N-(5-benzyloxy-2,3-dimethoxyxanthen-9-ylmethyl)-N-methyl-α-(methylsulfinyl)acetamide

Base Information

Chemical Name:N-(5-benzyloxy-2,3-dimethoxyxanthen-9-ylmethyl)-N-methyl-α-(methylsulfinyl)acetamide
CAS No.:154879-05-7
Molecular Formula:C₂₇H₂₉NO₆S
Molecular Weight:495.596
Hs Code.:

Synonyms:N-(5-benzyloxy-2,3-dimethoxyxanthen-9-ylmethyl)-N-methyl-α-(methylsulfinyl)acetamide

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Chemical Property of N-(5-benzyloxy-2,3-dimethoxyxanthen-9-ylmethyl)-N-methyl-α-(methylsulfinyl)acetamide

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Technology Process of N-(5-benzyloxy-2,3-dimethoxyxanthen-9-ylmethyl)-N-methyl-α-(methylsulfinyl)acetamide

There total 16 articles about N-(5-benzyloxy-2,3-dimethoxyxanthen-9-ylmethyl)-N-methyl-α-(methylsulfinyl)acetamide 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:

: 6272-38-4
O-benzylcatechol

: 154879-05-7
N-(5-benzyloxy-2,3-dimethoxyxanthen-9-ylmethyl)-N-methyl-α-(methylsulfinyl)acetamide

Guidance literature:: Multi-step reaction with 11 steps

1: 61 percent / K₂CO₃, CuO / pyridine / 20 h / Heating

2: 76 percent / 1.) LDA; 2.) HMPA / hexane; tetrahydrofuran / 1.) -78 deg C, 30 min; 2.) -78 deg C, 30 min; 3.) RT, 1 h

3: 91 percent / NaIO₄ / H₂O; acetone / 15 h / Ambient temperature

4: 38 percent / trifluoroacetic anhydride (TFAA) / CH₂Cl₂ / 24 h / Ambient temperature

5: 66 percent / SnCl₄ / CH₂Cl₂ / 1.) 0 deg C, 1 h; 2.) RT, 6 h

6: 86 percent / H₂ / 5percent Pd/C / methanol / 168 h / at 6 kg/cm²

7: 92 percent / K₂CO₃ / acetone / 2 h / Heating

8: 92 percent / methanol / 5 h / 95 °C / sealed tube

9: BH₃*THF / 240 h / Heating

10: Et₃N / CH₂Cl₂ / 9 h / Ambient temperature

11: NAIO₄ / H₂O; methanol / 60 h / Ambient temperature

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium periodate; borane-THF; hydrogen; tin(IV) chloride; potassium carbonate; triethylamine; trifluoroacetic anhydride; copper(II) oxide; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; hexane; dichloromethane; water; acetone;
DOI:10.1016/S0040-4020(01)81754-3

Reference yield:

: 2859-78-1
4-Bromoveratrole

: 154879-05-7
N-(5-benzyloxy-2,3-dimethoxyxanthen-9-ylmethyl)-N-methyl-α-(methylsulfinyl)acetamide

Guidance literature:: Multi-step reaction with 13 steps

1: 98 percent / SnCl₄ / CH₂Cl₂ / 0.5 h / Ambient temperature

2: 96 percent / Zn / acetic acid / 5 h / Heating

3: 61 percent / K₂CO₃, CuO / pyridine / 20 h / Heating

4: 76 percent / 1.) LDA; 2.) HMPA / hexane; tetrahydrofuran / 1.) -78 deg C, 30 min; 2.) -78 deg C, 30 min; 3.) RT, 1 h

5: 91 percent / NaIO₄ / H₂O; acetone / 15 h / Ambient temperature

6: 38 percent / trifluoroacetic anhydride (TFAA) / CH₂Cl₂ / 24 h / Ambient temperature

7: 66 percent / SnCl₄ / CH₂Cl₂ / 1.) 0 deg C, 1 h; 2.) RT, 6 h

8: 86 percent / H₂ / 5percent Pd/C / methanol / 168 h / at 6 kg/cm²

9: 92 percent / K₂CO₃ / acetone / 2 h / Heating

10: 92 percent / methanol / 5 h / 95 °C / sealed tube

11: BH₃*THF / 240 h / Heating

12: Et₃N / CH₂Cl₂ / 9 h / Ambient temperature

13: NAIO₄ / H₂O; methanol / 60 h / Ambient temperature

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium periodate; borane-THF; hydrogen; tin(IV) chloride; potassium carbonate; triethylamine; trifluoroacetic anhydride; copper(II) oxide; zinc; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; hexane; dichloromethane; water; acetic acid; acetone;
DOI:10.1016/S0040-4020(01)81754-3

Reference yield:

: 154878-95-2
ethyl 2-<2-(benzyloxy)phenoxy>-4,5-dimethoxyphenylacetate

: 154879-05-7
N-(5-benzyloxy-2,3-dimethoxyxanthen-9-ylmethyl)-N-methyl-α-(methylsulfinyl)acetamide

Guidance literature:: Multi-step reaction with 10 steps

1: 76 percent / 1.) LDA; 2.) HMPA / hexane; tetrahydrofuran / 1.) -78 deg C, 30 min; 2.) -78 deg C, 30 min; 3.) RT, 1 h

2: 91 percent / NaIO₄ / H₂O; acetone / 15 h / Ambient temperature

3: 38 percent / trifluoroacetic anhydride (TFAA) / CH₂Cl₂ / 24 h / Ambient temperature

4: 66 percent / SnCl₄ / CH₂Cl₂ / 1.) 0 deg C, 1 h; 2.) RT, 6 h

5: 86 percent / H₂ / 5percent Pd/C / methanol / 168 h / at 6 kg/cm²

6: 92 percent / K₂CO₃ / acetone / 2 h / Heating

7: 92 percent / methanol / 5 h / 95 °C / sealed tube

8: BH₃*THF / 240 h / Heating

9: Et₃N / CH₂Cl₂ / 9 h / Ambient temperature

10: NAIO₄ / H₂O; methanol / 60 h / Ambient temperature

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium periodate; borane-THF; hydrogen; tin(IV) chloride; potassium carbonate; triethylamine; trifluoroacetic anhydride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; water; acetone;
DOI:10.1016/S0040-4020(01)81754-3