Tirandamycin B

Base Information

• Chemical Name: Tirandamycin B
• CAS No.: 60587-14-6
• Molecular Formula: C22H27NO8
• Molecular Weight: 433.4517
• Mol file: 60587-14-6.mol

Synonyms:2,4-Pyrrolidinedione,3-(1-hydroxy-6-(2-(hydroxymethyl)-1,7-dimethyl-5-oxo-3,9,10-trioxatricyclo(4.3.1.0(2,4))dec-8-yl)-4-methyl-2,4-heptadienylidene)-,(1S-(1alpha,2beta,4beta,6alpha,7beta,8alpha(1S*,2E,4E,6E)));

Chemical Property of Tirandamycin B

Chemical Property:

• Vapor Pressure: 3.33E-17mmHg at 25°C
• Boiling Point: 605.8°Cat760mmHg
• Flash Point: 320.2°C
• PSA: 138.18000
• Density: 1.371g/cm³
• LogP: 0.76080

Purity/Quality:

99% ^*data from raw suppliers

TirandamycinB ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Tirandamycin B

There total 22 articles about Tirandamycin B 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:

3-[(2Z,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-(E)-ylidene]-pyrrolidine-2,4-dione (137628-60-5) → 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[4.3.1.02,4]dec-8-yl)-4-methyl-hepta-2,4-dien-(E)-ylidene]-pyrrolidine-2,4-dione (60587-14-6,137694-62-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 21h; Ambient temperature;

DOI:10.1021/ja00023a029

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) → 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[4.3.1.02,4]dec-8-yl)-4-methyl-hepta-2,4-dien-(E)-ylidene]-pyrrolidine-2,4-dione (60587-14-6,137694-62-3)

Guidance literature:

Multi-step reaction with 7 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

6: 98 percent / CF₃COOH / 0.08 h / Ambient temperature

7: tetrabutylammonium fluoride / tetrahydrofuran / 21 h / Ambient temperature

With chromium chloride; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; dipyridinium dichromate; potassium tert-butylate; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; trifluoroacetic acid; 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-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) → (+/-)-tirandamycin B (60587-14-6,137694-62-3)

Guidance literature:

Multi-step reaction with 8 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

6: 98 percent / CF₃COOH / 0.08 h / Ambient temperature

7: tetrabutylammonium fluoride / tetrahydrofuran / 21 h / Ambient temperature

8: toluene / Heating

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

DOI:10.1021/ja00023a029

upstream raw materials:

3-[(2Z,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-(E)-ylidene]-pyrrolidine-2,4-dione

(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

(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

Downstream raw materials:

(+/-)-tirandamycin B

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