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

Base Information

Chemical Name:tri-tert-butyl (1S,3S,4S,5R,6R,7R)-1-allyl-6-benzyloxy-7-(tert-butoxycarbonyl)oxy-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate
CAS No.:925453-62-9
Molecular Formula:C₃₆H₅₂O₁₃
Molecular Weight:692.801
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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

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

There total 11 articles about tri-tert-butyl (1S,3S,4S,5R,6R,7R)-1-allyl-6-benzyloxy-7-(tert-butoxycarbonyl)oxy-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: 93.0%

: 1779-49-3
Methyltriphenylphosphonium bromide

: 925453-22-1
tri-tert-butyl (1S,3S,4S,5R,6R,7R)-6-benzyloxy-7-(tert-butoxycarbonyl)oxy-1-(formylmethyl)-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate

: 925453-62-9
tri-tert-butyl (1S,3S,4S,5R,6R,7R)-1-allyl-6-benzyloxy-7-(tert-butoxycarbonyl)oxy-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate

Guidance literature:: With potassium tert-butylate; In diethyl ether; at 20 ℃; for 0.5h;
DOI:10.1002/chem.200601212

Reference yield: 62.0%

: 1286209-89-9
C₂₉H₄₆O₁₃

: 100-39-0
benzyl bromide

: 925453-62-9
tri-tert-butyl (1S,3S,4S,5R,6R,7R)-1-allyl-6-benzyloxy-7-(tert-butoxycarbonyl)oxy-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate

Guidance literature:: With silver(l) oxide; In toluene; at 20 - 40 ℃; chemoselective reaction;
DOI:10.1002/chem.201003399

Reference yield:

: 1286209-84-4
C₅₁H₆₂O₁₅SSi

: 925453-62-9
tri-tert-butyl (1S,3S,4S,5R,6R,7R)-1-allyl-6-benzyloxy-7-(tert-butoxycarbonyl)oxy-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate

Guidance literature:: Multi-step reaction with 6 steps

1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / benzene / 3 h / Reflux

2: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 5 h / 0 - 20 °C

3: methanol; potassium carbonate / 2.5 h / 16 °C

4: 4-pyrrolidin-1-ylpyridine; triethylamine / dichloromethane / 17.5 h / -3 °C

5: quinoline; hydrogen / benzene / 8 h / 20 °C / 750.08 Torr

6: silver(l) oxide / toluene / 20 - 40 °C

With quinoline; methanol; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; potassium carbonate; 4-pyrrolidin-1-ylpyridine; acetic acid; triethylamine; silver(l) oxide; In tetrahydrofuran; dichloromethane; toluene; benzene; 5: Lindlar semi-hydrogenation;
DOI:10.1002/chem.201003399