5-azido-6-O-tert-butyldiphenylsilyl-5-deoxy-1,2-O-isopropylidene-α-D-allofuranose

Base Information

Chemical Name:5-azido-6-O-tert-butyldiphenylsilyl-5-deoxy-1,2-O-isopropylidene-α-D-allofuranose
CAS No.:141242-29-7
Molecular Formula:C₂₅H₃₃N₃O₅Si
Molecular Weight:483.64
Hs Code.:

Synonyms:5-azido-6-O-tert-butyldiphenylsilyl-5-deoxy-1,2-O-isopropylidene-α-D-allofuranose

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Chemical Property of 5-azido-6-O-tert-butyldiphenylsilyl-5-deoxy-1,2-O-isopropylidene-α-D-allofuranose

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Technology Process of 5-azido-6-O-tert-butyldiphenylsilyl-5-deoxy-1,2-O-isopropylidene-α-D-allofuranose

There total 7 articles about 5-azido-6-O-tert-butyldiphenylsilyl-5-deoxy-1,2-O-isopropylidene-α-D-allofuranose 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: 71.9%

: 141242-28-6
5-bromo-6-O-tert-butyldiphenylsilyl-5-deoxy-1,2-O-isopropylidene-β-L-talofuranose

: 141242-29-7
5-azido-6-O-tert-butyldiphenylsilyl-5-deoxy-1,2-O-isopropylidene-α-D-allofuranose

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide; at 90 ℃; for 17h;
DOI:10.1016/0008-6215(92)80042-Y

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

: 141242-29-7
5-azido-6-O-tert-butyldiphenylsilyl-5-deoxy-1,2-O-isopropylidene-α-D-allofuranose

Guidance literature:: Multi-step reaction with 5 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

With phosphorus pentaoxide; sodium tetrahydroborate; N-Bromosuccinimide; sodium azide; 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

: 141242-29-7
5-azido-6-O-tert-butyldiphenylsilyl-5-deoxy-1,2-O-isopropylidene-α-D-allofuranose

Guidance literature:: Multi-step reaction with 4 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

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