(5R,6R,7S,8S)-7,8-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-6-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyloxy)imidazo[1,2-a]pyridine

Base Information

Chemical Name:(5R,6R,7S,8S)-7,8-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-6-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyloxy)imidazo[1,2-a]pyridine
CAS No.:244036-98-4
Molecular Formula:C₆₃H₆₄N₂O₉
Molecular Weight:993.209
Hs Code.:

Synonyms:(5R,6R,7S,8S)-7,8-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-6-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyloxy)imidazo[1,2-a]pyridine

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Chemical Property of (5R,6R,7S,8S)-7,8-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-6-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyloxy)imidazo[1,2-a]pyridine

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Technology Process of (5R,6R,7S,8S)-7,8-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-6-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyloxy)imidazo[1,2-a]pyridine

There total 8 articles about (5R,6R,7S,8S)-7,8-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-6-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyloxy)imidazo[1,2-a]pyridine 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: 77.0%

: 244037-02-3
(5R,6R,7S,8S)-7,8-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-2-iodo-6-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyloxy)imidazo[1,2-a]pyridine

: 244036-98-4
(5R,6R,7S,8S)-7,8-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-6-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyloxy)imidazo[1,2-a]pyridine

Guidance literature:: With ethylmagnesium bromide; In tetrahydrofuran; diethyl ether; at 0 ℃; for 0.25h;
DOI:10.1002/(SICI)1522-2675(19990707)82:7<963::AID-HLCA963>3.0.CO;2-V

Reference yield:

: 22483-09-6
2,2-dimethoxyethylamine

: 244036-97-3
5-amino-2,3,6-tri-O-benzyl-5-deoxy-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-1-thio-D-gluconolactam

: (5R,6R,7S,8R)-7,8-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-6-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyloxy)imidazo[1,2-a]pyridine

: 244036-98-4
(5R,6R,7S,8S)-7,8-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-6-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyloxy)imidazo[1,2-a]pyridine

Guidance literature:: 2,2-dimethoxyethylamine; 5-amino-2,3,6-tri-O-benzyl-5-deoxy-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-1-thio-D-gluconolactam; With mercury(II) diacetate; In tetrahydrofuran; at 0 ℃; for 2h;

With toluene-4-sulfonic acid; In toluene; at 60 ℃; Title compound not separated from byproducts;
DOI:10.1002/(SICI)1522-2675(19990707)82:7<963::AID-HLCA963>3.0.CO;2-V

Reference yield:

: 148968-90-5
2,3,6-tris-O-(phenylmethyl)-4-O-[2,3,4,6-tetrakis-O-(phenylmethyl)-β-D-glucopyranosyl]-D-glucopyranoside

: 244036-98-4
(5R,6R,7S,8S)-7,8-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-6-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyloxy)imidazo[1,2-a]pyridine

Guidance literature:: Multi-step reaction with 5 steps

1.1: 21.7 g / Dess-Martin periodinane / CH₂Cl₂ / 5 h / 23 °C

2.1: 21.8 g / NH₃ / CH₂Cl₂ / 2 h / Heating

3.1: 1-hydroxy-1,2-benzodioxol-3(1H)-one 1-oxide / dimethylsulfoxide / 5 h / 23 °C

3.2: sodium cyanoborohydride / acetonitrile; formic acid / 5 h / 35 °C

4.1: 87 percent / Lawesson's reagent / toluene / 2 h / 40 °C

5.1: Hg(OAc)2 / tetrahydrofuran / 2 h / 0 °C

5.2: TsOH*H₂O / toluene / 60 °C

With Lawessons reagent; mercury(II) diacetate; ammonia; Dess-Martin periodane; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; toluene; 1.1: Oxidation / 2.1: amidation / 3.1: Oxidation / 3.2: Reduction / 4.1: thionation / 5.1: Substitution / 5.2: Substitution;
DOI:10.1002/(SICI)1522-2675(19990707)82:7<963::AID-HLCA963>3.0.CO;2-V