n-pentenyl 2-O-(2-(azidomethyl)benzoyl)-3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->4)-3-O-benzoyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Base Information

Chemical Name:n-pentenyl 2-O-(2-(azidomethyl)benzoyl)-3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->4)-3-O-benzoyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
CAS No.:385422-10-6
Molecular Formula:C₆₈H₆₆N₄O₁₄
Molecular Weight:1163.29
Hs Code.:

n-pentenyl 2-O-(2-(azidomethyl)benzoyl)-3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->4)-3-O-benzoyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Synonyms:n-pentenyl 2-O-(2-(azidomethyl)benzoyl)-3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->4)-3-O-benzoyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

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Chemical Property of n-pentenyl 2-O-(2-(azidomethyl)benzoyl)-3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->4)-3-O-benzoyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

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Technology Process of n-pentenyl 2-O-(2-(azidomethyl)benzoyl)-3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->4)-3-O-benzoyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

There total 9 articles about n-pentenyl 2-O-(2-(azidomethyl)benzoyl)-3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->4)-3-O-benzoyl-6-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: 96.0%

: 385422-09-3
n-pentenyl 3-O-benzoyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

: 385422-08-2
dibutyl 2-O-(2-(azidomethyl)benzoyl)-3,4,6-tri-O-benzyl-β-D-galactopyranosyl phosphate

: 385422-10-6
n-pentenyl 2-O-(2-(azidomethyl)benzoyl)-3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->4)-3-O-benzoyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -60 - -50 ℃; for 0.166667h;
DOI:10.1021/jo015987h

Reference yield:

: 89-71-4
2-Methyl-benzoic acid methyl ester

: 385422-10-6
n-pentenyl 2-O-(2-(azidomethyl)benzoyl)-3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->4)-3-O-benzoyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: NBS / benzoyl peroxide / CCl₄ / 24 h / Heating

2.1: 4.58 g / NaN₃ / ethanol / 48 h / 20 °C

3.1: 97 percent / LiOH*H₂O; H₂O / tetrahydrofuran / 60 h / 20 °C

4.1: 97 percent / thionyl chloride / CHCl₃ / 5 h / Heating

5.1: dimethyl dioxirane / CH₂Cl₂; acetone / 0.25 h / 0 °C

5.2: CH₂Cl₂ / 0.33 h / -78 - 0 °C

5.3: 62 percent / DMAP / CH₂Cl₂ / 3 h / 20 °C

6.1: 96 percent / TMSOTf / CH₂Cl₂ / 0.17 h / -60 - -50 °C

With lithium hydroxide; N-Bromosuccinimide; thionyl chloride; sodium azide; trimethylsilyl trifluoromethanesulfonate; water; 3,3-dimethyldioxirane; dibenzoyl peroxide; In tetrahydrofuran; tetrachloromethane; ethanol; dichloromethane; chloroform; acetone;
DOI:10.1021/jo015987h

Reference yield:

: 2417-73-4
methyl 2-bromomethylbenzoate

: 385422-10-6
n-pentenyl 2-O-(2-(azidomethyl)benzoyl)-3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->4)-3-O-benzoyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: 4.58 g / NaN₃ / ethanol / 48 h / 20 °C

2.1: 97 percent / LiOH*H₂O; H₂O / tetrahydrofuran / 60 h / 20 °C

3.1: 97 percent / thionyl chloride / CHCl₃ / 5 h / Heating

4.1: dimethyl dioxirane / CH₂Cl₂; acetone / 0.25 h / 0 °C

4.2: CH₂Cl₂ / 0.33 h / -78 - 0 °C

4.3: 62 percent / DMAP / CH₂Cl₂ / 3 h / 20 °C

5.1: 96 percent / TMSOTf / CH₂Cl₂ / 0.17 h / -60 - -50 °C

With lithium hydroxide; thionyl chloride; sodium azide; trimethylsilyl trifluoromethanesulfonate; water; 3,3-dimethyldioxirane; In tetrahydrofuran; ethanol; dichloromethane; chloroform; acetone;
DOI:10.1021/jo015987h