11-azidoundecyl O-(methyl 5-N,N-diacetylamino-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-2,6-di-O-benzyl-β-D-galactopyranoside

Base Information

Chemical Name:11-azidoundecyl O-(methyl 5-N,N-diacetylamino-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-2,6-di-O-benzyl-β-D-galactopyranoside
CAS No.:709041-02-1
Molecular Formula:C₅₃H₇₄N₄O₁₉
Molecular Weight:1071.19
Hs Code.:

11-azidoundecyl O-(methyl 5-N,N-diacetylamino-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-2,6-di-O-benzyl-β-D-galactopyranoside

Synonyms:11-azidoundecyl O-(methyl 5-N,N-diacetylamino-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-2,6-di-O-benzyl-β-D-galactopyranoside

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Chemical Property of 11-azidoundecyl O-(methyl 5-N,N-diacetylamino-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-2,6-di-O-benzyl-β-D-galactopyranoside

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Technology Process of 11-azidoundecyl O-(methyl 5-N,N-diacetylamino-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-2,6-di-O-benzyl-β-D-galactopyranoside

There total 8 articles about 11-azidoundecyl O-(methyl 5-N,N-diacetylamino-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-2,6-di-O-benzyl-β-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: 46.0%

: (4S,5R,6R)-4-Acetoxy-5-diacetylamino-2-ethylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

: 709040-82-4
11-azidoundecyl 2,6-di-O-benzyl-β-D-galactopyranoside

: 709041-02-1
11-azidoundecyl O-(methyl 5-N,N-diacetylamino-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-2,6-di-O-benzyl-β-D-galactopyranoside

Guidance literature:: (4S,5R,6R)-4-Acetoxy-5-diacetylamino-2-ethylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester; 11-azidoundecyl 2,6-di-O-benzyl-β-D-galactopyranoside; With 4 A molecular sieve; In acetonitrile; at -65 ℃; for 4h;

With N-iodo-succinimide; trifluorormethanesulfonic acid; In acetonitrile; for 1.5h; Further stages.;
DOI:10.1039/b400029c

Reference yield:

: 2592-58-7,3006-48-2,3006-49-3,13526-09-5,14679-57-3,22415-91-4,29884-70-6,41545-55-5,41545-56-6,41569-33-9,96996-90-6,121570-85-2,121570-86-3
1,2,3,4,6-Penta-O-benzoyl-α-D-galactopyranose

: 709041-02-1
11-azidoundecyl O-(methyl 5-N,N-diacetylamino-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-2,6-di-O-benzyl-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: HBr / acetic acid

1.2: 4 Angstroem molecular sieves / toluene / 1 h / -78 °C

1.3: silver triflate / toluene / 1 h / -78 - 10 °C

2.1: 12.0 g / NaOMe / methanol / 1 h / Heating

3.1: 96 percent / CSA / 3 h / Heating

4.1: NaH / dimethylformamide / 0.5 h

4.2: 90 percent / dimethylformamide / 2 h / 20 °C

5.1: 95 percent / aq. AcOH / 4 h / 85 °C

6.1: 4 Angstroem molecular sieves / acetonitrile; various solvent(s) / 4 h / -65 °C

6.2: 46 percent / NIS; TfOH / acetonitrile; various solvent(s) / 1.5 h

With 4 A molecular sieve; camphor-10-sulfonic acid; hydrogen bromide; sodium methylate; sodium hydride; acetic acid; In methanol; acetic acid; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1039/b400029c

Reference yield:

: 1611-56-9
1-Bromo-11-hydroxyundecane

: 709041-02-1
11-azidoundecyl O-(methyl 5-N,N-diacetylamino-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-2,6-di-O-benzyl-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1.1: 96 percent / NaN₃ / dimethylformamide / 50 h / 100 - 130 °C

2.1: HBr / acetic acid

2.2: 4 Angstroem molecular sieves / toluene / 1 h / -78 °C

2.3: silver triflate / toluene / 1 h / -78 - 10 °C

3.1: 12.0 g / NaOMe / methanol / 1 h / Heating

4.1: 96 percent / CSA / 3 h / Heating

5.1: NaH / dimethylformamide / 0.5 h

5.2: 90 percent / dimethylformamide / 2 h / 20 °C

6.1: 95 percent / aq. AcOH / 4 h / 85 °C

7.1: 4 Angstroem molecular sieves / acetonitrile; various solvent(s) / 4 h / -65 °C

7.2: 46 percent / NIS; TfOH / acetonitrile; various solvent(s) / 1.5 h

With sodium azide; 4 A molecular sieve; camphor-10-sulfonic acid; hydrogen bromide; sodium methylate; sodium hydride; acetic acid; In methanol; acetic acid; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1039/b400029c