(-)-2,4,5,6-tetra-O-benzyl-1-O-(p-methoxybenzyl)-3-deoxy-3-azidomethyl-myo-inositol

Base Information

Chemical Name:(-)-2,4,5,6-tetra-O-benzyl-1-O-(p-methoxybenzyl)-3-deoxy-3-azidomethyl-myo-inositol
CAS No.:403651-42-3
Molecular Formula:C₄₃H₄₅N₃O₆
Molecular Weight:699.847
Hs Code.:

Synonyms:(-)-2,4,5,6-tetra-O-benzyl-1-O-(p-methoxybenzyl)-3-deoxy-3-azidomethyl-myo-inositol

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Chemical Property of (-)-2,4,5,6-tetra-O-benzyl-1-O-(p-methoxybenzyl)-3-deoxy-3-azidomethyl-myo-inositol

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Technology Process of (-)-2,4,5,6-tetra-O-benzyl-1-O-(p-methoxybenzyl)-3-deoxy-3-azidomethyl-myo-inositol

There total 4 articles about (-)-2,4,5,6-tetra-O-benzyl-1-O-(p-methoxybenzyl)-3-deoxy-3-azidomethyl-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: 80.0%

: 403651-37-6
(-)-2,4,5,6-tetra-O-benzyl-1-O-(p-methoxybenzyl)-3-deoxy-3-hydroxymethyl-myo-inositol

: 403651-42-3
(-)-2,4,5,6-tetra-O-benzyl-1-O-(p-methoxybenzyl)-3-deoxy-3-azidomethyl-myo-inositol

Guidance literature:: With Zn(N₃)2/bis-pyridine complex; triphenylphosphine; diethylazodicarboxylate; In toluene; at 80 ℃; for 4h;
DOI:10.1016/S0968-0896(01)00232-2

Reference yield:

: 141040-56-4
(+)-2,4,5,6-tetra-O-benzyl-1-O-(p-methoxybenzyl)-myo-inositol

: 403651-42-3
(-)-2,4,5,6-tetra-O-benzyl-1-O-(p-methoxybenzyl)-3-deoxy-3-azidomethyl-myo-inositol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 90 percent / Ac₂O / dimethylsulfoxide / 23 °C

2.1: potassium t-butoxide / toluene / 0.5 h / Heating

2.2: 80 percent / toluene / 2 h / 100 - 110 °C

3.1: 9-BBN / benzene; tetrahydrofuran / 20 °C

3.2: 71 percent / NaOH; H₂O₂ / benzene; tetrahydrofuran; methanol / 2 h / 55 °C

4.1: 80 percent / Zn(N₃)2*Py₂; Ph₃P; DEAD / toluene / 4 h / 80 °C

With 9-borabicyclo[3.3.1]nonane dimer; Zn(N₃)2/bis-pyridine complex; potassium tert-butylate; acetic anhydride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dimethyl sulfoxide; toluene; benzene; 2.2: Wittig reaction;
DOI:10.1016/S0968-0896(01)00232-2

Reference yield:

: 403651-35-4
(-)-2,4,5,6-tetra-O-benzyl-1-O-(p-methoxybenzyl)-3-deoxy-3-oxo-myo-inositol

: 403651-42-3
(-)-2,4,5,6-tetra-O-benzyl-1-O-(p-methoxybenzyl)-3-deoxy-3-azidomethyl-myo-inositol

Guidance literature:: Multi-step reaction with 3 steps

1.1: potassium t-butoxide / toluene / 0.5 h / Heating

1.2: 80 percent / toluene / 2 h / 100 - 110 °C

2.1: 9-BBN / benzene; tetrahydrofuran / 20 °C

2.2: 71 percent / NaOH; H₂O₂ / benzene; tetrahydrofuran; methanol / 2 h / 55 °C

3.1: 80 percent / Zn(N₃)2*Py₂; Ph₃P; DEAD / toluene / 4 h / 80 °C

With 9-borabicyclo[3.3.1]nonane dimer; Zn(N₃)2/bis-pyridine complex; potassium tert-butylate; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; toluene; benzene; 1.2: Wittig reaction;
DOI:10.1016/S0968-0896(01)00232-2