methyl 6-O-(2-(azidomethyl)benzoyl)-3,4-di-O-benzyl-2-levulinyl-β-D-glucopyranoside

Base Information

Chemical Name:methyl 6-O-(2-(azidomethyl)benzoyl)-3,4-di-O-benzyl-2-levulinyl-β-D-glucopyranoside
CAS No.:385421-93-2
Molecular Formula:C₃₄H₃₇N₃O₉
Molecular Weight:631.682
Hs Code.:

Synonyms:methyl 6-O-(2-(azidomethyl)benzoyl)-3,4-di-O-benzyl-2-levulinyl-β-D-glucopyranoside

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Chemical Property of methyl 6-O-(2-(azidomethyl)benzoyl)-3,4-di-O-benzyl-2-levulinyl-β-D-glucopyranoside

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Technology Process of methyl 6-O-(2-(azidomethyl)benzoyl)-3,4-di-O-benzyl-2-levulinyl-β-D-glucopyranoside

There total 10 articles about methyl 6-O-(2-(azidomethyl)benzoyl)-3,4-di-O-benzyl-2-levulinyl-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: 93.0%

: 123-76-2
levulinic acid

: 373606-22-5
methyl 6-O-(2-(azidomethyl)benzoyl)-3,4-di-O-benzyl-β-D-glucopyranoside

: 385421-93-2
methyl 6-O-(2-(azidomethyl)benzoyl)-3,4-di-O-benzyl-2-levulinyl-β-D-glucopyranoside

Guidance literature:: levulinic acid; With dmap; bis-2-propyl carbonate; In dichloromethane; at 0 ℃;

methyl 6-O-(2-(azidomethyl)benzoyl)-3,4-di-O-benzyl-β-D-glucopyranoside; In dichloromethane; at 20 ℃; for 8h; Further stages.;
DOI:10.1021/jo015987h

Reference yield:

: 2417-73-4
methyl 2-bromomethylbenzoate

: 385421-93-2
methyl 6-O-(2-(azidomethyl)benzoyl)-3,4-di-O-benzyl-2-levulinyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 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: 91 percent / DMAP / CH₂Cl₂ / 0.17 h / 20 °C

5.1: 85 percent / NaOAc / PdCl₂ / acetic acid; H₂O / 3 h / 70 °C

6.1: DIPC; DMAP / CH₂Cl₂ / 0 °C

6.2: 93 percent / CH₂Cl₂ / 8 h / 20 °C

With dmap; lithium hydroxide; thionyl chloride; sodium azide; bis-2-propyl carbonate; water; sodium acetate; palladium dichloride; In tetrahydrofuran; ethanol; dichloromethane; chloroform; water; acetic acid;
DOI:10.1021/jo015987h

Reference yield:

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

: 385421-93-2
methyl 6-O-(2-(azidomethyl)benzoyl)-3,4-di-O-benzyl-2-levulinyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 7 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: 91 percent / DMAP / CH₂Cl₂ / 0.17 h / 20 °C

6.1: 85 percent / NaOAc / PdCl₂ / acetic acid; H₂O / 3 h / 70 °C

7.1: DIPC; DMAP / CH₂Cl₂ / 0 °C

7.2: 93 percent / CH₂Cl₂ / 8 h / 20 °C

With dmap; lithium hydroxide; N-Bromosuccinimide; thionyl chloride; sodium azide; bis-2-propyl carbonate; water; sodium acetate; palladium dichloride; dibenzoyl peroxide; In tetrahydrofuran; tetrachloromethane; ethanol; dichloromethane; chloroform; water; acetic acid;
DOI:10.1021/jo015987h