1-(2,4-Dimethoxy-benzyl)-3-[(2E,4E)-(S)-6-((1R,2R,4S,6R,7S,8S)-1,7-dimethyl-5-oxo-2-triisopropylsilanyloxymethyl-3,9,10-trioxa-tricyclo[4.3.1.0^2,4]dec-8-yl)-1-hydroxy-4-methyl-hepta-2,4-dien-(Z)-ylidene]-pyrrolidine-2,4-dione

Base Information

• Chemical Name: 1-(2,4-Dimethoxy-benzyl)-3-[(2E,4E)-(S)-6-((1R,2R,4S,6R,7S,8S)-1,7-dimethyl-5-oxo-2-triisopropylsilanyloxymethyl-3,9,10-trioxa-tricyclo[4.3.1.0^2,4]dec-8-yl)-1-hydroxy-4-methyl-hepta-2,4-dien-(Z)-ylidene]-pyrrolidine-2,4-dione
• CAS No.: 137647-83-7
• Molecular Formula: C₄₀H₅₇NO₁₀Si
• Molecular Weight: 739.979

Synonyms:1-(2,4-Dimethoxy-benzyl)-3-[(2E,4E)-(S)-6-((1R,2R,4S,6R,7S,8S)-1,7-dimethyl-5-oxo-2-triisopropylsilanyloxymethyl-3,9,10-trioxa-tricyclo[4.3.1.0^2,4]dec-8-yl)-1-hydroxy-4-methyl-hepta-2,4-dien-(Z)-ylidene]-pyrrolidine-2,4-dione

Chemical Property of 1-(2,4-Dimethoxy-benzyl)-3-[(2E,4E)-(S)-6-((1R,2R,4S,6R,7S,8S)-1,7-dimethyl-5-oxo-2-triisopropylsilanyloxymethyl-3,9,10-trioxa-tricyclo[4.3.1.0^2,4]dec-8-yl)-1-hydroxy-4-methyl-hepta-2,4-dien-(Z)-ylidene]-pyrrolidine-2,4-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of 1-(2,4-Dimethoxy-benzyl)-3-[(2E,4E)-(S)-6-((1R,2R,4S,6R,7S,8S)-1,7-dimethyl-5-oxo-2-triisopropylsilanyloxymethyl-3,9,10-trioxa-tricyclo[4.3.1.0^2,4]dec-8-yl)-1-hydroxy-4-methyl-hepta-2,4-dien-(Z)-ylidene]-pyrrolidine-2,4-dione

There total 9 articles about 1-(2,4-Dimethoxy-benzyl)-3-[(2E,4E)-(S)-6-((1R,2R,4S,6R,7S,8S)-1,7-dimethyl-5-oxo-2-triisopropylsilanyloxymethyl-3,9,10-trioxa-tricyclo[4.3.1.0^2,4]dec-8-yl)-1-hydroxy-4-methyl-hepta-2,4-dien-(Z)-ylidene]-pyrrolidine-2,4-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:

(1R,2R,4R,5S,6S,7S,8S)-8-((S)-2-Hydroxy-1-methyl-ethyl)-1,7-dimethyl-2-triisopropylsilanyloxymethyl-3,9,10-trioxa-tricyclo[4.3.1.02,4]decan-5-ol (137647-82-6) → 1-(2,4-Dimethoxy-benzyl)-3-[(2E,4E)-(S)-6-((1R,2R,4S,6R,7S,8S)-1,7-dimethyl-5-oxo-2-triisopropylsilanyloxymethyl-3,9,10-trioxa-tricyclo[4.3.1.02,4]dec-8-yl)-1-hydroxy-4-methyl-hepta-2,4-dien-(Z)-ylidene]-pyrrolidine-2,4-dione (137647-83-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 85 percent / pyridinium dichromate / CH₂Cl₂ / 7 h / Ambient temperature

2: 81 percent / CrCl₃, LAH / diethyl ether; tetrahydrofuran / 2 h / Ambient temperature

3: 85 percent / OsO₄, NaIO₄ / 2-methyl-propan-2-ol; dioxane; H₂O / 7 h / Ambient temperature

4: 75 percent / p-toluenesulfonic acid / benzene / 2 h / Heating

5: 1.) KOt-Bu / 1.) THF, 0 deg C, 2 h, 2.) THF, 0 deg C, 16 h

With chromium chloride; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; dipyridinium dichromate; potassium tert-butylate; toluene-4-sulfonic acid; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; water; tert-butyl alcohol; benzene;

DOI:10.1021/ja00023a029

Reference yield:

(1R,3S,4S,5S,6R)-3-((S)-2-Benzyloxy-1-methyl-ethyl)-1,4-dimethyl-8-triisopropylsilanyloxymethyl-2,9-dioxa-bicyclo[3.3.1]non-7-en-6-ol (137628-55-8) → 1-(2,4-Dimethoxy-benzyl)-3-[(2E,4E)-(S)-6-((1R,2R,4S,6R,7S,8S)-1,7-dimethyl-5-oxo-2-triisopropylsilanyloxymethyl-3,9,10-trioxa-tricyclo[4.3.1.02,4]dec-8-yl)-1-hydroxy-4-methyl-hepta-2,4-dien-(Z)-ylidene]-pyrrolidine-2,4-dione (137647-83-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 73 percent / m-chloroperbenzoic acid, sodium phosphate / CH₂Cl₂; H₂O / 24 h / Ambient temperature

2: 95 percent / Li, di-tert-butylbiphenyl / tetrahydrofuran / -78 °C

3: 85 percent / pyridinium dichromate / CH₂Cl₂ / 7 h / Ambient temperature

4: 81 percent / CrCl₃, LAH / diethyl ether; tetrahydrofuran / 2 h / Ambient temperature

5: 85 percent / OsO₄, NaIO₄ / 2-methyl-propan-2-ol; dioxane; H₂O / 7 h / Ambient temperature

6: 75 percent / p-toluenesulfonic acid / benzene / 2 h / Heating

7: 1.) KOt-Bu / 1.) THF, 0 deg C, 2 h, 2.) THF, 0 deg C, 16 h

With chromium chloride; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; dipyridinium dichromate; di(tert-butyl)-biphenyl; potassium tert-butylate; lithium; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; sodium phosphate; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; water; tert-butyl alcohol; benzene;

DOI:10.1021/ja00023a029

Reference yield:

(1R,2R,4R,5S,6S,7S,8S)-8-((S)-2-Benzyloxy-1-methyl-ethyl)-1,7-dimethyl-2-triisopropylsilanyloxymethyl-3,9,10-trioxa-tricyclo[4.3.1.02,4]decan-5-ol (137647-81-5) → 1-(2,4-Dimethoxy-benzyl)-3-[(2E,4E)-(S)-6-((1R,2R,4S,6R,7S,8S)-1,7-dimethyl-5-oxo-2-triisopropylsilanyloxymethyl-3,9,10-trioxa-tricyclo[4.3.1.02,4]dec-8-yl)-1-hydroxy-4-methyl-hepta-2,4-dien-(Z)-ylidene]-pyrrolidine-2,4-dione (137647-83-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 95 percent / Li, di-tert-butylbiphenyl / tetrahydrofuran / -78 °C

2: 85 percent / pyridinium dichromate / CH₂Cl₂ / 7 h / Ambient temperature

3: 81 percent / CrCl₃, LAH / diethyl ether; tetrahydrofuran / 2 h / Ambient temperature

4: 85 percent / OsO₄, NaIO₄ / 2-methyl-propan-2-ol; dioxane; H₂O / 7 h / Ambient temperature

5: 75 percent / p-toluenesulfonic acid / benzene / 2 h / Heating

6: 1.) KOt-Bu / 1.) THF, 0 deg C, 2 h, 2.) THF, 0 deg C, 16 h

With chromium chloride; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; dipyridinium dichromate; di(tert-butyl)-biphenyl; potassium tert-butylate; lithium; toluene-4-sulfonic acid; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; water; tert-butyl alcohol; benzene;

DOI:10.1021/ja00023a029

upstream raw materials:

{2-[1-(2,4-Dimethoxy-benzyl)-2,4-dioxo-pyrrolidin-(3E)-ylidene]-2-hydroxy-ethyl}-phosphonic acid diethyl ester

(E)-(S)-4-((1R,2R,4S,6R,7S,8S)-1,7-Dimethyl-5-oxo-2-triisopropylsilanyloxymethyl-3,9,10-trioxa-tricyclo[4.3.1.0^2,4]dec-8-yl)-2-methyl-pent-2-enal

(1R,2R,4R,5S,6S,7S,8S)-8-((S)-2-Hydroxy-1-methyl-ethyl)-1,7-dimethyl-2-triisopropylsilanyloxymethyl-3,9,10-trioxa-tricyclo[4.3.1.0^2,4]decan-5-ol

(R)-2-((1R,2R,4S,6R,7S,8R)-1,7-Dimethyl-5-oxo-2-triisopropylsilanyloxymethyl-3,9,10-trioxa-tricyclo[4.3.1.0^2,4]dec-8-yl)-propionaldehyde

Downstream raw materials:

(+/-)-tirandamycin B

3-[(2Z,4E)-(S)-1-Hydroxy-6-((1R,2R,4S,6R,7S,8S)-2-hydroxymethyl-1,7-dimethyl-5-oxo-3,9,10-trioxa-tricyclo[4.3.1.0^2,4]dec-8-yl)-4-methyl-hepta-2,4-dien-(E)-ylidene]-pyrrolidine-2,4-dione

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