1,6-anhydro-2,3-di-O-benzyl-4-O-(2,3,4-tri-O-benzyl-α-L-idopyranosyl)-β-D-glucopyranose

Base Information

Chemical Name:1,6-anhydro-2,3-di-O-benzyl-4-O-(2,3,4-tri-O-benzyl-α-L-idopyranosyl)-β-D-glucopyranose
CAS No.:86032-70-4
Molecular Formula:C₄₇H₅₀O₁₀
Molecular Weight:774.908
Hs Code.:

Synonyms:

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Chemical Property of 1,6-anhydro-2,3-di-O-benzyl-4-O-(2,3,4-tri-O-benzyl-α-L-idopyranosyl)-β-D-glucopyranose

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Technology Process of 1,6-anhydro-2,3-di-O-benzyl-4-O-(2,3,4-tri-O-benzyl-α-L-idopyranosyl)-β-D-glucopyranose

There total 8 articles about 1,6-anhydro-2,3-di-O-benzyl-4-O-(2,3,4-tri-O-benzyl-α-L-idopyranosyl)-β-D-glucopyranose 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:

: 38631-27-5
2,3-Di-O-acetyl-1,6-anhydro-4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranose

: 86032-70-4
1,6-anhydro-2,3-di-O-benzyl-4-O-(2,3,4-tri-O-benzyl-α-L-idopyranosyl)-β-D-glucopyranose

Guidance literature:: Multi-step reaction with 8 steps

1: NaOMe / methanol / 10 h / Ambient temperature

2: pyridine / 10 h

3: NaH / dimethylformamide / 2 h / Ambient temperature

4: 79 percent / aq. HClO₄ / CHCl₃ / 0.08 h / Ambient temperature

5: 89 percent / 4-(dimethylamino)pyridine / pyridine / 10 h / Ambient temperature

6: 84 percent / NaI / butan-2-one / 10 h / Heating

7: 98 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / tetrahydrofuran / 10 h / Heating

8: 1) tetrabutylammonium borohydride, methyl iodide, 2) H₂O₂, aq. NaOH / 1) CH₂Cl₂, 3 h, room temp.; 2) CH₂Cl₂, 3h, room temp.

With dmap; sodium hydroxide; perchloric acid; dihydrogen peroxide; sodium methylate; sodium hydride; tetrabutylammonium borohydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium iodide; methyl iodide; In tetrahydrofuran; pyridine; methanol; chloroform; N,N-dimethyl-formamide; butanone;
DOI:10.1016/0008-6215(83)88140-3

Reference yield:

: 86032-66-8
O-(2,3,4-tri-O-benzyl-β-D-galactopyranosyl)-(1->4)-1,6-anhydro-2,3-di-O-benzyl-β-D-glucopyranose

: 86032-70-4
1,6-anhydro-2,3-di-O-benzyl-4-O-(2,3,4-tri-O-benzyl-α-L-idopyranosyl)-β-D-glucopyranose

Guidance literature:: Multi-step reaction with 4 steps

1: 89 percent / 4-(dimethylamino)pyridine / pyridine / 10 h / Ambient temperature

2: 84 percent / NaI / butan-2-one / 10 h / Heating

3: 98 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / tetrahydrofuran / 10 h / Heating

4: 1) tetrabutylammonium borohydride, methyl iodide, 2) H₂O₂, aq. NaOH / 1) CH₂Cl₂, 3 h, room temp.; 2) CH₂Cl₂, 3h, room temp.

With dmap; sodium hydroxide; dihydrogen peroxide; tetrabutylammonium borohydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium iodide; methyl iodide; In tetrahydrofuran; pyridine; butanone;
DOI:10.1016/0008-6215(83)88140-3

Reference yield:

: 86032-68-0
1,6-anhydro-2,3-di-O-benzyl-4-O-(2,3,4-tri-O-benzyl-6-deoxy-6-iodo-β-D-glucopyranosyl)-β-D-glucopyranose

: 86032-70-4
1,6-anhydro-2,3-di-O-benzyl-4-O-(2,3,4-tri-O-benzyl-α-L-idopyranosyl)-β-D-glucopyranose

Guidance literature:: Multi-step reaction with 2 steps

1: 98 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / tetrahydrofuran / 10 h / Heating

2: 1) tetrabutylammonium borohydride, methyl iodide, 2) H₂O₂, aq. NaOH / 1) CH₂Cl₂, 3 h, room temp.; 2) CH₂Cl₂, 3h, room temp.

With sodium hydroxide; dihydrogen peroxide; tetrabutylammonium borohydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; methyl iodide; In tetrahydrofuran;
DOI:10.1016/0008-6215(83)88140-3