3,4,5,6-tetra-O-benzyl-2-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-(1->2)-L-myo-inositol

Base Information

• Chemical Name: 3,4,5,6-tetra-O-benzyl-2-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-(1->2)-L-myo-inositol
• CAS No.: 170900-79-5
• Molecular Formula: C₆₈H₇₀O₁₁
• Molecular Weight: 1063.3
• Mol file: 170900-79-5.mol

Synonyms:3,4,5,6-tetra-O-benzyl-2-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-(1->2)-L-myo-inositol

Chemical Property of 3,4,5,6-tetra-O-benzyl-2-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-(1->2)-L-myo-inositol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,4,5,6-tetra-O-benzyl-2-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-(1->2)-L-myo-inositol

There total 9 articles about 3,4,5,6-tetra-O-benzyl-2-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-(1->2)-L-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: 94.0%

3,4,5,6-tetra-O-benzyl-1-O-(4-methoxybenzyl)-2-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-(1->2)-L-myo-inositol (579494-16-9) → 3,4,5,6-tetra-O-benzyl-2-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-(1->2)-L-myo-inositol (170900-79-5)

Guidance literature:

With ammonium cerium(IV) nitrate; In water; toluene; acetonitrile; at 0 - 20 ℃;

DOI:10.1016/j.carres.2003.06.002

Reference yield:

benzyl bromide (100-39-0) → 3,4,5,6-tetra-O-benzyl-2-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-(1->2)-L-myo-inositol (170900-79-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 84 percent / sodium hydride / dimethylformamide / 4 h / 20 °C

2.1: 95 percent / camphor-10-sulfonic acid / CH₂Cl₂; methanol / 24 h / 20 °C

3.1: dibutyltin oxide / toluene / 3 h / Heating

3.2: 79 percent / tetrabutylammonium iodide / toluene / 1.5 h / 110 °C

4.1: trimethylsilyl triflate / diethyl ether / 0 h / 20 °C

5.1: methylamine / ethanol / 6 h / 20 °C

6.1: (Ph₃P)3RhCl; DBU / ethanol / 1.5 h / Heating

6.2: 87 percent / HCl / acetone / 0.25 h / Heating

7.1: 86 percent / NaOH / dimethylformamide / 3 h / 20 °C

8.1: 94 percent / ceric(IV)ammonium nitrate / acetonitrile; toluene; H₂O / 0 - 20 °C

With sodium hydroxide; Wilkinson's catalyst; ammonium cerium(IV) nitrate; trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; sodium hydride; di(n-butyl)tin oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; methylamine; In methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1016/j.carres.2003.06.002

Reference yield:

1D-4-O-allyl-1,5,6-tri-O-benzyl-myo-inositol (131233-71-1,1214020-75-3) → 3,4,5,6-tetra-O-benzyl-2-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-(1->2)-L-myo-inositol (170900-79-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: dibutyltin oxide / toluene / 3 h / Heating

1.2: 79 percent / tetrabutylammonium iodide / toluene / 1.5 h / 110 °C

2.1: trimethylsilyl triflate / diethyl ether / 0 h / 20 °C

3.1: methylamine / ethanol / 6 h / 20 °C

4.1: (Ph₃P)3RhCl; DBU / ethanol / 1.5 h / Heating

4.2: 87 percent / HCl / acetone / 0.25 h / Heating

5.1: 86 percent / NaOH / dimethylformamide / 3 h / 20 °C

6.1: 94 percent / ceric(IV)ammonium nitrate / acetonitrile; toluene; H₂O / 0 - 20 °C

With sodium hydroxide; Wilkinson's catalyst; ammonium cerium(IV) nitrate; trimethylsilyl trifluoromethanesulfonate; di(n-butyl)tin oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; methylamine; In diethyl ether; ethanol; water; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1016/j.carres.2003.06.002

upstream raw materials:

benzyl bromide

2-O-acetyl-3,4,6-tri-O-benzyl-α/β-D-mannopyranosyl fluoride

3,4,5,6-tetra-O-benzyl-1-O-(4-methoxybenzyl)-2-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-(1->2)-L-myo-inositol

1D-4-O-allyl-1,5,6-tri-O-benzyl-myo-inositol