Diethyl (3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranos-6-yl)malonate

Base Information

Chemical Name:Diethyl (3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranos-6-yl)malonate
CAS No.:360562-24-9
Molecular Formula:C₂₃H₃₂O₈
Molecular Weight:436.502
Hs Code.:

Synonyms:Diethyl (3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranos-6-yl)malonate

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Chemical Property of Diethyl (3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranos-6-yl)malonate

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Technology Process of Diethyl (3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranos-6-yl)malonate

There total 6 articles about Diethyl (3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranos-6-yl)malonate 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: 87.0%

: 105-53-3
diethyl malonate

: 360562-23-8
3-O-Benzyl-5-deoxy-1,2-O-isopropylidene-6-iodo-α-D-xylo-hexofuranose

: 360562-24-9
Diethyl (3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranos-6-yl)malonate

Guidance literature:: diethyl malonate; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.25h;

3-O-Benzyl-5-deoxy-1,2-O-isopropylidene-6-iodo-α-D-xylo-hexofuranose; In N,N-dimethyl-formamide; at 20 ℃; for 6h;
DOI:10.1135/cccc20010785

Reference yield:

: 37776-15-1
6-O-Benzoyl-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose

: 360562-24-9
Diethyl (3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranos-6-yl)malonate

Guidance literature:: Multi-step reaction with 6 steps

1.1: NaH / dimethylformamide / 0.5 h / 0 °C

1.2: 91 percent / dimethylformamide / 1 h / 0 - 20 °C

2.1: Bu₃SnH; AIBN / toluene / 0.5 h / Heating

3.1: 9.85 g / NaOMe / methanol

4.1: 92 percent / DMAP; pyridine / 20 °C

5.1: 89 percent / NaI / butan-2-one / 1 h / Heating

6.1: NaH / dimethylformamide / 0.25 h / 0 °C

6.2: 87 percent / dimethylformamide / 6 h / 20 °C

With pyridine; dmap; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium methylate; sodium hydride; sodium iodide; In methanol; N,N-dimethyl-formamide; toluene; butanone;
DOI:10.1135/cccc20010785

Reference yield:

: 57575-19-6,81686-55-7
2-[(3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethanol

: 360562-24-9
Diethyl (3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranos-6-yl)malonate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 92 percent / DMAP; pyridine / 20 °C

2.1: 89 percent / NaI / butan-2-one / 1 h / Heating

3.1: NaH / dimethylformamide / 0.25 h / 0 °C

3.2: 87 percent / dimethylformamide / 6 h / 20 °C

With pyridine; dmap; sodium hydride; sodium iodide; In N,N-dimethyl-formamide; butanone;
DOI:10.1135/cccc20010785