(-)-N-[2-(1,3-dioxo-1λ⁴,3λ⁴-dithian-2-ylidene)ethyl]-N-(2,2-dimethoxyethyl)carbamic acid benzyl ester

Base Information

• Chemical Name: (-)-N-[2-(1,3-dioxo-1λ⁴,3λ⁴-dithian-2-ylidene)ethyl]-N-(2,2-dimethoxyethyl)carbamic acid benzyl ester
• CAS No.: 569682-63-9
• Molecular Formula: C₁₈H₂₅NO₆S₂
• Molecular Weight: 415.532

Synonyms:(-)-N-[2-(1,3-dioxo-1λ⁴,3λ⁴-dithian-2-ylidene)ethyl]-N-(2,2-dimethoxyethyl)carbamic acid benzyl ester

Chemical Property of (-)-N-[2-(1,3-dioxo-1λ⁴,3λ⁴-dithian-2-ylidene)ethyl]-N-(2,2-dimethoxyethyl)carbamic acid benzyl ester

Chemical Property:

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Technology Process of (-)-N-[2-(1,3-dioxo-1λ⁴,3λ⁴-dithian-2-ylidene)ethyl]-N-(2,2-dimethoxyethyl)carbamic acid benzyl ester

There total 3 articles about (-)-N-[2-(1,3-dioxo-1λ⁴,3λ⁴-dithian-2-ylidene)ethyl]-N-(2,2-dimethoxyethyl)carbamic 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: 71.0%

(+)-diethyl [(1R,3R)-1,3-dioxo-1,3-dithian-2-yl]phosphonate (214899-24-8) + N-(2,2-dimethoxyethyl)-N-(2-oxoethyl) carbamic acid benzyl ester (569682-62-8) → (-)-N-[2-(1,3-dioxo-1λ4,3λ4-dithian-2-ylidene)ethyl]-N-(2,2-dimethoxyethyl)carbamic acid benzyl ester (569682-63-9)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; at 70 ℃; for 4h;

DOI:10.1039/b212719a

Reference yield:

benzyl N-(2,2-dimethoxyethyl)carbamate (114790-39-5) → (-)-N-[2-(1,3-dioxo-1λ4,3λ4-dithian-2-ylidene)ethyl]-N-(2,2-dimethoxyethyl)carbamic acid benzyl ester (569682-63-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaH / dimethylformamide / 25 °C

1.2: 72 percent / dimethylformamide / 15 h / 20 °C

2.1: O₃ / CH₂Cl₂ / 0.5 h / -78 °C

2.2: 60 percent / Me₂S / dimethylformamide / 3 h / 20 °C

3.1: 71 percent / LiOH*H₂O / tetrahydrofuran / 4 h / 70 °C

With lithium hydroxide; sodium hydride; ozone; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 3.1: Horner-Wadsworth-Emmons olefination;

DOI:10.1039/b212719a

Reference yield:

benzyl N-(2,2-dimethoxyethyl)-N-(prop-2-en-1-yl)carbamate (569682-60-6) → (-)-N-[2-(1,3-dioxo-1λ4,3λ4-dithian-2-ylidene)ethyl]-N-(2,2-dimethoxyethyl)carbamic acid benzyl ester (569682-63-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: O₃ / CH₂Cl₂ / 0.5 h / -78 °C

1.2: 60 percent / Me₂S / dimethylformamide / 3 h / 20 °C

2.1: 71 percent / LiOH*H₂O / tetrahydrofuran / 4 h / 70 °C

With lithium hydroxide; ozone; In tetrahydrofuran; dichloromethane; 2.1: Horner-Wadsworth-Emmons olefination;

DOI:10.1039/b212719a

upstream raw materials:

(+)-diethyl [(1R,3R)-1,3-dioxo-1,3-dithian-2-yl]phosphonate

N-(2,2-dimethoxyethyl)-N-(2-oxoethyl) carbamic acid benzyl ester

benzyl N-(2,2-dimethoxyethyl)carbamate

benzyl N-(2,2-dimethoxyethyl)-N-(prop-2-en-1-yl)carbamate

Downstream raw materials:

(+)-cis-(4S,3R)-4-benzylaminopyrrolidine-1,3-dicarboxylic acid-1-benzyl ester

(3R,4R)-4-aminopyrrolidine-3-carboxylic acid

(+)-[1'R,3'R]-1-benzyl-1',3'-dioxospiro[1',3'-dithiane-2',3-pyrrolo[3,4-c]isoxazole]-5-carboxylic acid benzyl ester

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