6-O-(3-azido-2-O-benzyl-3,6-dideoxy-α-D-glucopyranosyl)-1,3,2',6'-tetraazidoneamine

Base Information

Chemical Name:6-O-(3-azido-2-O-benzyl-3,6-dideoxy-α-D-glucopyranosyl)-1,3,2',6'-tetraazidoneamine
CAS No.:868258-70-2
Molecular Formula:C₂₅H₃₃N₁₅O₉
Molecular Weight:687.632
Hs Code.:

Synonyms:6-O-(3-azido-2-O-benzyl-3,6-dideoxy-α-D-glucopyranosyl)-1,3,2',6'-tetraazidoneamine

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Chemical Property of 6-O-(3-azido-2-O-benzyl-3,6-dideoxy-α-D-glucopyranosyl)-1,3,2',6'-tetraazidoneamine

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Technology Process of 6-O-(3-azido-2-O-benzyl-3,6-dideoxy-α-D-glucopyranosyl)-1,3,2',6'-tetraazidoneamine

There total 8 articles about 6-O-(3-azido-2-O-benzyl-3,6-dideoxy-α-D-glucopyranosyl)-1,3,2',6'-tetraazidoneamine 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:

: Benzoic acid (2R,3S,4S,5R,6R)-4-azido-5-benzyloxy-6-[(1S,2S,3R,4S,6R)-4,6-diazido-3-((2R,3R,4R,5R,6R)-4,5-diacetoxy-3-azido-6-azidomethyl-tetrahydro-pyran-2-yloxy)-2-hydroxy-cyclohexyloxy]-2-methyl-tetrahydro-pyran-3-yl ester

: 868258-70-2
6-O-(3-azido-2-O-benzyl-3,6-dideoxy-α-D-glucopyranosyl)-1,3,2',6'-tetraazidoneamine

Guidance literature:: With sodium methylate; In tetrahydrofuran; methanol; at 20 ℃; for 2h;
DOI:10.1021/jm050368c

Reference yield:

: 868258-60-0
phenyl 2-O-benzyl-1-thio-β-D-fucopyranoside

: 868258-70-2
6-O-(3-azido-2-O-benzyl-3,6-dideoxy-α-D-glucopyranosyl)-1,3,2',6'-tetraazidoneamine

Guidance literature:: Multi-step reaction with 8 steps

1.1: pyridine / CH₂Cl₂ / 0.5 h / 0 °C

2.1: CH₂Cl₂

3.1: 90 percent / MeONa / methanol / 2 h / 20 °C

4.1: 91 percent / DMAP; DIPEA / CH₂Cl₂ / -50 - -10 °C

5.1: CH₂Cl₂ / 1 h / 0 °C

6.1: 0.71 g / NaN₃ / CH₂Cl₂; dimethylformamide

7.1: N-iodosuccinimide / diethyl ether; CH₂Cl₂ / -70 - -40 °C

7.2: trifluoromethanesulfonic acid / diethyl ether; CH₂Cl₂ / 4 h

8.1: MeONa / tetrahydrofuran; methanol / 2 h / 20 °C

With pyridine; dmap; N-iodo-succinimide; sodium azide; sodium methylate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm050368c

Reference yield:

: 868258-62-2
phenyl 2-O-benzyl-6-deoxy-1-thio-β-D-allopyranoside

: 868258-70-2
6-O-(3-azido-2-O-benzyl-3,6-dideoxy-α-D-glucopyranosyl)-1,3,2',6'-tetraazidoneamine

Guidance literature:: Multi-step reaction with 5 steps

1.1: 91 percent / DMAP; DIPEA / CH₂Cl₂ / -50 - -10 °C

2.1: CH₂Cl₂ / 1 h / 0 °C

3.1: 0.71 g / NaN₃ / CH₂Cl₂; dimethylformamide

4.1: N-iodosuccinimide / diethyl ether; CH₂Cl₂ / -70 - -40 °C

4.2: trifluoromethanesulfonic acid / diethyl ether; CH₂Cl₂ / 4 h

5.1: MeONa / tetrahydrofuran; methanol / 2 h / 20 °C

With dmap; N-iodo-succinimide; sodium azide; sodium methylate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm050368c