4S,5R)-2,2,6-Trioxo-4-phenyl-1,3-dioxa-2λ⁶-thia-7-aza-spiro[4.5]dec-7-yl)-acetic acid ethyl ester
• CAS No.: 250248-85-2
• Molecular Formula: C₁₆H₁₉NO₇S
• Molecular Weight: 369.395

Synonyms:

Chemical Property of ((4S,5R)-2,2,6-Trioxo-4-phenyl-1,3-dioxa-2λ⁶-thia-7-aza-spiro[4.5]dec-7-yl)-acetic acid ethyl ester

Chemical Property:

Purity/Quality:

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Technology Process of ((4S,5R)-2,2,6-Trioxo-4-phenyl-1,3-dioxa-2λ⁶-thia-7-aza-spiro[4.5]dec-7-yl)-acetic acid ethyl ester

There total 7 articles about ((4S,5R)-2,2,6-Trioxo-4-phenyl-1,3-dioxa-2λ⁶-thia-7-aza-spiro[4.5]dec-7-yl)-acetic acid ethyl 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:

((4S,5R)-2,6-Dioxo-4-phenyl-1,3-dioxa-2λ4-thia-7-aza-spiro[4.5]dec-7-yl)-acetic acid ethyl ester → ((4S,5R)-2,2,6-Trioxo-4-phenyl-1,3-dioxa-2λ6-thia-7-aza-spiro[4.5]dec-7-yl)-acetic acid ethyl ester (250248-85-2)

Guidance literature:

With ruthenium trichloride; sodium periodate; In tetrachloromethane; water; acetonitrile; at 0 - 20 ℃;

DOI:10.1016/S0960-894X(99)00448-5

Reference yield:

piperidin-2-one (675-20-7) → ((4S,5R)-2,2,6-Trioxo-4-phenyl-1,3-dioxa-2λ6-thia-7-aza-spiro[4.5]dec-7-yl)-acetic acid ethyl ester (250248-85-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 80 percent / DMAP; Et₃N / CH₂Cl₂ / 0 - 20 °C

2: 33 percent / NaH; AcOH / methanol; tetrahydrofuran / 5 - 20 °C

3: 86 percent / lithium bis-trimethylsilylamide / tetrahydrofuran / 0 - 20 °C

4: 69 percent / 2 percent K₂OsO₄; AD-mix alpha; MeSO₂NH₂ / 2-methyl-propan-2-ol; H₂O / 20 °C

5: SOCl₂; Et₃N / tetrahydrofuran / 0 - 20 °C

6: NaIO₄; RuCl₃ / acetonitrile; CCl₄; H₂O / 0 - 20 °C

With dmap; ruthenium trichloride; potassium osmate(VI); sodium periodate; AD-mix-α; thionyl chloride; methanesulfonamide; sodium hydride; acetic acid; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; water; acetonitrile; tert-butyl alcohol; 1: protection / 2: Condensation / 3: Alkylation / 4: dihydroxylation / 5: sulfonylation / 6: Oxidation;

DOI:10.1016/S0960-894X(99)00448-5

Reference yield:

N-acetyl-2-piperidone (3326-13-4) → ((4S,5R)-2,2,6-Trioxo-4-phenyl-1,3-dioxa-2λ6-thia-7-aza-spiro[4.5]dec-7-yl)-acetic acid ethyl ester (250248-85-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 56 percent / NaH; AcOH / methanol; tetrahydrofuran / 5 - 20 °C

2: 86 percent / lithium bis-trimethylsilylamide / tetrahydrofuran / 0 - 20 °C

3: 69 percent / 2 percent K₂OsO₄; AD-mix alpha; MeSO₂NH₂ / 2-methyl-propan-2-ol; H₂O / 20 °C

4: SOCl₂; Et₃N / tetrahydrofuran / 0 - 20 °C

5: NaIO₄; RuCl₃ / acetonitrile; CCl₄; H₂O / 0 - 20 °C

With ruthenium trichloride; potassium osmate(VI); sodium periodate; AD-mix-α; thionyl chloride; methanesulfonamide; sodium hydride; acetic acid; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; tetrachloromethane; water; acetonitrile; tert-butyl alcohol; 1: Condensation / 2: Alkylation / 3: dihydroxylation / 4: sulfonylation / 5: Oxidation;

DOI:10.1016/S0960-894X(99)00448-5

upstream raw materials:

piperidin-2-one

N-acetyl-2-piperidone

(E)-3-phenylmethylene-2-piperidinone

2-oxopiperidine-1-carboxylic acid tert-butyl ester

Downstream raw materials:

((R)-3-Benzyl-3-hydroxy-2-oxo-piperidin-1-yl)-acetic acid ethyl ester

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