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

Base Information

Chemical Name:tri(tert-butyl) [1S,1(4R,5R),3S,4S,5R,6R,7R]-6,7-diacetoxy-1-(4-acetoxy-5-methyl-6-phenylhexyl)-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate
CAS No.:164215-53-6
Molecular Formula:C₄₀H₅₈O₁₅
Molecular Weight:778.892
Hs Code.:

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

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

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

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

There total 72 articles about tri(tert-butyl) [1S,1(4R,5R),3S,4S,5R,6R,7R]-6,7-diacetoxy-1-(4-acetoxy-5-methyl-6-phenylhexyl)-4-hydroxy-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: 100.0%

: 108-24-7
acetic anhydride

: 191935-36-1
tri(tert-butyl) [1S,1(4R,5R),3S,4S,5R,6R,7R]-4,6,7-trihydroxy-1-(4-hydroxy-5-methyl-6-phenylhexyl)-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate

: 164215-53-6
tri(tert-butyl) [1S,1(4R,5R),3S,4S,5R,6R,7R]-6,7-diacetoxy-1-(4-acetoxy-5-methyl-6-phenylhexyl)-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate

Guidance literature:: With dmap; In dichloromethane; at 0 ℃; for 0.5h;
DOI:10.1016/j.tet.2005.09.030

Reference yield:

: 164215-43-4
(1S,3R,4S,5R,6R,7R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxymethyl)-4-ethynyl-1-((4R,5R)-4-hydroxy-5-methyl-6-phenyl-hexyl)-2,8-dioxa-bicyclo[3.2.1]octane-4,6,7-triol

: 164215-53-6
tri(tert-butyl) [1S,1(4R,5R),3S,4S,5R,6R,7R]-6,7-diacetoxy-1-(4-acetoxy-5-methyl-6-phenylhexyl)-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate

Guidance literature:: Multi-step reaction with 13 steps

1: 94 percent / 4-DMAP / CH₂Cl₂ / 12 h

2: 90 percent / Cl₂CHCO₂H / methanol / 7 h

3: H₂ / 5percent Pd/C / pyridine / 2 h / 760 Torr

4: 94 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 23 °C

5: aq. NaClO₂ / 2-methyl-propan-2-ol; various solvent(s) / 3 h / 10 °C

6: CH₂Cl₂ / 22 h

7: 90 percent / HF*pyridine / tetrahydrofuran

8: 84 percent / Dess-Martin periodinane, pyridine / CH₂Cl₂ / 0.58 h / 23 °C

9: aq. NaClO₂ / 2-methyl-propan-2-ol; various solvent(s) / 3 h / 10 °C

10: CH₂Cl₂ / 22 h

11: 1.) O₃ / 1.) CH₂Cl₂, MeOH

12: aq. NaClO2, NaH2PO4, β-isoamylene / tetrahydrofuran

13: CH₂Cl₂

With pyridine; dichloro-acetic acid; dmap; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; hydrogen; Dess-Martin periodane; pyridine hydrogenfluoride; ozone; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane; tert-butyl alcohol;
DOI:10.1021/ja00136a008

Reference yield:

: 164215-42-3
2,2-Dimethyl-propionic acid (1S,3R,4S,5R,6R,7R)-3,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-7-(2,2-dimethyl-propionyloxy)-1-[(4R,5R)-4-(2,2-dimethyl-propionyloxy)-5-methyl-6-phenyl-hexyl]-4-ethynyl-4-hydroxy-2,8-dioxa-bicyclo[3.2.1]oct-6-yl ester

: 164215-53-6
tri(tert-butyl) [1S,1(4R,5R),3S,4S,5R,6R,7R]-6,7-diacetoxy-1-(4-acetoxy-5-methyl-6-phenylhexyl)-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate

Guidance literature:: Multi-step reaction with 14 steps

1: 84 percent / Dibal-H / CH₂Cl₂; toluene / 5.5 h / -78 - -5 °C

2: 94 percent / 4-DMAP / CH₂Cl₂ / 12 h

3: 90 percent / Cl₂CHCO₂H / methanol / 7 h

4: H₂ / 5percent Pd/C / pyridine / 2 h / 760 Torr

5: 94 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 23 °C

6: aq. NaClO₂ / 2-methyl-propan-2-ol; various solvent(s) / 3 h / 10 °C

7: CH₂Cl₂ / 22 h

8: 90 percent / HF*pyridine / tetrahydrofuran

9: 84 percent / Dess-Martin periodinane, pyridine / CH₂Cl₂ / 0.58 h / 23 °C

10: aq. NaClO₂ / 2-methyl-propan-2-ol; various solvent(s) / 3 h / 10 °C

11: CH₂Cl₂ / 22 h

12: 1.) O₃ / 1.) CH₂Cl₂, MeOH

13: aq. NaClO2, NaH2PO4, β-isoamylene / tetrahydrofuran

14: CH₂Cl₂

With pyridine; dichloro-acetic acid; dmap; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; hydrogen; diisobutylaluminium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; ozone; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane; toluene; tert-butyl alcohol;
DOI:10.1021/ja00136a008