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

Base Information

Chemical Name:5-bromo-6-O-tert-butyldiphenylsilyl-5-deoxy-1,2-O-isopropylidene-β-L-talofuranose
CAS No.:141242-28-6
Molecular Formula:C₂₅H₃₃BrO₅Si
Molecular Weight:521.524
Hs Code.:

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

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Chemical Property of 5-bromo-6-O-tert-butyldiphenylsilyl-5-deoxy-1,2-O-isopropylidene-β-L-talofuranose

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Technology Process of 5-bromo-6-O-tert-butyldiphenylsilyl-5-deoxy-1,2-O-isopropylidene-β-L-talofuranose

There total 6 articles about 5-bromo-6-O-tert-butyldiphenylsilyl-5-deoxy-1,2-O-isopropylidene-β-L-talofuranose 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

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

Guidance literature:: Multi-step reaction with 4 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.

With phosphorus pentaoxide; sodium tetrahydroborate; N-Bromosuccinimide; sodium methylate; barium carbonate; zinc(II) chloride; In tetrachloromethane;
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

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

Guidance literature:: Multi-step reaction with 3 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.

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

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

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

Guidance literature:: Multi-step reaction with 5 steps

1: 99.7 percent / 4-dimethylaminopyridine / pyridine / 20 h / Ambient temperature

2: 94.4 percent / fused zinc chloride / 22 h / Ambient temperature

3: 74.1 percent / N-bromosuccinimide, barium carbonate / CCl₄ / 4 h / Heating

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

5: 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.

With dmap; phosphorus pentaoxide; sodium tetrahydroborate; N-Bromosuccinimide; sodium methylate; barium carbonate; zinc(II) chloride; In pyridine; tetrachloromethane;
DOI:10.1016/0008-6215(92)80042-Y