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

Base Information

Chemical Name:(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->6)-2,3,4,5-tetra-O-benzyl-1-O-(4-methoxybenzyl)-D-myo-inositol
CAS No.:380366-31-4
Molecular Formula:C₅₄H₅₉N₃O₁₄
Molecular Weight:974.074
Hs Code.:

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

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Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

Safty Information:

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

There total 13 articles about (3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->6)-2,3,4,5-tetra-O-benzyl-1-O-(4-methoxybenzyl)-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: 90.0%

: 129261-63-8
(+)-1D-2,3,4,5-tetra-O-benzyl-1-O-(4-methoxybenzyl)-myo-inositol

: 145840-43-3
3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-glucopyranosyl trichloroacetimidate

: 380366-31-4
(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->6)-2,3,4,5-tetra-O-benzyl-1-O-(4-methoxybenzyl)-D-myo-inositol

Guidance literature:: (+)-1D-2,3,4,5-tetra-O-benzyl-1-O-(4-methoxybenzyl)-myo-inositol; 3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-glucopyranosyl trichloroacetimidate; In dichloromethane; at 20 ℃; for 0.5h; Ionic liquid; Molecular sieve;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 ℃; Inert atmosphere; Molecular sieve;
DOI:10.1039/c3ob42116c

Reference yield: 70.0%

: 94715-56-7
3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl trichloroacetimidate

: 129261-63-8
(+)-1D-2,3,4,5-tetra-O-benzyl-1-O-(4-methoxybenzyl)-myo-inositol

: 380366-31-4
(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->6)-2,3,4,5-tetra-O-benzyl-1-O-(4-methoxybenzyl)-D-myo-inositol

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; 4 Angstroem MS; In dichloromethane; at 0 ℃; for 0.333333h;
DOI:10.1021/jo015840q

Reference yield:

: 824-94-2
p-methoxybenzyl chloride

: 380366-31-4
(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->6)-2,3,4,5-tetra-O-benzyl-1-O-(4-methoxybenzyl)-D-myo-inositol

Guidance literature:: Multi-step reaction with 5 steps

1.1: NaH / dimethylformamide / 3 h / 0 °C

2.1: 3.0 g / CSA / methanol / 8 h / 20 °C

3.1: 92 percent / NaH / dimethylformamide / 2 h / 20 °C

4.1: DBU / (PPh₃)3RhCl / ethanol / 1 h / Heating

4.2: 95 percent / 1N HCl / acetone / 0.17 h / Heating

5.1: 70 percent / 4 Angstroem MS; TMSOTf / CH₂Cl₂ / 0.33 h / 0 °C

With trimethylsilyl trifluoromethanesulfonate; 4 Angstroem MS; camphor-10-sulfonic acid; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; Wilkinson's catalyst; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo015840q