(2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1-6)-1-O-4-methoxybenzyl-2,3,4,5-tetra-O-benzyl-D-myo-inositol

Base Information

Chemical Name:(2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1-6)-1-O-4-methoxybenzyl-2,3,4,5-tetra-O-benzyl-D-myo-inositol
CAS No.:133076-44-5
Molecular Formula:C₆₉H₇₁N₃O₁₁
Molecular Weight:1118.34
Hs Code.:

Synonyms:(2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1-6)-1-O-4-methoxybenzyl-2,3,4,5-tetra-O-benzyl-D-myo-inositol

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Chemical Property of (2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1-6)-1-O-4-methoxybenzyl-2,3,4,5-tetra-O-benzyl-D-myo-inositol

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Technology Process of (2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1-6)-1-O-4-methoxybenzyl-2,3,4,5-tetra-O-benzyl-D-myo-inositol

There total 26 articles about (2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1-6)-1-O-4-methoxybenzyl-2,3,4,5-tetra-O-benzyl-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:

: 55682-48-9
1,6-anhydro-2-azido-3,4-di-O-benzyl-2-deoxy-D-glucopyranose

: 133076-44-5
(2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1-6)-1-O-4-methoxybenzyl-2,3,4,5-tetra-O-benzyl-D-myo-inositol

Guidance literature:: Multi-step reaction with 7 steps

1: 83 percent / 10percent CF₃COOH

2: 1. H₂NNH₂*HOAc 2. K₂CO₃ / 1. DMF 2. CH₂Cl₂

3: 84 percent / trimethylsilyl triflate, MS (4 Angstroem) / CH₂Cl₂ / -20 °C

4: 1. NaOMe 2. NaH, Bu₄NI / 1. MeOH/CH₂Cl₂ 2. DMF

5: 43 percent / HCl / methanol; CH₂Cl₂

6: 76 percent / Bu₂SnO, Bu₄NBr / toluene

7: NaH, Bu₄NI / dimethylformamide

With hydrogenchloride; trimethylsilyl trifluoromethanesulfonate; MS (4 Angstroem); tetrabutylammomium bromide; sodium methylate; hydrazinium monoacetate; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; potassium carbonate; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

Reference yield:

: 100-39-0
benzyl bromide

: (2R,3S,4R,5R,6R)-5-Azido-2-hydroxymethyl-6-[(1R,2S,3R,4R,5R,6R)-2,3,4,5-tetrakis-benzyloxy-6-(4-methoxy-benzyloxy)-cyclohexyloxy]-tetrahydro-pyran-3,4-diol

: 133076-44-5
(2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1-6)-1-O-4-methoxybenzyl-2,3,4,5-tetra-O-benzyl-D-myo-inositol

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃; for 3h; Inert atmosphere;
DOI:10.1039/c3ob42116c

Reference yield:

: 824-94-2
p-methoxybenzyl chloride

: 133076-44-5
(2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1-6)-1-O-4-methoxybenzyl-2,3,4,5-tetra-O-benzyl-D-myo-inositol

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) dibutyltin oxide, 2.) KI, CsF / 1.) MeOH, reflux, 2 h, 2.) DMF, RT, overnight

2: NaH / dimethylformamide / 1 h / Ambient temperature

With sodium hydride; di(n-butyl)tin oxide; cesium fluoride; potassium iodide; In N,N-dimethyl-formamide;
DOI:10.1016/0008-6215(95)00012-I