Microsclerodermin E

Base Information

• Chemical Name: Microsclerodermin E
• CAS No.: 206535-31-1
• Molecular Formula: C45H54N8O14
• Molecular Weight: 930.95500

Synonyms:

Chemical Property of Microsclerodermin E

Chemical Property:

• PSA: 338.15000
• LogP: -0.22600

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Microsclerodermin E

There total 35 articles about Microsclerodermin E 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:

1,2-anhydro-3,4:5,6-di-O-isopropylidene-D-glucitol (85325-93-5,105454-09-9,105454-10-2) → microsclerodermin E (206535-31-1)

Guidance literature:

Multi-step reaction with 24 steps

1.1: 84 percent / BF₃*OEt₂ / tetrahydrofuran / -78 °C

2.1: hydrochloric acid / tetrahydrofuran

2.2: 67 percent / TsOH / acetone

3.1: 97 percent / 4-(dimethylamino)pyridine; triethylamine

4.1: 83 percent / NaN₃ / dimethylformamide / 120 °C

5.1: H₂ / Pd/C

6.1: pyridine

7.1: n-butyllithium / tetrahydrofuran / -78 °C

7.2: tetrahydrofuran

8.1: 4-(dimethylamino)pyridine; triethylamine

9.1: Na(Hg) / methanol

10.1: 87 percent / pyridinium p-toluenesulfonate / methanol / 45 °C

11.1: 92 percent / imidazole

12.1: 100 percent / diisopropylethylamine

13.1: 100 percent / Bu₄NF / tetrahydrofuran

14.1: 100 percent / NaBH₄ / ethanol

15.1: 96 percent / ethyl acetate / Heating

16.1: Dess-Martin periodinane

17.1: NaClO₂; resorcinol; NaH₂PO₄

18.1: 85 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

19.1: 80 percent / NaHCO₃ / acetonitrile

20.1: Bu₄NF / tetrahydrofuran

21.1: trimethylphosphine / tetrahydrofuran

22.1: diphenylphosphoryl azide / dimethylformamide / 336 h

23.1: LiOH / methanol; tetrahydrofuran

24.1: Amberlyst-15 / methanol; H₂O

With pyridine; 1H-imidazole; hydrogenchloride; dmap; lithium hydroxide; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; n-butyllithium; sodium azide; sodium amalgam; amberlyst-15; boron trifluoride diethyl etherate; diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; Dess-Martin periodane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; recorcinol; trimethylphosphane; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 16.1: Dess-Martin oxidation;

DOI:10.1002/anie.200352423

Reference yield:

3,4;5,6-di-O-isopropylidene-D-gluconic acid (52326-97-3) → microsclerodermin E (206535-31-1)

Guidance literature:

Multi-step reaction with 27 steps

1.1: 100 percent / NaBH₄ / methanol

2.1: 85 percent / pyridine

3.1: 89 percent / K₂CO₃ / methanol

4.1: 84 percent / BF₃*OEt₂ / tetrahydrofuran / -78 °C

5.1: hydrochloric acid / tetrahydrofuran

5.2: 67 percent / TsOH / acetone

6.1: 97 percent / 4-(dimethylamino)pyridine; triethylamine

7.1: 83 percent / NaN₃ / dimethylformamide / 120 °C

8.1: H₂ / Pd/C

9.1: pyridine

10.1: n-butyllithium / tetrahydrofuran / -78 °C

10.2: tetrahydrofuran

11.1: 4-(dimethylamino)pyridine; triethylamine

12.1: Na(Hg) / methanol

13.1: 87 percent / pyridinium p-toluenesulfonate / methanol / 45 °C

14.1: 92 percent / imidazole

15.1: 100 percent / diisopropylethylamine

16.1: 100 percent / Bu₄NF / tetrahydrofuran

17.1: 100 percent / NaBH₄ / ethanol

18.1: 96 percent / ethyl acetate / Heating

19.1: Dess-Martin periodinane

20.1: NaClO₂; resorcinol; NaH₂PO₄

21.1: 85 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

22.1: 80 percent / NaHCO₃ / acetonitrile

23.1: Bu₄NF / tetrahydrofuran

24.1: trimethylphosphine / tetrahydrofuran

25.1: diphenylphosphoryl azide / dimethylformamide / 336 h

26.1: LiOH / methanol; tetrahydrofuran

27.1: Amberlyst-15 / methanol; H₂O

With pyridine; 1H-imidazole; hydrogenchloride; dmap; lithium hydroxide; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; n-butyllithium; sodium azide; sodium amalgam; amberlyst-15; boron trifluoride diethyl etherate; diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; recorcinol; trimethylphosphane; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 19.1: Dess-Martin oxidation;

DOI:10.1002/anie.200352423

Reference yield:

3,4:5,6-di-O-isopropylidene-1-O-p-tolylsulfonyl-D-glucitol (104527-46-0) → microsclerodermin E (206535-31-1)

Guidance literature:

Multi-step reaction with 25 steps

1.1: 89 percent / K₂CO₃ / methanol

2.1: 84 percent / BF₃*OEt₂ / tetrahydrofuran / -78 °C

3.1: hydrochloric acid / tetrahydrofuran

3.2: 67 percent / TsOH / acetone

4.1: 97 percent / 4-(dimethylamino)pyridine; triethylamine

5.1: 83 percent / NaN₃ / dimethylformamide / 120 °C

6.1: H₂ / Pd/C

7.1: pyridine

8.1: n-butyllithium / tetrahydrofuran / -78 °C

8.2: tetrahydrofuran

9.1: 4-(dimethylamino)pyridine; triethylamine

10.1: Na(Hg) / methanol

11.1: 87 percent / pyridinium p-toluenesulfonate / methanol / 45 °C

12.1: 92 percent / imidazole

13.1: 100 percent / diisopropylethylamine

14.1: 100 percent / Bu₄NF / tetrahydrofuran

15.1: 100 percent / NaBH₄ / ethanol

16.1: 96 percent / ethyl acetate / Heating

17.1: Dess-Martin periodinane

18.1: NaClO₂; resorcinol; NaH₂PO₄

19.1: 85 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

20.1: 80 percent / NaHCO₃ / acetonitrile

21.1: Bu₄NF / tetrahydrofuran

22.1: trimethylphosphine / tetrahydrofuran

23.1: diphenylphosphoryl azide / dimethylformamide / 336 h

24.1: LiOH / methanol; tetrahydrofuran

25.1: Amberlyst-15 / methanol; H₂O

With pyridine; 1H-imidazole; hydrogenchloride; dmap; lithium hydroxide; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; n-butyllithium; sodium azide; sodium amalgam; amberlyst-15; boron trifluoride diethyl etherate; diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; recorcinol; trimethylphosphane; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 17.1: Dess-Martin oxidation;

DOI:10.1002/anie.200352423

upstream raw materials:

1,2-anhydro-3,4:5,6-di-O-isopropylidene-D-glucitol

3,4;5,6-di-O-isopropylidene-D-gluconic acid

3,4:5,6-di-O-isopropylidene-1-O-p-tolylsulfonyl-D-glucitol

D-Glucono-1,5-lactone

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