allyl 4-O-(2'-azido-3',4',6'-tri-O-benzyl-2'-deoxy-β-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Base Information

Chemical Name:allyl 4-O-(2'-azido-3',4',6'-tri-O-benzyl-2'-deoxy-β-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
CAS No.:153804-92-3
Molecular Formula:C₅₈H₅₈N₄O₁₁
Molecular Weight:987.119
Hs Code.:

Synonyms:allyl 4-O-(2'-azido-3',4',6'-tri-O-benzyl-2'-deoxy-β-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

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Chemical Property of allyl 4-O-(2'-azido-3',4',6'-tri-O-benzyl-2'-deoxy-β-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

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Technology Process of allyl 4-O-(2'-azido-3',4',6'-tri-O-benzyl-2'-deoxy-β-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

There total 7 articles about allyl 4-O-(2'-azido-3',4',6'-tri-O-benzyl-2'-deoxy-β-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 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: 61.0%

: 89067-88-9
allyl-3,6-di-O-benzyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside

: 99049-62-4
2-azido-2-deoxy-3,4,6-tri-O-benzyl-α-D-glucopyranosyl trichloroacetimidate

: 153804-92-3
allyl 4-O-(2'-azido-3',4',6'-tri-O-benzyl-2'-deoxy-β-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at -20 ℃; for 2h;
DOI:10.1016/S0040-4039(00)61560-5

Reference yield:

: 10022-13-6
1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose

: 153804-92-3
allyl 4-O-(2'-azido-3',4',6'-tri-O-benzyl-2'-deoxy-β-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: 81 percent / trimethylsilyl triflate / CH₂Cl₂

2: 90 percent / conc. HCl / acetone / 70 °C

3: 95 percent / TsOH / dimethylformamide / 50 °C

4: 48 percent / CF₃SO₃H / CH₂Cl₂ / 2 h / 0 °C / pH 3

5: 93 percent / aq. AcOH / 1.5 h / 70 °C

6: 1.) (Bu₃Sn)2O, 2.) Bu₄NI / 1.) toluene, reflux, 4 h, 2.) 110 deg C, 5 h

7: 61 percent / MS₄A, BF₃*Et₂O / CH₂Cl₂ / 2 h / -20 °C

With hydrogenchloride; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; tetra-(n-butyl)ammonium iodide; toluene-4-sulfonic acid; acetic acid; bis(tri-n-butyltin)oxide; In dichloromethane; N,N-dimethyl-formamide; acetone;

Reference yield:

: 72333-26-7
allyl 3,4,6-tri-O-acetyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside

: 153804-92-3
allyl 4-O-(2'-azido-3',4',6'-tri-O-benzyl-2'-deoxy-β-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: 90 percent / conc. HCl / acetone / 70 °C

2: 95 percent / TsOH / dimethylformamide / 50 °C

3: 48 percent / CF₃SO₃H / CH₂Cl₂ / 2 h / 0 °C / pH 3

4: 93 percent / aq. AcOH / 1.5 h / 70 °C

5: 1.) (Bu₃Sn)2O, 2.) Bu₄NI / 1.) toluene, reflux, 4 h, 2.) 110 deg C, 5 h

6: 61 percent / MS₄A, BF₃*Et₂O / CH₂Cl₂ / 2 h / -20 °C

With hydrogenchloride; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; tetra-(n-butyl)ammonium iodide; toluene-4-sulfonic acid; acetic acid; bis(tri-n-butyltin)oxide; In dichloromethane; N,N-dimethyl-formamide; acetone;