α-azido-1-(phenylsulfonyl)-2-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-1H-indole-3-propanoic acid

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Chemical Name:α-azido-1-(phenylsulfonyl)-2-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-1H-indole-3-propanoic acid
CAS No.:252187-21-6
Molecular Formula:C₅₁H₄₈N₄O₉S
Molecular Weight:893.03
Hs Code.:

Synonyms:α-azido-1-(phenylsulfonyl)-2-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-1H-indole-3-propanoic acid

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Chemical Property of α-azido-1-(phenylsulfonyl)-2-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-1H-indole-3-propanoic acid

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Technology Process of α-azido-1-(phenylsulfonyl)-2-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-1H-indole-3-propanoic acid

There total 10 articles about α-azido-1-(phenylsulfonyl)-2-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-1H-indole-3-propanoic acid 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: 97.0%

: 252187-20-5
3-[(2S)-2-azido-3-hydroxypropyl]-1-(phenylsulfonyl)-2-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-1H-indole

: 252187-21-6
α-azido-1-(phenylsulfonyl)-2-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-1H-indole-3-propanoic acid

Guidance literature:: With 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene; In water; acetonitrile; at 20 ℃; for 3h;
DOI:10.1002/chem.200390163

Reference yield:

: 65827-59-0
2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl chloride

: 252187-21-6
α-azido-1-(phenylsulfonyl)-2-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-1H-indole-3-propanoic acid

Guidance literature:: Multi-step reaction with 5 steps

1.1: 94 percent / KO-t-Bu / tetrahydrofuran / 1 h / Heating

2.1: BuLi / tetrahydrofuran; hexane / 1.5 h / -78 °C

2.2: 63 percent / BF₃*OEt₂ / tetrahydrofuran; hexane / 20 h / -78 °C

3.1: 92 percent / NaH; nBu₄NI / dimethylformamide / 0 - 20 °C

4.1: 100 percent / TsOH*H₂O / methanol / 11 h / 20 °C

5.1: 97 percent / TEMPO; iodosobenzene diacetate / acetonitrile; H₂O / 3 h / 20 °C

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; n-butyllithium; [bis(acetoxy)iodo]benzene; potassium tert-butylate; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; hexane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1002/chem.200390163

Reference yield:

: 74372-90-0,112289-38-0,135202-48-1,148888-66-8,71696-32-7
1,2-anhydro-3,4,6-tri-O-benzyl-β-D-mannopyranose

: 252187-21-6
α-azido-1-(phenylsulfonyl)-2-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-1H-indole-3-propanoic acid

Guidance literature:: Multi-step reaction with 4 steps

1.1: BuLi / tetrahydrofuran; hexane / 1.5 h / -78 °C

1.2: 63 percent / BF₃*OEt₂ / tetrahydrofuran; hexane / 20 h / -78 °C

2.1: 92 percent / NaH; nBu₄NI / dimethylformamide / 0 - 20 °C

3.1: 100 percent / TsOH*H₂O / methanol / 11 h / 20 °C

4.1: 97 percent / TEMPO; iodosobenzene diacetate / acetonitrile; H₂O / 3 h / 20 °C

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; n-butyllithium; [bis(acetoxy)iodo]benzene; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; hexane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1002/chem.200390163