(+/-)-sarubicin A (U-58,431)

Base Information

• Chemical Name: (+/-)-sarubicin A (U-58,431)
• CAS No.: 87392-60-7
• Molecular Formula: C₁₃H₁₄N₂O₆
• Molecular Weight: 294.264
• Mol file: 87392-60-7.mol

Synonyms:

Chemical Property of (+/-)-sarubicin A (U-58,431)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-sarubicin A (U-58,431)

There total 14 articles about (+/-)-sarubicin A (U-58,431) 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-(2,5-dimethoxybenzoyl)propionic acid (1084-74-8) → (+/-)-sarubicin A (U-58,431) (87392-60-7,74639-67-1)

Guidance literature:

Multi-step reaction with 12 steps

1: 70 percent / AlCl₃ / acetonitrile / 65 °C

2: 81 percent / Br₂, NaOAc / acetic acid / Ambient temperature

3: 1.) Ac₂O, 5percent NaOH, 2.) NaBH₄ / 1.) ice, 3 min, 2.) aq. THF, 15 deg C, 1 h

4: 83 percent / aq. KOH / Ambient temperature

5: 64 percent / 95percent H₂SO₄ / 0.5 h / 70 - 80 °C

7: 96 percent / OsO₄, Me₃N(O) / OsO₄ / 2-methyl-propan-2-ol / 1.5 h / 70 °C

9: 96 percent / AgClO₄ / tetrahydrofuran / 0.33 h / Ambient temperature

10: 90 percent / alkaline hydrogen peroxide

11: 70 percent / MeSLi / dimethylformamide / 2 h / 155 °C

12: 1.) CAN, 2.) NH₃ / 1.) MeCN, room temp., 2.) MeCN

With potassium hydroxide; sodium hydroxide; sodium tetrahydroborate; osmium(VIII) oxide; aluminium trichloride; ammonium cerium(IV) nitrate; trimethylamine-N-oxide; alkaline hydrogen peroxide; sulfuric acid; ammonia; bromine; sodium acetate; silver perchlorate; acetic anhydride; lithium methanethiolate; osmium(VIII) oxide; In tetrahydrofuran; acetic acid; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;

DOI:10.1021/jo00170a068

Reference yield:

4-(2-Hydroxy-5-methoxyphenyl)-4-oxobutanoic Acid (75501-54-1) → (+/-)-sarubicin A (U-58,431) (87392-60-7,74639-67-1)

Guidance literature:

Multi-step reaction with 11 steps

1: 81 percent / Br₂, NaOAc / acetic acid / Ambient temperature

2: 1.) Ac₂O, 5percent NaOH, 2.) NaBH₄ / 1.) ice, 3 min, 2.) aq. THF, 15 deg C, 1 h

3: 83 percent / aq. KOH / Ambient temperature

4: 64 percent / 95percent H₂SO₄ / 0.5 h / 70 - 80 °C

6: 96 percent / OsO₄, Me₃N(O) / OsO₄ / 2-methyl-propan-2-ol / 1.5 h / 70 °C

8: 96 percent / AgClO₄ / tetrahydrofuran / 0.33 h / Ambient temperature

9: 90 percent / alkaline hydrogen peroxide

10: 70 percent / MeSLi / dimethylformamide / 2 h / 155 °C

11: 1.) CAN, 2.) NH₃ / 1.) MeCN, room temp., 2.) MeCN

With potassium hydroxide; sodium hydroxide; sodium tetrahydroborate; osmium(VIII) oxide; ammonium cerium(IV) nitrate; trimethylamine-N-oxide; alkaline hydrogen peroxide; sulfuric acid; ammonia; bromine; sodium acetate; silver perchlorate; acetic anhydride; lithium methanethiolate; osmium(VIII) oxide; In tetrahydrofuran; acetic acid; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1021/jo00170a068

Reference yield:

4-(3-Bromo-2-hydroxy-5-methoxy-phenyl)-butyric acid (87338-26-9) → (+/-)-sarubicin A (U-58,431) (87392-60-7,74639-67-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 83 percent / aq. KOH / Ambient temperature

2: 64 percent / 95percent H₂SO₄ / 0.5 h / 70 - 80 °C

4: 96 percent / OsO₄, Me₃N(O) / OsO₄ / 2-methyl-propan-2-ol / 1.5 h / 70 °C

6: 96 percent / AgClO₄ / tetrahydrofuran / 0.33 h / Ambient temperature

7: 90 percent / alkaline hydrogen peroxide

8: 70 percent / MeSLi / dimethylformamide / 2 h / 155 °C

9: 1.) CAN, 2.) NH₃ / 1.) MeCN, room temp., 2.) MeCN

With potassium hydroxide; osmium(VIII) oxide; ammonium cerium(IV) nitrate; trimethylamine-N-oxide; alkaline hydrogen peroxide; sulfuric acid; ammonia; silver perchlorate; lithium methanethiolate; osmium(VIII) oxide; In tetrahydrofuran; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1021/jo00170a068

upstream raw materials:

(1S,8R,10R,11R)-1,6,11-Trihydroxy-3-methoxy-10-methyl-9-oxa-tricyclo[6.2.2.0^2,7]dodeca-2⁽⁷⁾,3,5-triene-5-carboxylic acid amide

3-(2,5-dimethoxybenzoyl)propionic acid

4-(2-Hydroxy-5-methoxyphenyl)-4-oxobutanoic Acid

4-(3-Bromo-2-hydroxy-5-methoxy-phenyl)-butyric acid