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

Base Information

• Chemical Name: 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
• CAS No.: 925453-73-2
• Molecular Formula: C₄₀H₆₂O₁₅
• Molecular Weight: 782.923
• Mol file: 925453-73-2.mol

Synonyms:

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 7 articles about 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 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:

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 → 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 (925453-73-2)

Guidance literature:

Multi-step reaction with 4 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

With dmap; potassium fluoride; 2,2'-azobis(isobutyronitrile); 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

Reference yield:

6-benzyloxy-7-tert-butoxycarbonyloxy-1-{2-[2,2-dimethyl-5-(1-methyl-2-phenyl-ethyl)-[1,2]oxasilolan-4-yl]-ethyl}-4-hydroxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl ester (925453-70-9) → 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 (925453-73-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 102 mg / NaHCO₃; KF; aq. H₂O₂ / tetrahydrofuran; methanol / 24 h

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

With potassium fluoride; dihydrogen peroxide; sodium hydrogencarbonate; palladium dihydroxide; pyrographite; In tetrahydrofuran; methanol; ethyl acetate; 1: Tamao oxidation;

DOI:10.1002/chem.200601212

Reference yield:

tri-tert-butyl [1S,1(2E,4S,5R),3S,4S,5R,6R,7R]-6-benzyloxy-1-[4-[(bromomethyl)dimethylsilyl]oxy-5-methyl-6-phenyl-2-hexenyl]-7-(tert-butoxycarbonyl)oxy-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate (925453-69-6) → 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 (925453-73-2)

Guidance literature:

Multi-step reaction with 3 steps

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

2: 102 mg / NaHCO₃; KF; aq. H₂O₂ / tetrahydrofuran; methanol / 24 h

3: 95 percent / Pd(OH)2/carbon / ethyl acetate / 13 h / 760 Torr

With potassium fluoride; 2,2'-azobis(isobutyronitrile); dihydrogen peroxide; tri-n-butyl-tin hydride; sodium hydrogencarbonate; palladium dihydroxide; pyrographite; In tetrahydrofuran; methanol; ethyl acetate; benzene; 2: Tamao oxidation;

DOI:10.1002/chem.200601212

upstream raw materials:

6-benzyloxy-7-tert-butoxycarbonyloxy-1-{2-[2,2-dimethyl-5-(1-methyl-2-phenyl-ethyl)-[1,2]oxasilolan-4-yl]-ethyl}-4-hydroxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl ester

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

(2S,3R)-1,2-epoxy-3-methyl-4-phenylbutane

(3R,4R)-4-methyl-5-phenyl-1-penten-3-ol

Downstream raw materials:

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

zaragozic acid A

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

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