tri-tert-butyl [1S,1(3S,4S,5R),3S,4S,5R,6R,7R]-7-(tert-butoxycarbonyl)oxy-4,6-dihydroxy-1-[4-hydroxy-5-methyl-3-[(2-nitrophenylseleno)methyl]-6-phenylhexyl]-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate

Base Information

Chemical Name:tri-tert-butyl [1S,1(3S,4S,5R),3S,4S,5R,6R,7R]-7-(tert-butoxycarbonyl)oxy-4,6-dihydroxy-1-[4-hydroxy-5-methyl-3-[(2-nitrophenylseleno)methyl]-6-phenylhexyl]-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate
CAS No.:925453-74-3
Molecular Formula:C₄₆H₆₅NO₁₆Se
Molecular Weight:966.979
Hs Code.:

tri-tert-butyl [1S,1(3S,4S,5R),3S,4S,5R,6R,7R]-7-(tert-butoxycarbonyl)oxy-4,6-dihydroxy-1-[4-hydroxy-5-methyl-3-[(2-nitrophenylseleno)methyl]-6-phenylhexyl]-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate

Synonyms:tri-tert-butyl [1S,1(3S,4S,5R),3S,4S,5R,6R,7R]-7-(tert-butoxycarbonyl)oxy-4,6-dihydroxy-1-[4-hydroxy-5-methyl-3-[(2-nitrophenylseleno)methyl]-6-phenylhexyl]-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate

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Chemical Property of tri-tert-butyl [1S,1(3S,4S,5R),3S,4S,5R,6R,7R]-7-(tert-butoxycarbonyl)oxy-4,6-dihydroxy-1-[4-hydroxy-5-methyl-3-[(2-nitrophenylseleno)methyl]-6-phenylhexyl]-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate

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Technology Process of tri-tert-butyl [1S,1(3S,4S,5R),3S,4S,5R,6R,7R]-7-(tert-butoxycarbonyl)oxy-4,6-dihydroxy-1-[4-hydroxy-5-methyl-3-[(2-nitrophenylseleno)methyl]-6-phenylhexyl]-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate

There total 9 articles about tri-tert-butyl [1S,1(3S,4S,5R),3S,4S,5R,6R,7R]-7-(tert-butoxycarbonyl)oxy-4,6-dihydroxy-1-[4-hydroxy-5-methyl-3-[(2-nitrophenylseleno)methyl]-6-phenylhexyl]-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate 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: 62.0%

: 925453-73-2
tri-tert-butyl [1S,1(3R,4S,5R),3S,4S,5R,6R,7R]-7-(tert-butoxycarbonyl)oxy-4,6-dihydroxy-1-[4-hydroxy-3-(hydroxymethyl)-5-methyl-6-phenylhexyl]-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate

: 51694-22-5
ortho-nitrophenyl selenocyanate

: 925453-74-3
tri-tert-butyl [1S,1(3S,4S,5R),3S,4S,5R,6R,7R]-7-(tert-butoxycarbonyl)oxy-4,6-dihydroxy-1-[4-hydroxy-5-methyl-3-[(2-nitrophenylseleno)methyl]-6-phenylhexyl]-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate

Guidance literature:: With tributylphosphine; In tetrahydrofuran; for 0.5h;
DOI:10.1002/chem.200601212

Reference yield:

: 925453-71-0
tri-tert-butyl [1S,1(3R,4S,5R),3S,4S,5R,6R,7R]-6-benzyloxy-7-(tert-butoxycarbonyl)oxy-4-hydroxy-1-[4-hydroxy-3-(hydroxymethyl)-5-methyl-6-phenylhexyl]-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate

: 925453-74-3
tri-tert-butyl [1S,1(3S,4S,5R),3S,4S,5R,6R,7R]-7-(tert-butoxycarbonyl)oxy-4,6-dihydroxy-1-[4-hydroxy-5-methyl-3-[(2-nitrophenylseleno)methyl]-6-phenylhexyl]-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: 95 percent / Pd(OH)2/carbon / ethyl acetate / 13 h / 760 Torr

2: 62 percent / Bu₃P / tetrahydrofuran / 0.5 h

With tributylphosphine; palladium dihydroxide; pyrographite; In tetrahydrofuran; ethyl acetate;
DOI:10.1002/chem.200601212

Reference yield:

: tri-tert-butyl [1S,1(2E,4S,5R),3S,4S,5R,6R,7R]-6-benzyloxy-7-(tert-butoxycarbonyl)oxy-4-hydroxy-1-(4-hydroxy-5-methyl-6-phenyl-2-hexenyl)-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate

: 925453-74-3
tri-tert-butyl [1S,1(3S,4S,5R),3S,4S,5R,6R,7R]-7-(tert-butoxycarbonyl)oxy-4,6-dihydroxy-1-[4-hydroxy-5-methyl-3-[(2-nitrophenylseleno)methyl]-6-phenylhexyl]-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: 96 percent / Et₃N; 4-(dimethylamino)pyridine / CH₂Cl₂ / 1 h / 0 °C

2: Bu₃SnH; 2,2'-azobisisobutyronitrile / benzene / 1 h / Heating

3: 102 mg / NaHCO₃; KF; aq. H₂O₂ / tetrahydrofuran; methanol / 24 h

4: 95 percent / Pd(OH)2/carbon / ethyl acetate / 13 h / 760 Torr

5: 62 percent / Bu₃P / tetrahydrofuran / 0.5 h

With dmap; potassium fluoride; 2,2'-azobis(isobutyronitrile); tributylphosphine; dihydrogen peroxide; tri-n-butyl-tin hydride; sodium hydrogencarbonate; triethylamine; palladium dihydroxide; pyrographite; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; benzene; 3: Tamao oxidation;
DOI:10.1002/chem.200601212