(2R/S,3S,4R)-1-bromo-3-benzyloxy-4,5-O-isopropylidene-2,4,5-trihydroxypentane

Base Information

Chemical Name:(2R/S,3S,4R)-1-bromo-3-benzyloxy-4,5-O-isopropylidene-2,4,5-trihydroxypentane
CAS No.:847380-72-7
Molecular Formula:C₁₅H₂₁BrO₄
Molecular Weight:345.233
Hs Code.:

Synonyms:(2R/S,3S,4R)-1-bromo-3-benzyloxy-4,5-O-isopropylidene-2,4,5-trihydroxypentane

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Chemical Property of (2R/S,3S,4R)-1-bromo-3-benzyloxy-4,5-O-isopropylidene-2,4,5-trihydroxypentane

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Technology Process of (2R/S,3S,4R)-1-bromo-3-benzyloxy-4,5-O-isopropylidene-2,4,5-trihydroxypentane

There total 4 articles about (2R/S,3S,4R)-1-bromo-3-benzyloxy-4,5-O-isopropylidene-2,4,5-trihydroxypentane 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: 94.0%

: 847380-71-6
(2R/S,3S,4R)-3-benzyloxy-1,2-epoxy-4,5-O-isopropylidene-4,5-dihydroxypentane

: 847380-72-7
(2R/S,3S,4R)-1-bromo-3-benzyloxy-4,5-O-isopropylidene-2,4,5-trihydroxypentane

Guidance literature:: With dilithium tetrabromonickelate(II); In tetrahydrofuran; at 20 ℃; for 16h;
DOI:10.1055/s-2004-834907

Reference yield:

: 18524-19-1
(S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-prop-2-en-1-ol

: 847380-72-7
(2R/S,3S,4R)-1-bromo-3-benzyloxy-4,5-O-isopropylidene-2,4,5-trihydroxypentane

Guidance literature:: Multi-step reaction with 3 steps

1.1: NaH / dimethylformamide

1.2: 4 g / dimethylformamide / 16 h / 40 °C

2.1: 90 percent / NaHCO₃; mCPBA / CH₂Cl₂ / 24 h / 20 °C

3.1: 94 percent / Li₂NiBr₄ / tetrahydrofuran / 16 h / 20 °C

With dilithium tetrabromonickelate(II); sodium hydride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1055/s-2004-834907

Reference yield:

: 71769-39-6
(2S,3S,4R)-1,2;3,4-di-O-isopropylidene-5-iodo-1,2,3,4-pentanetetrol

: 847380-72-7
(2R/S,3S,4R)-1-bromo-3-benzyloxy-4,5-O-isopropylidene-2,4,5-trihydroxypentane

Guidance literature:: Multi-step reaction with 4 steps

1.1: Zn / ethanol / 0.75 h / Heating

2.1: NaH / dimethylformamide

2.2: 4 g / dimethylformamide / 16 h / 40 °C

3.1: 90 percent / NaHCO₃; mCPBA / CH₂Cl₂ / 24 h / 20 °C

4.1: 94 percent / Li₂NiBr₄ / tetrahydrofuran / 16 h / 20 °C

With dilithium tetrabromonickelate(II); sodium hydride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; zinc; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1055/s-2004-834907