[1-benzyl-2-(2-benzyl-1,1-dioxo-1λ⁶-isothiazolidin-5-ylidene)-ethyl]-carbamic acid tert-butyl ester

Base Information

• Chemical Name: [1-benzyl-2-(2-benzyl-1,1-dioxo-1λ⁶-isothiazolidin-5-ylidene)-ethyl]-carbamic acid tert-butyl ester
• CAS No.: 905975-39-5
• Molecular Formula: C₂₄H₃₀N₂O₄S
• Molecular Weight: 442.579

Synonyms:[1-benzyl-2-(2-benzyl-1,1-dioxo-1λ⁶-isothiazolidin-5-ylidene)-ethyl]-carbamic acid tert-butyl ester

Chemical Property of [1-benzyl-2-(2-benzyl-1,1-dioxo-1λ⁶-isothiazolidin-5-ylidene)-ethyl]-carbamic acid tert-butyl ester

Chemical Property:

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Technology Process of [1-benzyl-2-(2-benzyl-1,1-dioxo-1λ⁶-isothiazolidin-5-ylidene)-ethyl]-carbamic acid tert-butyl ester

There total 4 articles about [1-benzyl-2-(2-benzyl-1,1-dioxo-1λ⁶-isothiazolidin-5-ylidene)-ethyl]-carbamic acid tert-butyl 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: 58.0%

(2-benzyl-1,1-dioxo-1λ6-isothiazolidin-5-yl)-phosphonic acid diethyl ester (905975-31-7) + Boc-L-phenylalaninal (72155-45-4) → [1-benzyl-2-(2-benzyl-1,1-dioxo-1λ6-isothiazolidin-5-ylidene)-ethyl]-carbamic acid tert-butyl ester (905975-39-5) + [1-benzyl-2-(2-benzyl-1,1-dioxo-1λ6-isothiazolidin-5-ylidene)-ethyl]-carbamic acid tert-butyl ester (905975-35-1)

Guidance literature:

(2-benzyl-1,1-dioxo-1λ⁶-isothiazolidin-5-yl)-phosphonic acid diethyl ester; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 20 ℃;

Boc-L-phenylalaninal; In tetrahydrofuran; hexane;

DOI:10.1016/j.bmcl.2006.04.079

Reference yield:

N-benzyl-3-chloropropane-1-sulfonamide (90945-14-5) → [1-benzyl-2-(2-benzyl-1,1-dioxo-1λ6-isothiazolidin-5-ylidene)-ethyl]-carbamic acid tert-butyl ester (905975-39-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaOH; TEA / CH₂Cl₂ / Heating

2.1: LDA / hexane; tetrahydrofuran / -78 °C

2.2: 43 percent / tetrahydrofuran; hexane / -78 °C

3.1: n-BuLi / hexane; tetrahydrofuran / -78 - 20 °C

3.2: 29 percent / tetrahydrofuran; hexane

With sodium hydroxide; n-butyllithium; TEA; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; 2.2: Wittig-Horner reaction / 3.2: Wittig-Horner reacton;

DOI:10.1016/j.bmcl.2006.04.079

Reference yield:

2-benzylisothiazolidine 1,1-dioxide (91818-96-1) → [1-benzyl-2-(2-benzyl-1,1-dioxo-1λ6-isothiazolidin-5-ylidene)-ethyl]-carbamic acid tert-butyl ester (905975-39-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: LDA / hexane; tetrahydrofuran / -78 °C

1.2: 43 percent / tetrahydrofuran; hexane / -78 °C

2.1: n-BuLi / hexane; tetrahydrofuran / -78 - 20 °C

2.2: 29 percent / tetrahydrofuran; hexane

With n-butyllithium; lithium diisopropyl amide; In tetrahydrofuran; hexane; 1.2: Wittig-Horner reaction / 2.2: Wittig-Horner reacton;

DOI:10.1016/j.bmcl.2006.04.079

upstream raw materials:

(2-benzyl-1,1-dioxo-1λ⁶-isothiazolidin-5-yl)-phosphonic acid diethyl ester

Boc-L-phenylalaninal

N-benzyl-3-chloropropane-1-sulfonamide

2-benzylisothiazolidine 1,1-dioxide

Downstream raw materials:

((S)-1-{(S)-1-Benzyl-2-[2-benzyl-1,1-dioxo-1λ⁶-isothiazolidin-(5Z)-ylidene]-ethylcarbamoyl}-3-methyl-butyl)-carbamic acid tert-butyl ester

(S)-1-Benzyl-2-[2-benzyl-1,1-dioxo-1λ⁶-isothiazolidin-(5Z)-ylidene]-ethylamine

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