5-azido-6-O-tert-butyldiphenylsilyl-3,5-dideoxy-3-fluoro-1,2-O-isopropylidene-α-D-glucofuranose

Base Information

Chemical Name:5-azido-6-O-tert-butyldiphenylsilyl-3,5-dideoxy-3-fluoro-1,2-O-isopropylidene-α-D-glucofuranose
CAS No.:141242-35-5
Molecular Formula:C₂₅H₃₂FN₃O₄Si
Molecular Weight:485.631
Hs Code.:

Synonyms:5-azido-6-O-tert-butyldiphenylsilyl-3,5-dideoxy-3-fluoro-1,2-O-isopropylidene-α-D-glucofuranose

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Chemical Property of 5-azido-6-O-tert-butyldiphenylsilyl-3,5-dideoxy-3-fluoro-1,2-O-isopropylidene-α-D-glucofuranose

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Technology Process of 5-azido-6-O-tert-butyldiphenylsilyl-3,5-dideoxy-3-fluoro-1,2-O-isopropylidene-α-D-glucofuranose

There total 8 articles about 5-azido-6-O-tert-butyldiphenylsilyl-3,5-dideoxy-3-fluoro-1,2-O-isopropylidene-α-D-glucofuranose 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:

: 110920-92-8
(3aR,5R,6S,6aR)-5-((R)-2-(tert-butyldiphenylsilyloxy)-1-hydroxyethyl)-2,2-dimethyltetrahydrofuro(3,2-d)(1,3)dioxol-6-ol

: 141242-35-5
5-azido-6-O-tert-butyldiphenylsilyl-3,5-dideoxy-3-fluoro-1,2-O-isopropylidene-α-D-glucofuranose

Guidance literature:: Multi-step reaction with 6 steps

1: 94.4 percent / fused zinc chloride / 22 h / Ambient temperature

2: 74.1 percent / N-bromosuccinimide, barium carbonate / CCl₄ / 4 h / Heating

3: 65.5 percent / methanolic 1M sodium methoxide / 4 h / Ambient temperature

4: 1) phosphorus pentaoxide, 2) sodium borohydride / 1) DMF, methyl sulphoxide, 65-70 deg C, 3.5 h, 2) MeOH, 10 min at 0 deg C and 45 min at r.t.

5: 71.9 percent / sodium azide / dimethylformamide / 17 h / 90 °C

6: 1) triflic anhydride, pyridine, 2) tris(dimethylamino)sulphonium difluorotrimethylsilicate / 1) CH₂Cl₂, -5 deg C, 1 h, 2) CH₂Cl₂, -3 deg C, 1 h

With pyridine; phosphorus pentaoxide; sodium tetrahydroborate; N-Bromosuccinimide; sodium azide; trifluoromethylsulfonic anhydride; tris(dimethylamino)sulfonium trimethylsilyldifluoride; sodium methylate; barium carbonate; zinc(II) chloride; In tetrachloromethane; N,N-dimethyl-formamide;
DOI:10.1016/0008-6215(92)80042-Y

Reference yield:

: 110920-93-9
3,5-O-benzylidene-6-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-α-D-glucofuranose

: 141242-35-5
5-azido-6-O-tert-butyldiphenylsilyl-3,5-dideoxy-3-fluoro-1,2-O-isopropylidene-α-D-glucofuranose

Guidance literature:: Multi-step reaction with 5 steps

1: 74.1 percent / N-bromosuccinimide, barium carbonate / CCl₄ / 4 h / Heating

2: 65.5 percent / methanolic 1M sodium methoxide / 4 h / Ambient temperature

3: 1) phosphorus pentaoxide, 2) sodium borohydride / 1) DMF, methyl sulphoxide, 65-70 deg C, 3.5 h, 2) MeOH, 10 min at 0 deg C and 45 min at r.t.

4: 71.9 percent / sodium azide / dimethylformamide / 17 h / 90 °C

5: 1) triflic anhydride, pyridine, 2) tris(dimethylamino)sulphonium difluorotrimethylsilicate / 1) CH₂Cl₂, -5 deg C, 1 h, 2) CH₂Cl₂, -3 deg C, 1 h

With pyridine; phosphorus pentaoxide; sodium tetrahydroborate; N-Bromosuccinimide; sodium azide; trifluoromethylsulfonic anhydride; tris(dimethylamino)sulfonium trimethylsilyldifluoride; sodium methylate; barium carbonate; In tetrachloromethane; N,N-dimethyl-formamide;
DOI:10.1016/0008-6215(92)80042-Y

Reference yield:

: 141242-27-5
5-bromo-6-O-tert-butyldiphenylsilyl-5-deoxy-1,2-O-isopropylidene-β-L-idofuranose

: 141242-35-5
5-azido-6-O-tert-butyldiphenylsilyl-3,5-dideoxy-3-fluoro-1,2-O-isopropylidene-α-D-glucofuranose

Guidance literature:: Multi-step reaction with 3 steps

1: 1) phosphorus pentaoxide, 2) sodium borohydride / 1) DMF, methyl sulphoxide, 65-70 deg C, 3.5 h, 2) MeOH, 10 min at 0 deg C and 45 min at r.t.

2: 71.9 percent / sodium azide / dimethylformamide / 17 h / 90 °C

3: 1) triflic anhydride, pyridine, 2) tris(dimethylamino)sulphonium difluorotrimethylsilicate / 1) CH₂Cl₂, -5 deg C, 1 h, 2) CH₂Cl₂, -3 deg C, 1 h

With pyridine; phosphorus pentaoxide; sodium tetrahydroborate; sodium azide; trifluoromethylsulfonic anhydride; tris(dimethylamino)sulfonium trimethylsilyldifluoride; In N,N-dimethyl-formamide;
DOI:10.1016/0008-6215(92)80042-Y