Thexyldimethylsilyl 2-azido-6-O-benzyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-4-C-methylene-β-D-xylohex-4-ulopyranoside

Base Information

Chemical Name:Thexyldimethylsilyl 2-azido-6-O-benzyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-4-C-methylene-β-D-xylohex-4-ulopyranoside
CAS No.:174077-12-4
Molecular Formula:C₂₈H₄₉N₃O₄Si₂
Molecular Weight:547.886
Hs Code.:

Synonyms:Thexyldimethylsilyl 2-azido-6-O-benzyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-4-C-methylene-β-D-xylohex-4-ulopyranoside

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Chemical Property of Thexyldimethylsilyl 2-azido-6-O-benzyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-4-C-methylene-β-D-xylohex-4-ulopyranoside

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Technology Process of Thexyldimethylsilyl 2-azido-6-O-benzyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-4-C-methylene-β-D-xylohex-4-ulopyranoside

There total 5 articles about Thexyldimethylsilyl 2-azido-6-O-benzyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-4-C-methylene-β-D-xylohex-4-ulopyranoside 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: 76.0%

: 100-39-0
benzyl bromide

: Thexyldimethylsilyl 2-azido-3-O-(tert-butyldimethylsilyl)-2-deoxy-4-C-methylene-β-D-xylohex-4-ulopyranoside

: 174077-12-4
Thexyldimethylsilyl 2-azido-6-O-benzyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-4-C-methylene-β-D-xylohex-4-ulopyranoside

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h;

Reference yield:

: 157488-88-5
thexyldimethylsilyl 2-azido-2-deoxy-β-D-glucopyranoside

: 174077-12-4
Thexyldimethylsilyl 2-azido-6-O-benzyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-4-C-methylene-β-D-xylohex-4-ulopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: imidazole / dimethylformamide / 12 h / Ambient temperature

2: 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one / CH₂Cl₂ / 0.5 h / Ambient temperature

3: 45 percent / 1.6 N n-BuLi / tetrahydrofuran; diethyl ether / 1.) -40 deg C, 1 h, 2.) -40 deg C, 30 min; -5 deg C, 12 h

4: 95 percent / aq. AcOH / tetrahydrofuran / 24 h / 40 °C

5: 76 percent / NaH / dimethylformamide / 0.5 h / 0 °C

With 1H-imidazole; n-butyllithium; sodium hydride; Dess-Martin periodane; acetic acid; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

: 174077-09-9
Thexyldimethylsilyl 2-azido-3,6-di-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-glucopyranoside

: 174077-12-4
Thexyldimethylsilyl 2-azido-6-O-benzyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-4-C-methylene-β-D-xylohex-4-ulopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one / CH₂Cl₂ / 0.5 h / Ambient temperature

2: 45 percent / 1.6 N n-BuLi / tetrahydrofuran; diethyl ether / 1.) -40 deg C, 1 h, 2.) -40 deg C, 30 min; -5 deg C, 12 h

3: 95 percent / aq. AcOH / tetrahydrofuran / 24 h / 40 °C

4: 76 percent / NaH / dimethylformamide / 0.5 h / 0 °C

With n-butyllithium; sodium hydride; Dess-Martin periodane; acetic acid; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;