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

Base Information

Chemical Name: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
CAS No.:925453-61-8
Molecular Formula:C₃₅H₅₂O₁₄
Molecular Weight:696.789
Hs Code.:

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

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 24 articles about 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 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: 75.0%

: 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

: 925453-61-8
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

Guidance literature:: With chloro-trimethyl-silane; tetraethylammonium bromide; In dichloromethane; for 20h;
DOI:10.1002/anie.200352629

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 2 steps

1: 279 mg / CH₂Cl₂ / 48 h

2: 75 percent / TMSCl; Et₄NBr / CH₂Cl₂ / 0 - 20 °C

With chloro-trimethyl-silane; tetraethylammonium bromide; In dichloromethane;
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

: 925453-61-8
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

Guidance literature:: Multi-step reaction with 3 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

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