(2R,4aR,6S,7R,8aS)-4a,6-Dimethyl-7-[(2R,3S,4aR,8aS)-2-((S)-1-methyl-allyl)-octahydro-pyrano[3,2-b]pyran-3-yloxy]-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Base Information

• Chemical Name: (2R,4aR,6S,7R,8aS)-4a,6-Dimethyl-7-[(2R,3S,4aR,8aS)-2-((S)-1-methyl-allyl)-octahydro-pyrano[3,2-b]pyran-3-yloxy]-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxine
• CAS No.: 874211-88-8
• Molecular Formula: C₂₉H₄₀O₆
• Molecular Weight: 484.633

Synonyms:

Chemical Property of (2R,4aR,6S,7R,8aS)-4a,6-Dimethyl-7-[(2R,3S,4aR,8aS)-2-((S)-1-methyl-allyl)-octahydro-pyrano[3,2-b]pyran-3-yloxy]-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of (2R,4aR,6S,7R,8aS)-4a,6-Dimethyl-7-[(2R,3S,4aR,8aS)-2-((S)-1-methyl-allyl)-octahydro-pyrano[3,2-b]pyran-3-yloxy]-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxine

There total 12 articles about (2R,4aR,6S,7R,8aS)-4a,6-Dimethyl-7-[(2R,3S,4aR,8aS)-2-((S)-1-methyl-allyl)-octahydro-pyrano[3,2-b]pyran-3-yloxy]-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxine 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:

2-{(2R,4aR,6S,7R,8aS)-4a,6-Dimethyl-7-[(2R,3S,4aR,8aS)-2-((S)-1-methyl-allyl)-octahydro-pyrano[3,2-b]pyran-3-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl}-ethanol → (2R,4aR,6S,7R,8aS)-4a,6-Dimethyl-7-[(2R,3S,4aR,8aS)-2-((S)-1-methyl-allyl)-octahydro-pyrano[3,2-b]pyran-3-yloxy]-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxine (874211-88-8)

Guidance literature:

2-{(2R,4aR,6S,7R,8aS)-4a,6-Dimethyl-7-[(2R,3S,4aR,8aS)-2-((S)-1-methyl-allyl)-octahydro-pyrano[3,2-b]pyran-3-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl}-ethanol; With ortho-nitrophenyl selenocyanate; tributylphosphine; In tetrahydrofuran; at 20 ℃;

With dihydrogen peroxide; In tetrahydrofuran;

DOI:10.1016/j.tetlet.2005.10.136

Reference yield:

tert-Butyl-{2-[(2R,4aR,6S,7R,8aS)-4a,6-dimethyl-2-phenyl-7-((2R,3S,4aR,8aS)-2-vinyl-octahydro-pyrano[3,2-b]pyran-3-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-ethoxy}-diphenyl-silane (874211-78-6) → (2R,4aR,6S,7R,8aS)-4a,6-Dimethyl-7-[(2R,3S,4aR,8aS)-2-((S)-1-methyl-allyl)-octahydro-pyrano[3,2-b]pyran-3-yloxy]-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxine (874211-88-8)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 81 percent / O₂ / PdCl₂; CuCl / dimethylformamide; H₂O / 30 °C

2.1: PhNTf₂; KHMDS; DMPU / tetrahydrofuran / -78 °C

2.2: 74 percent / Pd(PPh₃)4 / tetrahydrofuran; dimethylformamide / 20 °C

3.1: DIBAL-H / CH₂Cl₂ / -78 °C

4.1: KH / tetrahydrofuran / 20 °C

5.1: BH₃*SMe₂ / tetrahydrofuran / 0 °C

5.2: 76 percent / H₂O₂; aq. NaOH / tetrahydrofuran / 0 °C

6.1: I₂; PPh₃; imidazole / benzene / 20 °C

7.1: t-BuLi / tetrahydrofuran / -78 °C

7.2: 86 percent / tetrahydrofuran; methanol

8.1: 84 percent / DDQ; NaHCO₃ / CH₂Cl₂; H₂O / 20 °C

9.1: SO₃*py; DMSO; Et₃N / CH₂Cl₂ / 20 °C

10.1: NaHMDS / tetrahydrofuran / 0 °C

11.1: TBAF / tetrahydrofuran / 20 °C

12.1: 2-nitrophenyl selenocyanate; PBu₃ / tetrahydrofuran / 20 °C

12.2: aq. H₂O₂ / tetrahydrofuran

With 1H-imidazole; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; N,N-phenylbistrifluoromethane-sulfonimide; ortho-nitrophenyl selenocyanate; pyridine-SO₃ complex; tributylphosphine; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; iodine; tert.-butyl lithium; oxygen; sodium hexamethyldisilazane; potassium hydride; potassium hexamethylsilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; copper(l) chloride; palladium dichloride; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; benzene; 1.1: Wacker oxidation / 10.1: Wittig olefination;

DOI:10.1016/j.tetlet.2005.10.136

Reference yield:

1-((2S,3S,4aR,8aS)-3-{(2R,4aR,6S,7R,8aS)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4a,6-dimethyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy}-octahydro-pyrano[3,2-b]pyran-2-yl)-ethanone (874211-79-7) → (2R,4aR,6S,7R,8aS)-4a,6-Dimethyl-7-[(2R,3S,4aR,8aS)-2-((S)-1-methyl-allyl)-octahydro-pyrano[3,2-b]pyran-3-yloxy]-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxine (874211-88-8)

Guidance literature:

Multi-step reaction with 11 steps

1.1: PhNTf₂; KHMDS; DMPU / tetrahydrofuran / -78 °C

1.2: 74 percent / Pd(PPh₃)4 / tetrahydrofuran; dimethylformamide / 20 °C

2.1: DIBAL-H / CH₂Cl₂ / -78 °C

3.1: KH / tetrahydrofuran / 20 °C

4.1: BH₃*SMe₂ / tetrahydrofuran / 0 °C

4.2: 76 percent / H₂O₂; aq. NaOH / tetrahydrofuran / 0 °C

5.1: I₂; PPh₃; imidazole / benzene / 20 °C

6.1: t-BuLi / tetrahydrofuran / -78 °C

6.2: 86 percent / tetrahydrofuran; methanol

7.1: 84 percent / DDQ; NaHCO₃ / CH₂Cl₂; H₂O / 20 °C

8.1: SO₃*py; DMSO; Et₃N / CH₂Cl₂ / 20 °C

9.1: NaHMDS / tetrahydrofuran / 0 °C

10.1: TBAF / tetrahydrofuran / 20 °C

11.1: 2-nitrophenyl selenocyanate; PBu₃ / tetrahydrofuran / 20 °C

11.2: aq. H₂O₂ / tetrahydrofuran

With 1H-imidazole; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; N,N-phenylbistrifluoromethane-sulfonimide; ortho-nitrophenyl selenocyanate; pyridine-SO₃ complex; tributylphosphine; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; iodine; tert.-butyl lithium; sodium hexamethyldisilazane; potassium hydride; potassium hexamethylsilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; benzene; 9.1: Wittig olefination;

DOI:10.1016/j.tetlet.2005.10.136

upstream raw materials:

tert-Butyl-{2-[(2R,4aR,6S,7R,8aS)-4a,6-dimethyl-2-phenyl-7-((2R,3S,4aR,8aS)-2-vinyl-octahydro-pyrano[3,2-b]pyran-3-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-ethoxy}-diphenyl-silane

1-((2S,3S,4aR,8aS)-3-{(2R,4aR,6S,7R,8aS)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4a,6-dimethyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy}-octahydro-pyrano[3,2-b]pyran-2-yl)-ethanone

tert-Butyl-(2-{(2R,4aR,6S,7R,8aS)-4a,6-dimethyl-7-[(2R,3S,4aR,8aS)-2-((S)-1-methyl-allyl)-octahydro-pyrano[3,2-b]pyran-3-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl}-ethoxy)-diphenyl-silane

(S)-2-((2R,3S,4aR,8aS)-3-{(2R,4aR,6S,7R,8aS)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4a,6-dimethyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy}-octahydro-pyrano[3,2-b]pyran-2-yl)-propan-1-ol

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