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

Base Information

Chemical Name: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
CAS No.:925453-22-1
Molecular Formula:C₃₅H₅₀O₁₄
Molecular Weight:694.774
Hs Code.:

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

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 25 articles about 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 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%

: 925453-61-8
tri-tert-butyl (1S,3S,4S,5R,6R,7R)-6-benzyloxy-7-(tert-butoxycarbonyl)oxy-4-hydroxy-1-(2-hydroxyethyl)-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate

: 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

Guidance literature:: With Dess-Martin periodane; In dichloromethane; for 24h;
DOI:10.1002/anie.200352629

Reference yield:

: 644981-53-3
tri-tert-butyl (1S,3S,4S,5R,6R,7R)-6-benzyloxy-7-(tert-butoxycarbonyl)oxy-4-hydroxy-1-[2-(methoxymethoxy)ethyl]-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate

: 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

Guidance literature:: Multi-step reaction with 2 steps

1: 75 percent / TMSCl; Et₄NBr / CH₂Cl₂ / 0 - 20 °C

2: 93 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

With chloro-trimethyl-silane; tetraethylammonium bromide; Dess-Martin periodane; In dichloromethane; 2: Dess-Martin oxidation;
DOI:10.1002/chem.200601212

Reference yield:

: (1S,3S,4S,5R,6R,7R)-6-Benzyloxy-7-tert-butoxycarbonyloxy-3-formyl-4-hydroxy-1-(2-methoxymethoxy-ethyl)-2,8-dioxa-bicyclo[3.2.1]octane-4,5-dicarboxylic acid di-tert-butyl ester

: 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

Guidance literature:: Multi-step reaction with 4 steps

1: NaH₂PO₄; NaClO₂ / 2-methyl-propan-2-ol; H₂O; various solvent(s) / 3 h / 20 °C

2: 279 mg / CH₂Cl₂ / 48 h

3: 75 percent / TMSCl; Et₄NBr / CH₂Cl₂ / 0 - 20 °C

4: 93 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

With sodium chlorite; sodium dihydrogenphosphate; chloro-trimethyl-silane; tetraethylammonium bromide; Dess-Martin periodane; In dichloromethane; water; tert-butyl alcohol; 4: Dess-Martin oxidation;
DOI:10.1002/chem.200601212