6-O-allyl-3,4,5-tri-O-benzyl-1-O-(1R)-menthyloxycarbonyl-2-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-D-myo-inositol

Base Information

Chemical Name:6-O-allyl-3,4,5-tri-O-benzyl-1-O-(1R)-menthyloxycarbonyl-2-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-D-myo-inositol
CAS No.:579493-76-8
Molecular Formula:C₇₅H₈₆O₁₃
Molecular Weight:1195.5
Hs Code.:

Synonyms:6-O-allyl-3,4,5-tri-O-benzyl-1-O-(1R)-menthyloxycarbonyl-2-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-D-myo-inositol

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Chemical Property of 6-O-allyl-3,4,5-tri-O-benzyl-1-O-(1R)-menthyloxycarbonyl-2-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-D-myo-inositol

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Technology Process of 6-O-allyl-3,4,5-tri-O-benzyl-1-O-(1R)-menthyloxycarbonyl-2-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-D-myo-inositol

There total 4 articles about 6-O-allyl-3,4,5-tri-O-benzyl-1-O-(1R)-menthyloxycarbonyl-2-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-D-myo-inositol 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: 85.0%

: 100-39-0
benzyl bromide

: 579493-75-7
6-O-allyl-4,5-di-O-benzyl-1-O-(1R)-menthyloxycarbonyl-2-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-D-myo-inositol

: 579493-76-8
6-O-allyl-3,4,5-tri-O-benzyl-1-O-(1R)-menthyloxycarbonyl-2-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-D-myo-inositol

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 2.5h;
DOI:10.1016/j.carres.2003.06.002

Reference yield:

: 380366-30-3
6-O-allyl-2,3:4,5-di-O-cyclohexylidene-1-O-(1R)-menthyloxycarbonyl-D-myo-inositol

: 579493-76-8
6-O-allyl-3,4,5-tri-O-benzyl-1-O-(1R)-menthyloxycarbonyl-2-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-D-myo-inositol

Guidance literature:: Multi-step reaction with 7 steps

1: 68 percent / pyridinium p-toluenesulfonate; p-toluenesulfonic acid / CH₂Cl₂; methanol / 1.17 h / 45 °C

2: 71 percent / silver(I) oxide / CH₂Cl₂ / 3 h / 20 °C

3: 89 percent / camphor-10-sulfonic acid / CH₂Cl₂; methanol / 8.5 h / 45 °C

4: 65 percent / K₂CO₃; dimethyltin dichloride / tetrahydrofuran / 20 °C

5: 95 percent / tin(II) trifluoromethanesulfonate / diethyl ether / 1 h / 20 °C

6: 79 percent / dimethylamine / ethanol / 24 h / 20 °C

7: 85 percent / sodium hydride / dimethylformamide / 2.5 h / 20 °C

With tin(II) trifluoromethanesulfonate; camphor-10-sulfonic acid; dimethyltin dichloride; pyridinium p-toluenesulfonate; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; dimethyl amine; silver(l) oxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.carres.2003.06.002

Reference yield:

: 579493-70-2
6-O-allyl-2,3-O-cyclohexylidene-1-O-(1R)-menthyloxycarbonyl-D-myo-inositol

: 579493-76-8
6-O-allyl-3,4,5-tri-O-benzyl-1-O-(1R)-menthyloxycarbonyl-2-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-D-myo-inositol

Guidance literature:: Multi-step reaction with 6 steps

1: 71 percent / silver(I) oxide / CH₂Cl₂ / 3 h / 20 °C

2: 89 percent / camphor-10-sulfonic acid / CH₂Cl₂; methanol / 8.5 h / 45 °C

3: 65 percent / K₂CO₃; dimethyltin dichloride / tetrahydrofuran / 20 °C

4: 95 percent / tin(II) trifluoromethanesulfonate / diethyl ether / 1 h / 20 °C

5: 79 percent / dimethylamine / ethanol / 24 h / 20 °C

6: 85 percent / sodium hydride / dimethylformamide / 2.5 h / 20 °C

With tin(II) trifluoromethanesulfonate; camphor-10-sulfonic acid; dimethyltin dichloride; sodium hydride; potassium carbonate; dimethyl amine; silver(l) oxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.carres.2003.06.002