6-O-benzyl-1,2-O-isopropylidene-3-O-(2-methyl-1-propenyl)-5-oxo-α-D-xylo-hexofuranose

Base Information

Chemical Name:6-O-benzyl-1,2-O-isopropylidene-3-O-(2-methyl-1-propenyl)-5-oxo-α-D-xylo-hexofuranose
CAS No.:552848-91-6
Molecular Formula:C₂₀H₂₆O₆
Molecular Weight:362.423
Hs Code.:

Synonyms:6-O-benzyl-1,2-O-isopropylidene-3-O-(2-methyl-1-propenyl)-5-oxo-α-D-xylo-hexofuranose

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Chemical Property of 6-O-benzyl-1,2-O-isopropylidene-3-O-(2-methyl-1-propenyl)-5-oxo-α-D-xylo-hexofuranose

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Technology Process of 6-O-benzyl-1,2-O-isopropylidene-3-O-(2-methyl-1-propenyl)-5-oxo-α-D-xylo-hexofuranose

There total 5 articles about 6-O-benzyl-1,2-O-isopropylidene-3-O-(2-methyl-1-propenyl)-5-oxo-α-D-xylo-hexofuranose 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: 70.0%

: 552849-08-8
6-O-benzyl-1,2-O-isopropylidene-3-O-(2-methyl-1-propenyl)-α-D-glucofuranose

: 552848-91-6
6-O-benzyl-1,2-O-isopropylidene-3-O-(2-methyl-1-propenyl)-5-oxo-α-D-xylo-hexofuranose

Guidance literature:: With Dess-Martin periodane; In acetonitrile; tert-butyl alcohol; at 20 ℃; for 16h;
DOI:10.1021/jo034159g

Reference yield:

: 20771-03-3
(3aR,5R,6S,6aR)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-((2-methylprop-1-en-1-yl)oxy)tetrahydrofuro[2,3-d][1,3]dioxole

: 552848-91-6
6-O-benzyl-1,2-O-isopropylidene-3-O-(2-methyl-1-propenyl)-5-oxo-α-D-xylo-hexofuranose

Guidance literature:: Multi-step reaction with 3 steps

1.1: 100 percent / aq. AcOH / tetrahydrofuran / 7 h / 60 °C

2.1: n-Bu₂SnO / benzene / 2 h / Heating

2.2: 55 percent / n-Bu₄NI / benzene / Heating

3.1: 70 percent / Dess-Martin periodinane / 2-methyl-propan-2-ol; acetonitrile / 16 h / 20 °C

With di(n-butyl)tin oxide; Dess-Martin periodane; acetic acid; In tetrahydrofuran; acetonitrile; tert-butyl alcohol; benzene; 3.1: Dess-Martin oxidation;
DOI:10.1021/jo034159g

Reference yield:

: 20771-02-2
5-[2,2-dimethyl-(4R)-1,3-dioxolan-4-yl]-2,2-dimethyl-(3aR,5R,6S,6aR)-perhydrofuro[2,3-d][1,3]dioxol-6-yl 2-methylallyl ether

: 552848-91-6
6-O-benzyl-1,2-O-isopropylidene-3-O-(2-methyl-1-propenyl)-5-oxo-α-D-xylo-hexofuranose

Guidance literature:: Multi-step reaction with 4 steps

1.1: 78 percent / t-BuOK / dimethylsulfoxide / 20 h / 100 °C

2.1: 100 percent / aq. AcOH / tetrahydrofuran / 7 h / 60 °C

3.1: n-Bu₂SnO / benzene / 2 h / Heating

3.2: 55 percent / n-Bu₄NI / benzene / Heating

4.1: 70 percent / Dess-Martin periodinane / 2-methyl-propan-2-ol; acetonitrile / 16 h / 20 °C

With potassium tert-butylate; di(n-butyl)tin oxide; Dess-Martin periodane; acetic acid; In tetrahydrofuran; dimethyl sulfoxide; acetonitrile; tert-butyl alcohol; benzene; 4.1: Dess-Martin oxidation;
DOI:10.1021/jo034159g