(1R,8S,9R,12S)-12-(5-Hydroxy-2,4-dimethoxy-3-methyl-benzyl)-4,6-dimethoxy-5,13-dimethyl-11,13-diaza-tricyclo[7.3.1.0^2,7]trideca-2,4,6-triene-3,8-diol

Base Information

• Chemical Name: (1R,8S,9R,12S)-12-(5-Hydroxy-2,4-dimethoxy-3-methyl-benzyl)-4,6-dimethoxy-5,13-dimethyl-11,13-diaza-tricyclo[7.3.1.0^2,7]trideca-2,4,6-triene-3,8-diol
• CAS No.: 132277-61-3
• Molecular Formula: C₂₅H₃₄N₂O₇
• Molecular Weight: 474.554

Synonyms:(1R,8S,9R,12S)-12-(5-Hydroxy-2,4-dimethoxy-3-methyl-benzyl)-4,6-dimethoxy-5,13-dimethyl-11,13-diaza-tricyclo[7.3.1.0^2,7]trideca-2,4,6-triene-3,8-diol

Chemical Property of (1R,8S,9R,12S)-12-(5-Hydroxy-2,4-dimethoxy-3-methyl-benzyl)-4,6-dimethoxy-5,13-dimethyl-11,13-diaza-tricyclo[7.3.1.0^2,7]trideca-2,4,6-triene-3,8-diol

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Technology Process of (1R,8S,9R,12S)-12-(5-Hydroxy-2,4-dimethoxy-3-methyl-benzyl)-4,6-dimethoxy-5,13-dimethyl-11,13-diaza-tricyclo[7.3.1.0^2,7]trideca-2,4,6-triene-3,8-diol

There total 14 articles about (1R,8S,9R,12S)-12-(5-Hydroxy-2,4-dimethoxy-3-methyl-benzyl)-4,6-dimethoxy-5,13-dimethyl-11,13-diaza-tricyclo[7.3.1.0^2,7]trideca-2,4,6-triene-3,8-diol 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:

(1R,8S,9R,12S)-3-Benzyloxy-12-(5-benzyloxy-2,4-dimethoxy-3-methyl-benzyl)-4,6-dimethoxy-5,13-dimethyl-11,13-diaza-tricyclo[7.3.1.02,7]trideca-2,4,6-trien-8-ol → (1R,8S,9R,12S)-12-(5-Hydroxy-2,4-dimethoxy-3-methyl-benzyl)-4,6-dimethoxy-5,13-dimethyl-11,13-diaza-tricyclo[7.3.1.02,7]trideca-2,4,6-triene-3,8-diol (132277-61-3)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; at 23 ℃; Yield given;

DOI:10.1016/S0040-4039(00)98010-9

Reference yield:

5-(benzyloxy)-2,4-dimethoxy-3-methylbenzaldehyde (82622-02-4) → (1R,8S,9R,12S)-12-(5-Hydroxy-2,4-dimethoxy-3-methyl-benzyl)-4,6-dimethoxy-5,13-dimethyl-11,13-diaza-tricyclo[7.3.1.02,7]trideca-2,4,6-triene-3,8-diol (132277-61-3)

Guidance literature:

Multi-step reaction with 13 steps

1: 1) t-BuOK 2) DBU / 1) THF, -78 deg C 2) 0 deg C

2: NaBH₄, AcOH / ethanol / 0 °C

3: 1) HCO₂H 2) NaOH / 1) 55 deg C 2) MeOH, 23 deg C

4: 70 percent / H₂ / Raney Nickel W₂ / ethanol / 80 °C / 62057.8 Torr

5: PhNMe₂ / CH₂Cl₂ / 23 °C

6: K₂CO₃ / dimethylformamide / 23 °C

7: 78 percent / Swern oxidation

8: DDQ, water / tetrahydrofuran / 23 °C

9: K₂CO₃ / dimethylformamide / 23 °C

10: DBU / methanol / 23 °C

11: NaBH₃CN, TFA / methanol / 23 °C

12: AlH₃ / tetrahydrofuran / 23 °C

13: H₂ / Pd/C / ethanol / 23 °C

With aluminium hydride; sodium hydroxide; sodium tetrahydroborate; formic acid; potassium tert-butylate; water; hydrogen; sodium cyanoborohydride; potassium carbonate; acetic acid; N,N-dimethyl-aniline; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; Raney nickel W₂; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)98010-9

Reference yield:

(1S,9R,12R)-3-Hydroxy-12-(5-hydroxy-2,4-dimethoxy-3-methyl-benzyl)-4-(3-hydroxy-propoxy)-6-methoxy-5-methyl-11,13-diaza-tricyclo[7.3.1.02,7]trideca-2,4,6-trien-10-one (132277-57-7) → (1R,8S,9R,12S)-12-(5-Hydroxy-2,4-dimethoxy-3-methyl-benzyl)-4,6-dimethoxy-5,13-dimethyl-11,13-diaza-tricyclo[7.3.1.02,7]trideca-2,4,6-triene-3,8-diol (132277-61-3)

Guidance literature:

Multi-step reaction with 9 steps

1: PhNMe₂ / CH₂Cl₂ / 23 °C

2: K₂CO₃ / dimethylformamide / 23 °C

3: 78 percent / Swern oxidation

4: DDQ, water / tetrahydrofuran / 23 °C

5: K₂CO₃ / dimethylformamide / 23 °C

6: DBU / methanol / 23 °C

7: NaBH₃CN, TFA / methanol / 23 °C

8: AlH₃ / tetrahydrofuran / 23 °C

9: H₂ / Pd/C / ethanol / 23 °C

With aluminium hydride; water; hydrogen; sodium cyanoborohydride; potassium carbonate; N,N-dimethyl-aniline; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)98010-9

upstream raw materials:

5-(benzyloxy)-2,4-dimethoxy-3-methylbenzaldehyde

(1S,9R,12R)-3-Hydroxy-12-(5-hydroxy-2,4-dimethoxy-3-methyl-benzyl)-4-(3-hydroxy-propoxy)-6-methoxy-5-methyl-11,13-diaza-tricyclo[7.3.1.0^2,7]trideca-2,4,6-trien-10-one

(1R,8S,9S,12S)-3-Benzyloxy-12-(5-benzyloxy-2,4-dimethoxy-3-methyl-benzyl)-8-hydroxy-4,6-dimethoxy-5,13-dimethyl-11,13-diaza-tricyclo[7.3.1.0^2,7]trideca-2,4,6-trien-10-one

(1R,9S)-12-[1-(5-Benzyloxy-2,4-dimethoxy-3-methyl-phenyl)-meth-(Z)-ylidene]-3-hydroxy-4-(3-hydroxy-propoxy)-6-methoxy-5-methyl-10-oxo-11,13-diaza-tricyclo[7.3.1.0^2,7]trideca-2,4,6-triene-13-carboxylic acid benzyl ester

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