(1S,3R,5S)-1-Benzyloxymethyl-6-(2-chloromethyl-6-methoxy-phenyl)-3-(4-methoxy-phenyl)-8-methyl-2,4-dithia-6,8-diaza-bicyclo[3.2.2]nonane-7,9-dione

Base Information

• Chemical Name: (1S,3R,5S)-1-Benzyloxymethyl-6-(2-chloromethyl-6-methoxy-phenyl)-3-(4-methoxy-phenyl)-8-methyl-2,4-dithia-6,8-diaza-bicyclo[3.2.2]nonane-7,9-dione
• CAS No.: 79247-65-7
• Molecular Formula: C₂₉H₂₉ClN₂O₅S₂
• Molecular Weight: 585.145

Synonyms:(1S,3R,5S)-1-Benzyloxymethyl-6-(2-chloromethyl-6-methoxy-phenyl)-3-(4-methoxy-phenyl)-8-methyl-2,4-dithia-6,8-diaza-bicyclo[3.2.2]nonane-7,9-dione

Chemical Property of (1S,3R,5S)-1-Benzyloxymethyl-6-(2-chloromethyl-6-methoxy-phenyl)-3-(4-methoxy-phenyl)-8-methyl-2,4-dithia-6,8-diaza-bicyclo[3.2.2]nonane-7,9-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3R,5S)-1-Benzyloxymethyl-6-(2-chloromethyl-6-methoxy-phenyl)-3-(4-methoxy-phenyl)-8-methyl-2,4-dithia-6,8-diaza-bicyclo[3.2.2]nonane-7,9-dione

There total 11 articles about (1S,3R,5S)-1-Benzyloxymethyl-6-(2-chloromethyl-6-methoxy-phenyl)-3-(4-methoxy-phenyl)-8-methyl-2,4-dithia-6,8-diaza-bicyclo[3.2.2]nonane-7,9-dione 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: 72.5%

Benzyloxymethyl chloride (3587-60-8) + (1R,3R,5R)-6-(2-Chloromethyl-6-methoxy-phenyl)-3-(4-methoxy-phenyl)-8-methyl-2,4-dithia-6,8-diaza-bicyclo[3.2.2]nonane-7,9-dione (49593-04-6,49593-05-7,50763-59-2,50763-60-5) → (1S,3R,5S)-1-Benzyloxymethyl-6-(2-chloromethyl-6-methoxy-phenyl)-3-(4-methoxy-phenyl)-8-methyl-2,4-dithia-6,8-diaza-bicyclo[3.2.2]nonane-7,9-dione (79247-65-7)

Guidance literature:

With phenyllithium; In tetrahydrofuran; at -78 ℃; for 0.166667h;

DOI:10.1016/S0040-4020(01)97960-8

Reference yield:

1-methylpiperazin-2,5-dione (5625-52-5) → (1S,3R,5S)-1-Benzyloxymethyl-6-(2-chloromethyl-6-methoxy-phenyl)-3-(4-methoxy-phenyl)-8-methyl-2,4-dithia-6,8-diaza-bicyclo[3.2.2]nonane-7,9-dione (79247-65-7)

Guidance literature:

Multi-step reaction with 11 steps

1: CuI, K₂CO₃ / nitrobenzene / 0.67 h / 170 °C

2: methanol; diethyl ether / Ambient temperature

3: NBS, benzoylperoxide / CCl₄ / 1.5 h / Heating

4: CH₂Cl₂ / Ambient temperature

5: HCl / methanol / 0.67 h / 50 °C

6: BF₃ etherate / CH₂Cl₂ / Ambient temperature

7: 1N NaOH / dioxane / 3 h / Ambient temperature

8: Et₃N / CH₂Cl₂ / 10 h / Ambient temperature

9: NaBH₄ / methanol; CH₂Cl₂ / 0.08 h / 0 °C

10: 1.) CH₃SO₂Cl, Et₃N; 2.) LiCl / 1.) CH₂Cl₂, r.t. 10 min; 2.) DMF, r.t., 15 min.

11: 72.5 percent / phenyllithium / tetrahydrofuran / 0.17 h / -78 °C

With hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; copper(l) iodide; Perbenzoic acid; boron trifluoride diethyl etherate; potassium carbonate; methanesulfonyl chloride; phenyllithium; triethylamine; lithium chloride; In tetrahydrofuran; 1,4-dioxane; methanol; tetrachloromethane; diethyl ether; dichloromethane; nitrobenzene;

DOI:10.1016/S0040-4020(01)97960-8

Reference yield:

2-iodo-3-methoxybenzoic acid (50627-31-1) → (1S,3R,5S)-1-Benzyloxymethyl-6-(2-chloromethyl-6-methoxy-phenyl)-3-(4-methoxy-phenyl)-8-methyl-2,4-dithia-6,8-diaza-bicyclo[3.2.2]nonane-7,9-dione (79247-65-7)

Guidance literature:

Multi-step reaction with 11 steps

1: CuI, K₂CO₃ / nitrobenzene / 0.67 h / 170 °C

2: methanol; diethyl ether / Ambient temperature

3: NBS, benzoylperoxide / CCl₄ / 1.5 h / Heating

4: CH₂Cl₂ / Ambient temperature

5: HCl / methanol / 0.67 h / 50 °C

6: BF₃ etherate / CH₂Cl₂ / Ambient temperature

7: 1N NaOH / dioxane / 3 h / Ambient temperature

8: Et₃N / CH₂Cl₂ / 10 h / Ambient temperature

9: NaBH₄ / methanol; CH₂Cl₂ / 0.08 h / 0 °C

10: 1.) CH₃SO₂Cl, Et₃N; 2.) LiCl / 1.) CH₂Cl₂, r.t. 10 min; 2.) DMF, r.t., 15 min.

11: 72.5 percent / phenyllithium / tetrahydrofuran / 0.17 h / -78 °C

With hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; copper(l) iodide; Perbenzoic acid; boron trifluoride diethyl etherate; potassium carbonate; methanesulfonyl chloride; phenyllithium; triethylamine; lithium chloride; In tetrahydrofuran; 1,4-dioxane; methanol; tetrachloromethane; diethyl ether; dichloromethane; nitrobenzene;

DOI:10.1016/S0040-4020(01)97960-8

upstream raw materials:

Benzyloxymethyl chloride

(1R,3R,5R)-6-(2-Chloromethyl-6-methoxy-phenyl)-3-(4-methoxy-phenyl)-8-methyl-2,4-dithia-6,8-diaza-bicyclo[3.2.2]nonane-7,9-dione

1-methylpiperazin-2,5-dione

2-iodo-3-methoxybenzoic acid

Downstream raw materials:

C₂₉H₂₈N₂O₅S₂

C₂₁H₂₀N₂O₅S₂

dl-dehydrogliotoxin

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