6-azidohexyl (2,6-di-O-acetyl-β-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1->6)-2-deoxy-3,4-di-O-p-methylbenzoyl-2-phthalimido-β-D-glucopyranoside

Base Information

Chemical Name:6-azidohexyl (2,6-di-O-acetyl-β-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1->6)-2-deoxy-3,4-di-O-p-methylbenzoyl-2-phthalimido-β-D-glucopyranoside
CAS No.:651008-04-7
Molecular Formula:C₅₈H₆₈N₄O₂₄
Molecular Weight:1205.19
Hs Code.:

6-azidohexyl (2,6-di-O-acetyl-β-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1->6)-2-deoxy-3,4-di-O-p-methylbenzoyl-2-phthalimido-β-D-glucopyranoside

Synonyms:6-azidohexyl (2,6-di-O-acetyl-β-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1->6)-2-deoxy-3,4-di-O-p-methylbenzoyl-2-phthalimido-β-D-glucopyranoside

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Chemical Property of 6-azidohexyl (2,6-di-O-acetyl-β-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1->6)-2-deoxy-3,4-di-O-p-methylbenzoyl-2-phthalimido-β-D-glucopyranoside

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Technology Process of 6-azidohexyl (2,6-di-O-acetyl-β-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1->6)-2-deoxy-3,4-di-O-p-methylbenzoyl-2-phthalimido-β-D-glucopyranoside

There total 5 articles about 6-azidohexyl (2,6-di-O-acetyl-β-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1->6)-2-deoxy-3,4-di-O-p-methylbenzoyl-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: 84.0%

: 651008-03-6
6-azidohexyl (2,6-di-O-acetyl-3,4-di-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1->6)-2-deoxy-3,4-di-O-p-methylbenzoyl-2-phthalimido-β-D-glucopyranoside

: 651008-04-7
6-azidohexyl (2,6-di-O-acetyl-β-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1->6)-2-deoxy-3,4-di-O-p-methylbenzoyl-2-phthalimido-β-D-glucopyranoside

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 1.5h;
DOI:10.1016/S0008-6215(03)00313-6

Reference yield:

: 87190-67-8
3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-O-trichloroacetimidate

: 651008-04-7
6-azidohexyl (2,6-di-O-acetyl-β-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1->6)-2-deoxy-3,4-di-O-p-methylbenzoyl-2-phthalimido-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: 89 percent / BF₃*Et₂O / CH₂Cl₂ / 3 h / 0 °C

2: 100 percent / NaOMe / methanol; CH₂Cl₂ / 5 h / pH 8

3: 88 percent / pyridine; 4-dimethylaminopyridine; Et₃N / CH₂Cl₂ / 16 h

4: 69 percent / pyridine; CH₂Cl₂ / 20 h / 0 °C

5: 75 percent / acetyl chloride / toluene; methanol / 4 h / 0 °C

6: 62 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 0.33 h / 0 - 20 °C

7: 84 percent / aq. TFA / CH₂Cl₂ / 1.5 h / 0 °C

With pyridine; dmap; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; sodium methylate; triethylamine; acetyl chloride; trifluoroacetic acid; In pyridine; methanol; dichloromethane; toluene;
DOI:10.1016/S0008-6215(03)00313-6

Reference yield:

: 651007-98-6
6-azidohexyl 2-deoxy-3,4-di-O-p-methylbenzoyl-2-phthalimido-β-D-glucopyranoside

: 651008-04-7
6-azidohexyl (2,6-di-O-acetyl-β-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1->6)-2-deoxy-3,4-di-O-p-methylbenzoyl-2-phthalimido-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: 62 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 0.33 h / 0 - 20 °C

2: 84 percent / aq. TFA / CH₂Cl₂ / 1.5 h / 0 °C

With trimethylsilyl trifluoromethanesulfonate; trifluoroacetic acid; In dichloromethane;
DOI:10.1016/S0008-6215(03)00313-6