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

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Chemical Name:3-[(2S)-2-azido-3-hydroxypropyl]-1-(phenylsulfonyl)-2-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-1H-indole
CAS No.:252187-20-5
Molecular Formula:C₅₁H₅₀N₄O₈S
Molecular Weight:879.046
Hs Code.:

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

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Chemical Property of 3-[(2S)-2-azido-3-hydroxypropyl]-1-(phenylsulfonyl)-2-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-1H-indole

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Technology Process of 3-[(2S)-2-azido-3-hydroxypropyl]-1-(phenylsulfonyl)-2-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-1H-indole

There total 9 articles about 3-[(2S)-2-azido-3-hydroxypropyl]-1-(phenylsulfonyl)-2-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-1H-indole 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: 100.0%

: 252187-19-2
3-[(2S)-2-azido-3-[(tert-butyldimethylsilyl)oxy]propyl]-1-(phenylsulfonyl)-2-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-1H-indole

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

Guidance literature:: With toluene-4-sulfonic acid; In methanol; at 20 ℃; for 11h;
DOI:10.1002/chem.200390163

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 4 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

With n-butyllithium; potassium tert-butylate; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; hexane; N,N-dimethyl-formamide;
DOI:10.1002/chem.200390163

Reference yield:

: 98-09-9
benzenesulfonyl chloride

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

Guidance literature:: Multi-step reaction with 4 steps

1.1: BuLi / tetrahydrofuran; hexane / 1.25 h / -78 - 0 °C

1.2: 78 percent / tetrahydrofuran; hexane / 5 h / 20 °C

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

With n-butyllithium; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; hexane; N,N-dimethyl-formamide;
DOI:10.1002/chem.200390163