O-(2-O-benzoyl-3-O-benzyl-6-deoxy-β-D-xylo-hex-5-enopyranosyl)-(1->4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose

Base Information

Chemical Name:O-(2-O-benzoyl-3-O-benzyl-6-deoxy-β-D-xylo-hex-5-enopyranosyl)-(1->4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose
CAS No.:104139-74-4
Molecular Formula:C₃₃H₃₃N₃O₉
Molecular Weight:615.64
Hs Code.:

Synonyms:O-(2-O-benzoyl-3-O-benzyl-6-deoxy-β-D-xylo-hex-5-enopyranosyl)-(1->4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose

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Chemical Property of O-(2-O-benzoyl-3-O-benzyl-6-deoxy-β-D-xylo-hex-5-enopyranosyl)-(1->4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose

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Technology Process of O-(2-O-benzoyl-3-O-benzyl-6-deoxy-β-D-xylo-hex-5-enopyranosyl)-(1->4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose

There total 13 articles about O-(2-O-benzoyl-3-O-benzyl-6-deoxy-β-D-xylo-hex-5-enopyranosyl)-(1->4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose 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: 88.1%

: 104139-73-3
O-(2-O-benzoyl-3-O-benzyl-6-deoxy-6-iodo-β-D-glucopyranosyl)-(1->4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose

: 104139-74-4
O-(2-O-benzoyl-3-O-benzyl-6-deoxy-β-D-xylo-hex-5-enopyranosyl)-(1->4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; for 18h; Heating;
DOI:10.1016/S0008-6215(00)90842-5

Reference yield:

: 97390-18-6
1,6-anhydro-4-O-(4,6-O-benzylidene-β-D-glucopyranosyl)-2,3-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-glucopyranose

: 104139-74-4
O-(2-O-benzoyl-3-O-benzyl-6-deoxy-β-D-xylo-hex-5-enopyranosyl)-(1->4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose

Guidance literature:: Multi-step reaction with 11 steps

1: 1.) dibutyltin oxide; 2.) tetrabutylammonium iodide / 1.) toluene, 15 h, reflux; 2.) 5 h, 100 deg C

2: 98 percent / pyridine / 5 h / Ambient temperature

3: 88 percent / 1 M tetrabutylammonium fluoride / acetonitrile; H₂O; tetrahydrofuran / 10 h / Ambient temperature

4: 91.5 percent / CHCl₃; pyridine / 96 h / Ambient temperature

5: 94.6 percent / 60 percent NaH / tetrahydrofuran; dimethylformamide; paraffin / 0.08 h / Ambient temperature

6: 88.5 percent / sodium azide, ammonium chloride / dimethylformamide; H₂O / 40 h / 110 °C

7: 91.4 percent / 60 percent NaH, tetrabutylammonium iodide / paraffin; tetrahydrofuran / 0.83 h / Ambient temperature

8: 85.6 percent / cupric chloride dihydrate / tetrahydrofuran; ethanol / 1.5 h / Heating

9: 1.) bis(tributyltin)oxide / 1.) toluene, 3 h, reflux; 2.) 3 h, 80 deg C

10: 95.9 percent / NaI / acetone / 14 h / Heating

11: 88.1 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / tetrahydrofuran / 18 h / Heating

With pyridine; sodium azide; ammonium chloride; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; bis(tri-n-butyltin)oxide; sodium iodide; copper dichloride; In tetrahydrofuran; pyridine; ethanol; chloroform; water; N,N-dimethyl-formamide; acetone; acetonitrile; paraffin;
DOI:10.1016/S0008-6215(00)90842-5

Reference yield:

: 115997-40-5
O-(2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-1,6:2,3-dianhydro-β-D-mannopyranose

: 104139-74-4
O-(2-O-benzoyl-3-O-benzyl-6-deoxy-β-D-xylo-hex-5-enopyranosyl)-(1->4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose

Guidance literature:: Multi-step reaction with 6 steps

1: 88.5 percent / sodium azide, ammonium chloride / dimethylformamide; H₂O / 40 h / 110 °C

2: 91.4 percent / 60 percent NaH, tetrabutylammonium iodide / paraffin; tetrahydrofuran / 0.83 h / Ambient temperature

3: 85.6 percent / cupric chloride dihydrate / tetrahydrofuran; ethanol / 1.5 h / Heating

4: 1.) bis(tributyltin)oxide / 1.) toluene, 3 h, reflux; 2.) 3 h, 80 deg C

5: 95.9 percent / NaI / acetone / 14 h / Heating

6: 88.1 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / tetrahydrofuran / 18 h / Heating

With sodium azide; ammonium chloride; tetra-(n-butyl)ammonium iodide; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; bis(tri-n-butyltin)oxide; sodium iodide; copper dichloride; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide; acetone; paraffin;
DOI:10.1016/S0008-6215(00)90842-5