dibutyl 2-O-(2-(azidomethyl)benzoyl)-3,4,6-tri-O-benzyl-β-D-glucopyranosyl phosphate

Base Information

Chemical Name:dibutyl 2-O-(2-(azidomethyl)benzoyl)-3,4,6-tri-O-benzyl-β-D-glucopyranosyl phosphate
CAS No.:385422-02-6
Molecular Formula:C₄₃H₅₂N₃O₁₀P
Molecular Weight:801.874
Hs Code.:

Synonyms:dibutyl 2-O-(2-(azidomethyl)benzoyl)-3,4,6-tri-O-benzyl-β-D-glucopyranosyl phosphate

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Chemical Property of dibutyl 2-O-(2-(azidomethyl)benzoyl)-3,4,6-tri-O-benzyl-β-D-glucopyranosyl phosphate

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Technology Process of dibutyl 2-O-(2-(azidomethyl)benzoyl)-3,4,6-tri-O-benzyl-β-D-glucopyranosyl phosphate

There total 5 articles about dibutyl 2-O-(2-(azidomethyl)benzoyl)-3,4,6-tri-O-benzyl-β-D-glucopyranosyl phosphate 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: 71.0%

: 55628-54-1
3,4,6-tri-O-benzyl-D-glucal

: 107-66-4
dibutyl phosphate

: 289712-58-9
2-(azidomethyl)benzoyl chloride

: 385422-02-6
dibutyl 2-O-(2-(azidomethyl)benzoyl)-3,4,6-tri-O-benzyl-β-D-glucopyranosyl phosphate

Guidance literature:: 3,4,6-tri-O-benzyl-D-glucal; With 3,3-dimethyldioxirane; In dichloromethane; acetone; at 0 ℃; for 0.333333h;

dibutyl phosphate; In dichloromethane; at -78 ℃; for 0.25h;

2-(azidomethyl)benzoyl chloride; With dmap; In dichloromethane; at 0 ℃; for 0.166667h; Further stages.;
DOI:10.1021/jo015987h

Reference yield:

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

: 385422-02-6
dibutyl 2-O-(2-(azidomethyl)benzoyl)-3,4,6-tri-O-benzyl-β-D-glucopyranosyl phosphate

Guidance literature:: Multi-step reaction with 5 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 / 0.33 h / 0 °C

5.2: CH₂Cl₂ / 0.25 h / -78 °C

5.3: 71 percent / DMAP / CH₂Cl₂ / 0.17 h / 0 °C

With lithium hydroxide; N-Bromosuccinimide; thionyl chloride; sodium azide; 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

: 385422-02-6
dibutyl 2-O-(2-(azidomethyl)benzoyl)-3,4,6-tri-O-benzyl-β-D-glucopyranosyl phosphate

Guidance literature:: Multi-step reaction with 4 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 / 0.33 h / 0 °C

4.2: CH₂Cl₂ / 0.25 h / -78 °C

4.3: 71 percent / DMAP / CH₂Cl₂ / 0.17 h / 0 °C

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