17-epi-7-O-Benzoyltheopederin D

Base Information

• Chemical Name: 17-epi-7-O-Benzoyltheopederin D
• CAS No.: 302355-98-2
• Molecular Formula: C₃₃H₄₅NO₁₁
• Molecular Weight: 631.72
• Mol file: 302355-98-2.mol

Synonyms:

Chemical Property of 17-epi-7-O-Benzoyltheopederin D

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 17-epi-7-O-Benzoyltheopederin D

There total 23 articles about 17-epi-7-O-Benzoyltheopederin D 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:

Benzoic acid (S)-[(4S,4aS,6R,8S,8aR)-6-(2,5-dihydroxy-pentyl)-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl]-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-methyl ester (218965-73-2) → 17-epi-7-O-Benzoyltheopederin D (302355-98-2) + 7-O-Benzoyltheopederin D (218965-74-3)

Guidance literature:

With N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; In dichloromethane; acetonitrile; for 0.5h; Yields of byproduct given; Ambient temperature;

DOI:10.1055/s-1998-1970

Reference yield:

(4R,5R,6R)-5,6-Dimethyl-4-(phenylselanylmethyl)tetrahydro-2H-pyran-2-one (139403-50-2) → 17-epi-7-O-Benzoyltheopederin D (302355-98-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 80 mg

2.1: LiBH(s-Bu)3 / tetrahydrofuran / 0.25 h / -95 °C

3.1: CSA / CH₂Cl₂ / 0.67 h / 20 °C

4.1: DMAP; DIPEA; 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / 20 °C

5.1: hydroquinine 9-phenanthryl ether; potassium osmate dihydrate; aq. K₃Fe(CN)6 / 2-methyl-propan-2-ol / 8 h / 20 °C

6.1: aq. NaIO₄ / methanol / 1 h / 20 °C

7.1: 27 mg / Et₃N / toluene / 0.03 h / Heating

8.1: MeMgCl; Mg; 1,2-dibromoethane / tetrahydrofuran / 3 h / Heating

8.2: 20 mg / tetrahydrofuran / 2 h / -78 °C

9.1: 4 mg / 4-methylmorpholine N-oxide; TPAP; 4 Angstroem molecular sieves / CH₂Cl₂; acetonitrile / 0.5 h / 20 °C

With dmap; potassium osmate(VI); sodium periodate; tetrapropylammonium perruthennate; 4 A molecular sieve; camphor-10-sulfonic acid; methylmagnesium chloride; L-Selectride; magnesium; 4-methylmorpholine N-oxide; dihydroquinine 9-O-(9'-phenanthryl) ether; ethylene dibromide; triethylamine; N-ethyl-N,N-diisopropylamine; potassium hexacyanoferrate(III); In tetrahydrofuran; methanol; dichloromethane; toluene; acetonitrile; tert-butyl alcohol; 2.1: Reduction / 3.1: Addition / 4.1: Acylation / 5.1: Oxidation / 6.1: Oxidation / 7.1: Elimination / 8.1: Metallation / 8.2: Grignard reaction / 9.1: Oxidation;

DOI:10.1039/a909898d

Reference yield:

(+)-(1R,5R,6R,8R,10S)-5-(hydroxy)methyl-10-methoxy-9,9-dimethyl-8-(prop-2-enyl)-2,4,7-trioxabicyclo[4.4.0]decane (207276-55-9) → 17-epi-7-O-Benzoyltheopederin D (302355-98-2)

Guidance literature:

Multi-step reaction with 13 steps

1.1: PDC / dimethylformamide / 23 h / 20 °C

2.1: 171 mg / (PhO)2PON₃; DIPEA; 4 Angstroem molecular sieves / toluene / 1 h / 65 °C

3.1: 66 percent / DMAP / CH₂Cl₂ / 91 h / 20 °C

4.1: 83 percent / TBAF*3H₂O / tetrahydrofuran / 0.03 h / 0 °C

5.1: 80 mg

6.1: LiBH(s-Bu)3 / tetrahydrofuran / 0.25 h / -95 °C

7.1: CSA / CH₂Cl₂ / 0.67 h / 20 °C

8.1: DMAP; DIPEA; 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / 20 °C

9.1: hydroquinine 9-phenanthryl ether; potassium osmate dihydrate; aq. K₃Fe(CN)6 / 2-methyl-propan-2-ol / 8 h / 20 °C

10.1: aq. NaIO₄ / methanol / 1 h / 20 °C

11.1: 27 mg / Et₃N / toluene / 0.03 h / Heating

12.1: MeMgCl; Mg; 1,2-dibromoethane / tetrahydrofuran / 3 h / Heating

12.2: 20 mg / tetrahydrofuran / 2 h / -78 °C

13.1: 4 mg / 4-methylmorpholine N-oxide; TPAP; 4 Angstroem molecular sieves / CH₂Cl₂; acetonitrile / 0.5 h / 20 °C

With dmap; potassium osmate(VI); sodium periodate; dipyridinium dichromate; tetrapropylammonium perruthennate; 4 A molecular sieve; diphenyl phosphoryl azide; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; methylmagnesium chloride; L-Selectride; magnesium; 4-methylmorpholine N-oxide; dihydroquinine 9-O-(9'-phenanthryl) ether; ethylene dibromide; triethylamine; N-ethyl-N,N-diisopropylamine; potassium hexacyanoferrate(III); In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; 1.1: Oxidation / 2.1: Rearrangement / 3.1: Acylation / 4.1: Hydrolysis / 6.1: Reduction / 7.1: Addition / 8.1: Acylation / 9.1: Oxidation / 10.1: Oxidation / 11.1: Elimination / 12.1: Metallation / 12.2: Grignard reaction / 13.1: Oxidation;

DOI:10.1039/a909898d

upstream raw materials:

Benzoic acid (S)-[(4S,4aS,6R,8S,8aR)-6-(2,5-dihydroxy-pentyl)-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl]-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-methyl ester

(4R,5R,6R)-5,6-Dimethyl-4-(phenylselanylmethyl)tetrahydro-2H-pyran-2-one

(+)-(1R,5R,6R,8R,10S)-5-(hydroxy)methyl-10-methoxy-9,9-dimethyl-8-(prop-2-enyl)-2,4,7-trioxabicyclo[4.4.0]decane

(R)-4-[(1R,2R)-2-(4-Chlorobenzoyloxy)-1-methylpropyl]dihydrofuran-2(2H)-one