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

Base Information

• Chemical Name: 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
• CAS No.: 874211-87-7
• Molecular Formula: C₄₅H₆₀O₇Si
• Molecular Weight: 741.053

Synonyms:

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 10 articles about 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 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:

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) → 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 (874211-87-7)

Guidance literature:

Multi-step reaction with 10 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

With 1H-imidazole; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; N,N-phenylbistrifluoromethane-sulfonimide; pyridine-SO₃ complex; dimethylsulfide borane complex; 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:

(R)-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)-propionaldehyde + Methyltriphenylphosphonium bromide (1779-49-3) → 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 (874211-87-7)

Guidance literature:

With sodium hexamethyldisilazane; In tetrahydrofuran; at 0 ℃;

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) → 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 (874211-87-7)

Guidance literature:

Multi-step reaction with 9 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

With 1H-imidazole; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; N,N-phenylbistrifluoromethane-sulfonimide; pyridine-SO₃ complex; dimethylsulfide borane complex; 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:

Methyltriphenylphosphonium bromide

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

(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

Downstream raw materials:

(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

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