2-O-(2-(azidomethyl)benzoyl)-3,4,6-tri-O-benzyl-β-D-glucopyranosyl-(1->6)-1,2:3,4-diisopropylidene-α-D-galactopyranoside

Base Information

Chemical Name:2-O-(2-(azidomethyl)benzoyl)-3,4,6-tri-O-benzyl-β-D-glucopyranosyl-(1->6)-1,2:3,4-diisopropylidene-α-D-galactopyranoside
CAS No.:385422-03-7
Molecular Formula:C₄₇H₅₃N₃O₁₂
Molecular Weight:851.951
Hs Code.:

Synonyms:2-O-(2-(azidomethyl)benzoyl)-3,4,6-tri-O-benzyl-β-D-glucopyranosyl-(1->6)-1,2:3,4-diisopropylidene-α-D-galactopyranoside

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Chemical Property of 2-O-(2-(azidomethyl)benzoyl)-3,4,6-tri-O-benzyl-β-D-glucopyranosyl-(1->6)-1,2:3,4-diisopropylidene-α-D-galactopyranoside

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Technology Process of 2-O-(2-(azidomethyl)benzoyl)-3,4,6-tri-O-benzyl-β-D-glucopyranosyl-(1->6)-1,2:3,4-diisopropylidene-α-D-galactopyranoside

There total 7 articles about 2-O-(2-(azidomethyl)benzoyl)-3,4,6-tri-O-benzyl-β-D-glucopyranosyl-(1->6)-1,2:3,4-diisopropylidene-α-D-galactopyranoside 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: 94.0%

: 4064-06-6
1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

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

: 385422-03-7
2-O-(2-(azidomethyl)benzoyl)-3,4,6-tri-O-benzyl-β-D-glucopyranosyl-(1->6)-1,2:3,4-diisopropylidene-α-D-galactopyranoside

Guidance literature:: With t-butyldimethylsiyl triflate; In dichloromethane; at -78 ℃; for 0.166667h;
DOI:10.1021/jo015987h

Reference yield: 88.0%

: 4064-06-6
1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

: 385422-04-8
thioethyl 2-O-(2-(azidomethyl)benzoyl)-3,4,6-tri-O-benzyl-β-D-glucopyranoside

: 385422-03-7
2-O-(2-(azidomethyl)benzoyl)-3,4,6-tri-O-benzyl-β-D-glucopyranosyl-(1->6)-1,2:3,4-diisopropylidene-α-D-galactopyranoside

Guidance literature:: With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; In dichloromethane; at 0 ℃; for 0.166667h;
DOI:10.1021/jo015987h

Reference yield:

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

: 385422-03-7
2-O-(2-(azidomethyl)benzoyl)-3,4,6-tri-O-benzyl-β-D-glucopyranosyl-(1->6)-1,2:3,4-diisopropylidene-α-D-galactopyranoside

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 / 0.33 h / 0 °C

5.2: CH₂Cl₂ / 0.25 h / -78 °C

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

6.1: 94 percent / TBSOTf / CH₂Cl₂ / 0.17 h / -78 °C

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