(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

Base Information

• Chemical Name: (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
• CAS No.: 874211-94-6
• Molecular Formula: C₄₄H₆₀O₈Si
• Molecular Weight: 745.041

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 8 articles about (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 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: 84.0%

tert-Butyl-[2-((2R,4aR,6S,7R,8aS)-7-{(2R,3S,4aR,8aS)-2-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-octahydro-pyrano[3,2-b]pyran-3-yloxy}-4a,6-dimethyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-ethoxy]-diphenyl-silane (874211-86-6) → (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 (874211-94-6)

Guidance literature:

With sodium hydrogencarbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 20 ℃;

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) → (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 (874211-94-6)

Guidance literature:

Multi-step reaction with 8 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

With 1H-imidazole; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; N,N-phenylbistrifluoromethane-sulfonimide; dimethylsulfide borane complex; iodine; tert.-butyl lithium; oxygen; potassium hydride; potassium hexamethylsilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; 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;

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) → (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 (874211-94-6)

Guidance literature:

Multi-step reaction with 7 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

With 1H-imidazole; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; N,N-phenylbistrifluoromethane-sulfonimide; dimethylsulfide borane complex; iodine; tert.-butyl lithium; potassium hydride; potassium hexamethylsilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; benzene;

DOI:10.1016/j.tetlet.2005.10.136

upstream raw materials:

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

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

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)-acrylic acid methyl ester

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

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

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