(2-azido-3,6-di-O-benzyl-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: (2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->6)-2,3,4,5-tetra-O-benzyl-1-O-(4-methoxybenzyl)-D-myo-inositol
• CAS No.: 220734-77-0
• Molecular Formula: C₆₂H₆₅N₃O₁₁
• Molecular Weight: 1028.21
• Mol file: 220734-77-0.mol

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

Chemical Property of (2-azido-3,6-di-O-benzyl-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:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 14 articles about (2-azido-3,6-di-O-benzyl-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: 87.0%

(2-azido-3-O-benzyl-4,6-di-O-benzylidene-2-deoxy-α-D-glucopyranosyl)-(1->6)-2,3,4,5-tetra-O-benzyl-1-O-(4-methoxybenzyl)-D-myo-inositol (380366-32-5) → (2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->6)-2,3,4,5-tetra-O-benzyl-1-O-(4-methoxybenzyl)-D-myo-inositol (220734-77-0)

Guidance literature:

With hydrochloric acid diethyl ether; sodium cyanoborohydride; In tetrahydrofuran; at 20 ℃; for 3h; pH=1;

DOI:10.1021/jo015840q

Reference yield: 57.0%

(+)-1D-2,3,4,5-tetra-O-benzyl-1-O-(4-methoxybenzyl)-myo-inositol (129261-63-8) + 4-O-allyl-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside trichloroacetimidate (717902-61-9) → (2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->6)-2,3,4,5-tetra-O-benzyl-1-O-(4-methoxybenzyl)-D-myo-inositol (220734-77-0)

Guidance literature:

(+)-1D-2,3,4,5-tetra-O-benzyl-1-O-(4-methoxybenzyl)-myo-inositol; 4-O-allyl-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside trichloroacetimidate; With trimethylsilyl trifluoromethanesulfonate; In 1,4-dioxane; toluene; at 0 ℃; for 0.25h; Molecular sieve; Inert atmosphere;

With (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; hydrogen; In tetrahydrofuran; at 20 ℃; for 0.5h;

With mercury dichloride; mercury(II) oxide; In water; acetone; for 0.166667h;

DOI:10.1039/c7cc03056h

Reference yield:

1-D-6-O-allyl-2,3,4,5-tetra-O-benzyl-1-O-(4-methoxybenzyl)-myo-inositol (154459-82-2) → (2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->6)-2,3,4,5-tetra-O-benzyl-1-O-(4-methoxybenzyl)-D-myo-inositol (220734-77-0)

Guidance literature:

Multi-step reaction with 6 steps

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

1.2: 95 percent / 1N HCl / acetone / 0.17 h / Heating

2.1: 70 percent / 4 Angstroem MS; TMSOTf / CH₂Cl₂ / 0.33 h / 0 °C

3.1: Na / methanol; diethyl ether / 2 h / 20 °C

4.1: CSA / acetonitrile / 2.5 h / 20 °C

5.1: 2.56 g / NaH / dimethylformamide / 0 - 20 °C

6.1: 87 percent / NaBH₃CN; HCl*OEt₂ / tetrahydrofuran / 3 h / 20 °C / pH 1

With trimethylsilyl trifluoromethanesulfonate; 4 Angstroem MS; camphor-10-sulfonic acid; sodium; hydrochloric acid diethyl ether; sodium hydride; sodium cyanoborohydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; Wilkinson's catalyst; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo015840q

upstream raw materials:

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

3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl trichloroacetimidate

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

p-methoxybenzyl chloride

Downstream raw materials:

2-azido-3,6-dibenzyl-2-deoxy-4-phenoxyacetyl-α-D-glucopyranosyl-(1->6)-2,3,4,5-tetrabenzyl-1-(4-methoxybenzyl)-myo-inositol

2-azido-3,6-dibenzyl-2-deoxy-4-phenoxyacetyl-α-D-glucopyranosyl-(1->6)-2,3,4,5-tetrabenzyl-myo-inositol

Benzoic acid (1R,2R,3R,4R,5S,6R)-2,3,4,5-tetrakis-benzyloxy-6-((2R,3R,4R,5S,6R)-4-benzyloxy-6-benzyloxymethyl-3-tert-butoxycarbonylamino-5-hydroxy-tetrahydro-pyran-2-yloxy)-cyclohexyl ester

2-azido-3,6-dibenzyl-2-deoxy-4-phenoxyacetyl-α-D-glucopyranosyl-(1->6)-1-benzoyl-2,3,4,5-tetrabenzyl-myo-inositol