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

Base Information

Chemical Name:3-[(2S)-2-azido-3-[(tert-butyldimethylsilyl)oxy]propyl]-1-(phenylsulfonyl)-2-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-1H-indole
CAS No.:252187-18-1
Molecular Formula:C₅₀H₅₈N₄O₈SSi
Molecular Weight:903.184
Hs Code.:

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

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Chemical Property of 3-[(2S)-2-azido-3-[(tert-butyldimethylsilyl)oxy]propyl]-1-(phenylsulfonyl)-2-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-1H-indole

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Technology Process of 3-[(2S)-2-azido-3-[(tert-butyldimethylsilyl)oxy]propyl]-1-(phenylsulfonyl)-2-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-1H-indole

There total 6 articles about 3-[(2S)-2-azido-3-[(tert-butyldimethylsilyl)oxy]propyl]-1-(phenylsulfonyl)-2-(3,4,6-tri-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: 63.0%

: 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

: 252187-17-0
3-[(2S)-2-azido-3-[(tert-butyldimethylsilyl)oxy]propyl]-1-(phenylsulfonyl)-1H-indole

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

: 252187-18-1
3-[(2S)-2-azido-3-[(tert-butyldimethylsilyl)oxy]propyl]-1-(phenylsulfonyl)-2-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-1H-indole

Guidance literature:: 3-[(2S)-2-azido-3-[(tert-butyldimethylsilyl)oxy]propyl]-1-(phenylsulfonyl)-1H-indole; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1.5h;

1,2-anhydro-3,4,6-tri-O-benzyl-β-D-mannopyranose; With boron trifluoride diethyl etherate; In tetrahydrofuran; hexane; at -78 ℃; for 20h;
DOI:10.1002/chem.200390163

Reference yield:

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

: 252187-18-1
3-[(2S)-2-azido-3-[(tert-butyldimethylsilyl)oxy]propyl]-1-(phenylsulfonyl)-2-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-1H-indole

Guidance literature:: Multi-step reaction with 2 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

With n-butyllithium; potassium tert-butylate; In tetrahydrofuran; hexane;
DOI:10.1002/chem.200390163

Reference yield:

: 98-09-9
benzenesulfonyl chloride

: 252187-18-1
3-[(2S)-2-azido-3-[(tert-butyldimethylsilyl)oxy]propyl]-1-(phenylsulfonyl)-2-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-1H-indole

Guidance literature:: Multi-step reaction with 2 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

With n-butyllithium; In tetrahydrofuran; hexane;
DOI:10.1002/chem.200390163