[(2R,4aR,5S,7R,8aR,9aS,10aS)-5-(4-Methoxy-benzyloxy)-4a,10a-dimethyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-7-yl]-acetic acid methyl ester

Base Information

Chemical Name:[(2R,4aR,5S,7R,8aR,9aS,10aS)-5-(4-Methoxy-benzyloxy)-4a,10a-dimethyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-7-yl]-acetic acid methyl ester
CAS No.:378741-97-0
Molecular Formula:C₂₉H₃₆O₈
Molecular Weight:512.6
Hs Code.:

Synonyms:[(2R,4aR,5S,7R,8aR,9aS,10aS)-5-(4-Methoxy-benzyloxy)-4a,10a-dimethyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-7-yl]-acetic acid methyl ester

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Chemical Property of [(2R,4aR,5S,7R,8aR,9aS,10aS)-5-(4-Methoxy-benzyloxy)-4a,10a-dimethyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-7-yl]-acetic acid methyl ester

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Technology Process of [(2R,4aR,5S,7R,8aR,9aS,10aS)-5-(4-Methoxy-benzyloxy)-4a,10a-dimethyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-7-yl]-acetic acid methyl ester

There total 12 articles about [(2R,4aR,5S,7R,8aR,9aS,10aS)-5-(4-Methoxy-benzyloxy)-4a,10a-dimethyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-7-yl]-acetic acid methyl ester 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: 86.0%

: 378741-96-9
(E)-(S)-5-((2R,4aR,6R,7R,8aS)-7-Hydroxy-4a,6-dimethyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-5-(4-methoxy-benzyloxy)-pent-2-enoic acid methyl ester

: 378741-97-0
[(2R,4aR,5S,7R,8aR,9aS,10aS)-5-(4-Methoxy-benzyloxy)-4a,10a-dimethyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-7-yl]-acetic acid methyl ester

Guidance literature:: With sodium hydride; In tetrahydrofuran; at 20 ℃; for 1h;
DOI:10.1021/ol0166597

Reference yield:

: 131311-03-0
tert-Butyl-((2R,4aR,6S,7R,8aS)-4a,6-dimethyl-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-dimethyl-silane

: 378741-97-0
[(2R,4aR,5S,7R,8aR,9aS,10aS)-5-(4-Methoxy-benzyloxy)-4a,10a-dimethyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-7-yl]-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 11 steps

1.1: OsO₄; N-methylmorpholine N-oxide / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 20 °C

1.2: NaIO₄ / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 1 h / 20 °C

2.1: potassium t-butoxide / tetrahydrofuran / 1 h / 0 - 20 °C

2.2: 6.01 g / tetrahydrofuran / 2 h / -78 - 0 °C

3.1: 5.49 g / DIBALH / CH₂Cl₂; hexane / 1 h / -78 °C

4.1: (-)-diethyl tartrate; Ti(Oi-Pr)4; 4 Angstroem molecular sievws / CH₂Cl₂ / 0.5 h / -28 °C

4.2: 1.81 g / t-BuOOH / CH₂Cl₂; 2,2,4-trimethyl-pentane / 20 h / -28 °C

5.1: 100 percent / Red-Al / tetrahydrofuran; toluene / 1.5 h / 0 °C

6.1: piridinium p-toluenesulfonate / CH₂Cl₂ / 0.67 h / 20 °C

7.1: 4.50 g / DIBALH / CH₂Cl₂; hexane / 0.75 h / 0 °C

8.1: SO₃*pyridine; Et₃N / dimethylsulfoxide; CH₂Cl₂ / 0.75 h / 0 °C

9.1: 0.92 g / toluene / 2.67 h / 80 °C

10.1: 91 percent / tetra-n-butylammonium fluoride; AcOH / tetrahydrofuran / 20 - 40 °C

11.1: 86 percent / NaH / tetrahydrofuran / 1 h / 20 °C

With titanium(IV) isopropylate; osmium(VIII) oxide; pyridine-SO₃ complex; 4 Angstroem molecular sievws; potassium tert-butylate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; acetic acid; 4-methylmorpholine N-oxide; (-)-diethyl tartrate; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; hexane; dichloromethane; water; dimethyl sulfoxide; toluene; tert-butyl alcohol; 2.1: Horner-Wadsworth-Emmons reaction / 4.1: Sharpless asymmetric epoxidation;
DOI:10.1021/ja028167a

Reference yield:

: 374638-43-4
(2R,4aR,6R,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-4a,6-dimethyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-6-carbaldehyde

: 378741-97-0
[(2R,4aR,5S,7R,8aR,9aS,10aS)-5-(4-Methoxy-benzyloxy)-4a,10a-dimethyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-7-yl]-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 10 steps

1.1: potassium t-butoxide / tetrahydrofuran / 1 h / 0 - 20 °C

1.2: 6.01 g / tetrahydrofuran / 2 h / -78 - 0 °C

2.1: 5.49 g / DIBALH / CH₂Cl₂; hexane / 1 h / -78 °C

3.1: (-)-diethyl tartrate; Ti(Oi-Pr)4; 4 Angstroem molecular sievws / CH₂Cl₂ / 0.5 h / -28 °C

3.2: 1.81 g / t-BuOOH / CH₂Cl₂; 2,2,4-trimethyl-pentane / 20 h / -28 °C

4.1: 100 percent / Red-Al / tetrahydrofuran; toluene / 1.5 h / 0 °C

5.1: piridinium p-toluenesulfonate / CH₂Cl₂ / 0.67 h / 20 °C

6.1: 4.50 g / DIBALH / CH₂Cl₂; hexane / 0.75 h / 0 °C

7.1: SO₃*pyridine; Et₃N / dimethylsulfoxide; CH₂Cl₂ / 0.75 h / 0 °C

8.1: 0.92 g / toluene / 2.67 h / 80 °C

9.1: 91 percent / tetra-n-butylammonium fluoride; AcOH / tetrahydrofuran / 20 - 40 °C

10.1: 86 percent / NaH / tetrahydrofuran / 1 h / 20 °C

With titanium(IV) isopropylate; pyridine-SO₃ complex; 4 Angstroem molecular sievws; potassium tert-butylate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; acetic acid; (-)-diethyl tartrate; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; toluene; 1.1: Horner-Wadsworth-Emmons reaction / 3.1: Sharpless asymmetric epoxidation;
DOI:10.1021/ja028167a