(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

Base Information

• Chemical Name: (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
• CAS No.: 378741-96-9
• Molecular Formula: C₂₉H₃₆O₈
• Molecular Weight: 512.6

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of (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

There total 11 articles about (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 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: 91.0%

(E)-(S)-5-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-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 (378741-95-8) → (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 (378741-96-9)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 40 ℃; for 36h;

DOI:10.1021/ol0166597

Reference yield:

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 (131311-03-0) → (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 (378741-96-9)

Guidance literature:

Multi-step reaction with 10 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

With titanium(IV) isopropylate; osmium(VIII) oxide; pyridine-SO₃ complex; 4 Angstroem molecular sievws; potassium tert-butylate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; 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:

(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 (374638-43-4) → (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 (378741-96-9)

Guidance literature:

Multi-step reaction with 9 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

With titanium(IV) isopropylate; pyridine-SO₃ complex; 4 Angstroem molecular sievws; potassium tert-butylate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; 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

upstream raw materials:

(E)-(S)-5-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-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

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

(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

(E)-3-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-4a,6-dimethyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-prop-2-en-1-ol

Downstream raw materials:

(2R,4aR,5S,7S,8aR,9aS,10aS)-7-Allyl-5-(4-methoxy-benzyloxy)-4a,10a-dimethyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracene

(2R,4aR,5S,7S,8aR,9aS,10aS)-5-Benzyloxy-7-(3-benzyloxy-propyl)-4a,10a-dimethyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracene

(2R,3S,4aR,5S,7S,8aR,9aS,10aS)-5-Benzyloxy-7-(3-benzyloxy-propyl)-4a,10a-dimethyl-2-vinyl-decahydro-1,8,10-trioxa-anthracen-3-ol

(2S,3S,4aR,6S,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,8a-dimethyl-octahydro-pyrano[3,2-b]pyran-2-carbaldehyde

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