6H-Benzofuro[3,2-c][1]benzopyran-3-ol,6a,11a-dihydro-4-[(5-hydroxy-6-methoxy-3-phenyl-2-benzofuranyl)methyl]-9-methoxy-,(6aS,11aS)-

Base Information

Chemical Name:6H-Benzofuro[3,2-c][1]benzopyran-3-ol,6a,11a-dihydro-4-[(5-hydroxy-6-methoxy-3-phenyl-2-benzofuranyl)methyl]-9-methoxy-,(6aS,11aS)-
CAS No.:164124-45-2
Molecular Formula:C32H26 O7
Molecular Weight:522.554
Hs Code.:
Mol file:164124-45-2.mol

Synonyms:6H-Benzofuro[3,2-c][1]benzopyran-3-ol,6a,11a-dihydro-4-[(5-hydroxy-6-methoxy-3-phenyl-2-benzofuranyl)methyl]-9-methoxy-,(6aS-cis)-; Daljanelin B

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Chemical Property of 6H-Benzofuro[3,2-c][1]benzopyran-3-ol,6a,11a-dihydro-4-[(5-hydroxy-6-methoxy-3-phenyl-2-benzofuranyl)methyl]-9-methoxy-,(6aS,11aS)-

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MSDS Files:: SDS file from LookChem

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Technology Process of 6H-Benzofuro[3,2-c][1]benzopyran-3-ol,6a,11a-dihydro-4-[(5-hydroxy-6-methoxy-3-phenyl-2-benzofuranyl)methyl]-9-methoxy-,(6aS,11aS)-

There total 13 articles about 6H-Benzofuro[3,2-c][1]benzopyran-3-ol,6a,11a-dihydro-4-[(5-hydroxy-6-methoxy-3-phenyl-2-benzofuranyl)methyl]-9-methoxy-,(6aS,11aS)- 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:

: 33983-39-0
medicarpin

: 164124-45-2
(6aS,11aS)-4-(5-Hydroxy-6-methoxy-3-phenyl-1-benzofuran-2-ylmethyl)medicarpin

Guidance literature:: Multi-step reaction with 13 steps

1.1: 80 percent / K₂CO₃ / acetone / Heating

2.1: 55 percent / various solvent(s) / Heating

3.1: pyridine / 12 h / 30 °C

4.1: 99 percent / PdCl₂(PhCN)2 / benzene / Heating

5.1: 74 percent / KOH; MeOH / Heating

6.1: NaH / tetrahydrofuran / 0.17 h

6.2: 61 percent / tetrahydrofuran

7.1: 61 percent / NMO; H₂O; OsO₄ / 2-methyl-propan-2-ol / 20 °C

8.1: 73 percent / NaIO₄; H₂O / methanol / 20 °C

9.1: 85 percent / NaBH₄ / ethanol; tetrahydrofuran / 20 °C

10.1: 100 percent / 2,6-lutidine; Ms₂O; LiBr / tetrahydrofuran / 20 °C

11.1: 28 percent / tris(dimethylamino)sulfonium difluorotrimethylsilicate; HMPA / tetrahydrofuran / 15 h / -78 - -30 °C

12.1: 22 percent / tetrahydrofuran / 20 °C

13.1: 24 percent / HCl; H₂O / methanol / 3 h / Heating

With pyridine; 2,6-dimethylpyridine; hydrogenchloride; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; tris(dimethylamino)sulfonium trimethylsilyldifluoride; water; sodium hydride; potassium carbonate; lithium bromide; Methanesulfonic anhydride; bis(benzonitrile)palladium(II) dichloride; In tetrahydrofuran; methanol; ethanol; acetone; tert-butyl alcohol; benzene; 1.1: Alkylation / 2.1: Rearrangement / 3.1: Esterification / 4.1: Isomerization / 5.1: Saponification / 6.1: Metallation / 6.2: Etherification / 7.1: Oxidation / 8.1: Oxidation / 9.1: Reduction / 10.1: Substitution / 11.1: Alkylation / 12.1: Grignard reaction / 13.1: Dehydration;
DOI:10.1039/a904944d

Reference yield:

: 258854-20-5
(6aS,11aS)-3-O-Allylmedicarpin

: 164124-45-2
(6aS,11aS)-4-(5-Hydroxy-6-methoxy-3-phenyl-1-benzofuran-2-ylmethyl)medicarpin

Guidance literature:: Multi-step reaction with 13 steps

1.1: 55 percent / various solvent(s) / Heating

2.1: pyridine / 12 h / 30 °C

3.1: 99 percent / PdCl₂(PhCN)2 / benzene / Heating

4.1: 74 percent / KOH; MeOH / Heating

5.1: NaH / tetrahydrofuran / 0.17 h

5.2: 61 percent / tetrahydrofuran

6.1: 61 percent / NMO; H₂O; OsO₄ / 2-methyl-propan-2-ol / 20 °C

7.1: 73 percent / NaIO₄; H₂O / methanol / 20 °C

8.1: 85 percent / NaBH₄ / ethanol; tetrahydrofuran / 20 °C

9.1: 100 percent / 2,6-lutidine; Ms₂O; LiBr / tetrahydrofuran / 20 °C

10.1: 28 percent / tris(dimethylamino)sulfonium difluorotrimethylsilicate; HMPA / tetrahydrofuran / 15 h / -78 - -30 °C

11.1: 22 percent / tetrahydrofuran / 20 °C

12.1: 24 percent / HCl; H₂O / methanol / 3 h / Heating

13.1: 70 percent / TFA; Na(CN)BH₃ / CH₂Cl₂ / 1 h / -10 - 0 °C

With pyridine; 2,6-dimethylpyridine; hydrogenchloride; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; tris(dimethylamino)sulfonium trimethylsilyldifluoride; water; sodium hydride; sodium cyanoborohydride; trifluoroacetic acid; lithium bromide; Methanesulfonic anhydride; bis(benzonitrile)palladium(II) dichloride; In tetrahydrofuran; methanol; ethanol; dichloromethane; tert-butyl alcohol; benzene; 1.1: Rearrangement / 2.1: Esterification / 3.1: Isomerization / 4.1: Saponification / 5.1: Metallation / 5.2: Etherification / 6.1: Oxidation / 7.1: Oxidation / 8.1: Reduction / 9.1: Substitution / 10.1: Alkylation / 11.1: Grignard reaction / 12.1: Dehydration / 13.1: Ring cleavage;
DOI:10.1039/a904944d

Reference yield:

: 258854-21-6
(6aS,11aS)-4-Allylmedicarpin

: 164124-45-2
(6aS,11aS)-4-(5-Hydroxy-6-methoxy-3-phenyl-1-benzofuran-2-ylmethyl)medicarpin

Guidance literature:: Multi-step reaction with 11 steps

1.1: pyridine / 12 h / 30 °C

2.1: 99 percent / PdCl₂(PhCN)2 / benzene / Heating

3.1: 74 percent / KOH; MeOH / Heating

4.1: NaH / tetrahydrofuran / 0.17 h

4.2: 61 percent / tetrahydrofuran

5.1: 61 percent / NMO; H₂O; OsO₄ / 2-methyl-propan-2-ol / 20 °C

6.1: 73 percent / NaIO₄; H₂O / methanol / 20 °C

7.1: 85 percent / NaBH₄ / ethanol; tetrahydrofuran / 20 °C

8.1: 100 percent / 2,6-lutidine; Ms₂O; LiBr / tetrahydrofuran / 20 °C

9.1: 28 percent / tris(dimethylamino)sulfonium difluorotrimethylsilicate; HMPA / tetrahydrofuran / 15 h / -78 - -30 °C

10.1: 22 percent / tetrahydrofuran / 20 °C

11.1: 24 percent / HCl; H₂O / methanol / 3 h / Heating

With pyridine; 2,6-dimethylpyridine; hydrogenchloride; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; tris(dimethylamino)sulfonium trimethylsilyldifluoride; water; sodium hydride; lithium bromide; Methanesulfonic anhydride; bis(benzonitrile)palladium(II) dichloride; In tetrahydrofuran; methanol; ethanol; tert-butyl alcohol; benzene; 1.1: Esterification / 2.1: Isomerization / 3.1: Saponification / 4.1: Metallation / 4.2: Etherification / 5.1: Oxidation / 6.1: Oxidation / 7.1: Reduction / 8.1: Substitution / 9.1: Alkylation / 10.1: Grignard reaction / 11.1: Dehydration;
DOI:10.1039/a904944d