(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

Base Information

• Chemical Name: (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
• CAS No.: 378741-98-1
• Molecular Formula: C₂₉H₃₆O₆
• Molecular Weight: 480.601

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Technology Process of (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

There total 14 articles about (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 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:

Methyltriphenylphosphonium bromide (1779-49-3) + [(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]-acetaldehyde → (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 (378741-98-1)

Guidance literature:

Methyltriphenylphosphonium bromide; With sodium hexamethyldisilazane; In tetrahydrofuran; at 0 ℃; for 0.333333h;

[(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]-acetaldehyde; In tetrahydrofuran; at 0 ℃; for 15h; Further stages.;

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) → (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 (378741-98-1)

Guidance literature:

Multi-step reaction with 13 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

12.1: DIBALH / CH₂Cl₂; hexane / 0.5 h / -78 °C

13.1: NaHMDS / tetrahydrofuran / 0.33 h / 0 °C

13.2: 1.07 g / tetrahydrofuran / 0.25 h / 0 °C

With titanium(IV) isopropylate; osmium(VIII) oxide; pyridine-SO₃ complex; 4 Angstroem molecular sievws; potassium tert-butylate; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; 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 / 13.1: Wittig methylenation;

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) → (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 (378741-98-1)

Guidance literature:

Multi-step reaction with 12 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

11.1: DIBALH / CH₂Cl₂; hexane / 0.5 h / -78 °C

12.1: NaHMDS / tetrahydrofuran / 0.33 h / 0 °C

12.2: 1.07 g / tetrahydrofuran / 0.25 h / 0 °C

With titanium(IV) isopropylate; pyridine-SO₃ complex; 4 Angstroem molecular sievws; potassium tert-butylate; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; 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 / 12.1: Wittig methylenation;

DOI:10.1021/ja028167a

upstream raw materials:

Methyltriphenylphosphonium bromide

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)-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

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

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