(1S,2R,8R,8aR)-2,8-bis(benzyloxy)-1-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyloxy)-hexahydroindolizin-5(1H)-one

Base Information

Chemical Name:(1S,2R,8R,8aR)-2,8-bis(benzyloxy)-1-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyloxy)-hexahydroindolizin-5(1H)-one
CAS No.:1393529-13-9
Molecular Formula:C₅₁H₅₅NO₁₀
Molecular Weight:841.998
Hs Code.:

Synonyms:(1S,2R,8R,8aR)-2,8-bis(benzyloxy)-1-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyloxy)-hexahydroindolizin-5(1H)-one

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Chemical Property of (1S,2R,8R,8aR)-2,8-bis(benzyloxy)-1-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyloxy)-hexahydroindolizin-5(1H)-one

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Technology Process of (1S,2R,8R,8aR)-2,8-bis(benzyloxy)-1-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyloxy)-hexahydroindolizin-5(1H)-one

There total 2 articles about (1S,2R,8R,8aR)-2,8-bis(benzyloxy)-1-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyloxy)-hexahydroindolizin-5(1H)-one 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: 27.0%

: 1393529-11-7
(1S,2R,8R,8aS)-2,8-bis(benzyloxy)-1-hydroxyhexahydroindolizin-5(1H)-one

: 441017-58-9
6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl iodide

: 1393529-13-9
(1S,2R,8R,8aR)-2,8-bis(benzyloxy)-1-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyloxy)-hexahydroindolizin-5(1H)-one

Guidance literature:: With tetra-(n-butyl)ammonium iodide; 2,4,6-tri-tert-butylpyrimidine; In toluene; at 55 ℃; for 96h; Inert atmosphere; Molecular sieve;
DOI:10.1016/j.tetasy.2012.06.011

Reference yield:

: 159701-87-8
(3aR,9R,9aR,9bS)-9-benzyloxy-2,2-dimethylhexahydro-[1,3]dioxolo[4,5-a]indolizin-6(9bH)-one

: 1393529-13-9
(1S,2R,8R,8aR)-2,8-bis(benzyloxy)-1-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyloxy)-hexahydroindolizin-5(1H)-one

Guidance literature:: Multi-step reaction with 3 steps

1: toluene-4-sulfonic acid / methanol / 26 h / Inert atmosphere; Reflux

2: tetra-(n-butyl)ammonium iodide; sodium hydride / tetrahydrofuran / 18.5 h / 0 - 20 °C / Inert atmosphere

3: tetra-(n-butyl)ammonium iodide; 2,4,6-tri-tert-butylpyrimidine / toluene / 96 h / 55 °C / Inert atmosphere; Molecular sieve

With tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; 2,4,6-tri-tert-butylpyrimidine; In tetrahydrofuran; methanol; toluene;
DOI:10.1016/j.tetasy.2012.06.011