O-benzyl-3-dibromo-6,6-didesoxy-5,6-O-isopropylidene-1,2-α-D-xylo-hexeno-5-furannose-1,4

Base Information

Chemical Name:O-benzyl-3-dibromo-6,6-didesoxy-5,6-O-isopropylidene-1,2-α-D-xylo-hexeno-5-furannose-1,4
CAS No.:53931-26-3
Molecular Formula:C₁₆H₁₈Br₂O₄
Molecular Weight:434.125
Hs Code.:

Synonyms:O-benzyl-3-dibromo-6,6-didesoxy-5,6-O-isopropylidene-1,2-α-D-xylo-hexeno-5-furannose-1,4

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Chemical Property of O-benzyl-3-dibromo-6,6-didesoxy-5,6-O-isopropylidene-1,2-α-D-xylo-hexeno-5-furannose-1,4

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Technology Process of O-benzyl-3-dibromo-6,6-didesoxy-5,6-O-isopropylidene-1,2-α-D-xylo-hexeno-5-furannose-1,4

There total 6 articles about O-benzyl-3-dibromo-6,6-didesoxy-5,6-O-isopropylidene-1,2-α-D-xylo-hexeno-5-furannose-1,4 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: 96.0%

: 558-13-4
carbon tetrabromide

: 23558-05-6
3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose

: 53931-26-3
O-benzyl-3-dibromo-6,6-didesoxy-5,6-O-isopropylidene-1,2-α-D-xylo-hexeno-5-furannose-1,4

Guidance literature:: carbon tetrabromide; With triphenylphosphine; zinc; In dichloromethane; at 0 ℃; for 0.25h;

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose; In dichloromethane; at 0 - 20 ℃; for 13h;
DOI:10.1021/ol0701159

Reference yield:

: 22529-61-9
(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol

: 53931-26-3
O-benzyl-3-dibromo-6,6-didesoxy-5,6-O-isopropylidene-1,2-α-D-xylo-hexeno-5-furannose-1,4

Guidance literature:: Multi-step reaction with 2 steps

1.1: 88 percent / silica-supported NaIO₄ / CH₂Cl₂ / 2 h / 20 °C

2.1: triphenylphosphine; zinc / CH₂Cl₂ / 0.25 h / 0 °C

2.2: 96 percent / CH₂Cl₂ / 13 h / 0 - 20 °C

With sodium periodate; silica gel; triphenylphosphine; zinc; In dichloromethane;
DOI:10.1021/ol0701159

Reference yield:

: 100-39-0
benzyl bromide

: 53931-26-3
O-benzyl-3-dibromo-6,6-didesoxy-5,6-O-isopropylidene-1,2-α-D-xylo-hexeno-5-furannose-1,4

Guidance literature:: Multi-step reaction with 4 steps

1.1: 93 percent / NaH; Bu₄NI / tetrahydrofuran; various solvent(s) / 20 h / 0 - 25 °C

2.1: 82 percent / aq. acetic acid / 8 h / 20 °C

3.1: 88 percent / silica-supported NaIO₄ / CH₂Cl₂ / 2 h / 20 °C

4.1: triphenylphosphine; zinc / CH₂Cl₂ / 0.25 h / 0 °C

4.2: 96 percent / CH₂Cl₂ / 13 h / 0 - 20 °C

With sodium periodate; silica gel; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; triphenylphosphine; zinc; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol0701159