C₂₈H₂₂O₁₁

Base Information

• Chemical Name: C₂₈H₂₂O₁₁
• CAS No.: 183733-34-8
• Molecular Formula: C₂₈H₂₂O₁₁
• Molecular Weight: 534.476
• Mol file: 183733-34-8.mol

Synonyms:

Chemical Property of C₂₈H₂₂O₁₁

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of C₂₈H₂₂O₁₁

There total 26 articles about C₂₈H₂₂O₁₁ 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: 89.0%

1,1'-carbonyldiimidazole (530-62-1) + C27H24O10 (183733-33-7) → C28H22O11 (183733-34-8)

Guidance literature:

1,1'-carbonyldiimidazole; C₂₇H₂₄O₁₀; In tetrahydrofuran; at 0 - 23 ℃;

With camphor-10-sulfonic acid; In water; acetonitrile; at 23 ℃; for 0.5h; Further stages.;

DOI:10.1021/ja012487x

Reference yield:

(R)-1-{(2R,3R)-3-[(tert-Butyl-dimethyl-silanyl)-ethynyl]-2-ethynyl-oxiranyl}-ethane-1,2-diol (183733-37-1) → C28H22O11 (183733-34-8)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 91 percent / p-toluenesulfonic acid / dimethylformamide / 6 h / 23 °C

2.1: lithium hexamethyldisilazide / toluene / 0.42 h / -78 °C

2.2: 5.55 g / toluene / 0.67 h / -78 °C

3.1: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C

4.1: 92 percent / 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 - 23 °C

5.1: 90 percent / p-toluenesulfonic acid / acetone / 0.25 h / 23 °C

6.1: 88 percent / 2,6-lutidine / CH₂Cl₂ / 0.33 h / -78 °C

7.1: 94 percent / diisobutylaluminum hydride / toluene; CH₂Cl₂ / 0.17 h / -78 °C

8.1: (+)-diethyl-L-tartrate; titanium(IV) isopropoxide / CH₂Cl₂ / 0.5 h

8.2: 98 percent / tert-butyl hydroperoxide / CH₂Cl₂ / 15 h

9.1: 97 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 0.67 h / 23 °C

10.1: 85 percent / 1,3-diphenyl-1,1,3,3-tetramethyldisilazine; n-butyllithium / tetrahydrofuran / 0.17 h / -78 °C

11.1: 89 percent / pyridine / CH₂Cl₂ / 0.17 h / 0 °C

12.1: 100 percent / Et₃N*3HF / tetrahydrofuran / 2.5 h / 23 °C

13.1: tetrahydrofuran / 0.25 h / -10 °C

13.2: DCC / 0.17 h / -10 °C

13.3: n-propylamine / 0.17 h / -10 °C

14.1: 81 percent / p-toluenesulfonic acid / methanol / 1.5 h / 23 °C

15.1: tetrahydrofuran / 0 - 23 °C

15.2: 89 percent / (+/-)-camphorsulfonic acid / acetonitrile; H₂O / 0.5 h / 23 °C

With pyridine; 2,6-dimethylpyridine; titanium(IV) isopropylate; dmap; n-butyllithium; diethyl L-tartrate; 1,1,3,3-tetramethyl-1,3-diphenyldisilazane; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine tris(hydrogen fluoride); triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1021/ja012487x

Reference yield:

t-butyl-[3-(2,2-dimethyl[1,3]dioxolan-4-yl)-3-ethynyloxiranylethynyl]dimethylsilane (439856-68-5) → C28H22O11 (183733-34-8)

Guidance literature:

Multi-step reaction with 14 steps

1.1: lithium hexamethyldisilazide / toluene / 0.42 h / -78 °C

1.2: 5.55 g / toluene / 0.67 h / -78 °C

2.1: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C

3.1: 92 percent / 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 - 23 °C

4.1: 90 percent / p-toluenesulfonic acid / acetone / 0.25 h / 23 °C

5.1: 88 percent / 2,6-lutidine / CH₂Cl₂ / 0.33 h / -78 °C

6.1: 94 percent / diisobutylaluminum hydride / toluene; CH₂Cl₂ / 0.17 h / -78 °C

7.1: (+)-diethyl-L-tartrate; titanium(IV) isopropoxide / CH₂Cl₂ / 0.5 h

7.2: 98 percent / tert-butyl hydroperoxide / CH₂Cl₂ / 15 h

8.1: 97 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 0.67 h / 23 °C

9.1: 85 percent / 1,3-diphenyl-1,1,3,3-tetramethyldisilazine; n-butyllithium / tetrahydrofuran / 0.17 h / -78 °C

10.1: 89 percent / pyridine / CH₂Cl₂ / 0.17 h / 0 °C

11.1: 100 percent / Et₃N*3HF / tetrahydrofuran / 2.5 h / 23 °C

12.1: tetrahydrofuran / 0.25 h / -10 °C

12.2: DCC / 0.17 h / -10 °C

12.3: n-propylamine / 0.17 h / -10 °C

13.1: 81 percent / p-toluenesulfonic acid / methanol / 1.5 h / 23 °C

14.1: tetrahydrofuran / 0 - 23 °C

14.2: 89 percent / (+/-)-camphorsulfonic acid / acetonitrile; H₂O / 0.5 h / 23 °C

With pyridine; 2,6-dimethylpyridine; titanium(IV) isopropylate; dmap; n-butyllithium; diethyl L-tartrate; 1,1,3,3-tetramethyl-1,3-diphenyldisilazane; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine tris(hydrogen fluoride); triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; acetone; toluene;

DOI:10.1021/ja012487x

upstream raw materials:

1,1'-carbonyldiimidazole

C₂₇H₂₄O₁₀

2-hydroxy-7-methoxy-5-methylnaphthalene-1-carboxylic acid methyl ester

2-hydroxy-7-methoxy-5-methylnaphthalene-1-carboxylic acid

Downstream raw materials:

neocarzinostatin chromophore

C₂₈H₂₀O₁₀