(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

Base Information

• Chemical Name: (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
• CAS No.: 132277-60-2
• Molecular Formula: C₃₉H₄₄N₂O₈
• Molecular Weight: 668.787

Synonyms:

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 11 articles about (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 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:

5-(benzyloxy)-2,4-dimethoxy-3-methylbenzaldehyde (82622-02-4) → (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[7.3.1.02,7]trideca-2,4,6-trien-10-one (132277-60-2)

Guidance literature:

Multi-step reaction with 11 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

With 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; Raney nickel W₂; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

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

Reference yield:

(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[7.3.1.02,7]trideca-2,4,6-triene-13-carboxylic acid benzyl ester (132277-56-6) → (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[7.3.1.02,7]trideca-2,4,6-trien-10-one (132277-60-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 70 percent / H₂ / Raney Nickel W₂ / ethanol / 80 °C / 62057.8 Torr

2: PhNMe₂ / CH₂Cl₂ / 23 °C

3: K₂CO₃ / dimethylformamide / 23 °C

4: 78 percent / Swern oxidation

5: DDQ, water / tetrahydrofuran / 23 °C

6: K₂CO₃ / dimethylformamide / 23 °C

7: DBU / methanol / 23 °C

8: NaBH₃CN, TFA / methanol / 23 °C

With 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; Raney nickel W₂; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

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

Reference yield:

4-Acetyl-2-(4-{3-[diphenyl-(1,1,2-trimethyl-propyl)-silanyloxy]-propoxy}-2-methoxy-5-methoxymethoxy-3-methyl-benzyl)-3,6-dioxo-piperazine-1-carboxylic acid benzyl ester → (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[7.3.1.02,7]trideca-2,4,6-trien-10-one (132277-60-2)

Guidance literature:

Multi-step reaction with 11 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

With 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; Raney nickel W₂; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

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

upstream raw materials:

formaldehyd

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

(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

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

Downstream raw materials:

(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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