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

Base Information

Chemical Name:6-O-benzyl-1,2-O-isopropylidene-3-O-(2-methyl-1-propenyl)-α-D-glucofuranose
CAS No.:552849-08-8
Molecular Formula:C₂₀H₂₈O₆
Molecular Weight:364.439
Hs Code.:

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

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Chemical Property of 6-O-benzyl-1,2-O-isopropylidene-3-O-(2-methyl-1-propenyl)-α-D-glucofuranose

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Technology Process of 6-O-benzyl-1,2-O-isopropylidene-3-O-(2-methyl-1-propenyl)-α-D-glucofuranose

There total 4 articles about 6-O-benzyl-1,2-O-isopropylidene-3-O-(2-methyl-1-propenyl)-α-D-glucofuranose 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: 55.0%

: 100-39-0
benzyl bromide

: 552849-06-6
1,2-O-isopropylidene-3-O-(2-methyl-1-propenyl)-α-D-glucofuranose

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

Guidance literature:: 1,2-O-isopropylidene-3-O-(2-methyl-1-propenyl)-α-D-glucofuranose; With di(n-butyl)tin oxide; In benzene; for 2h; Heating;

benzyl bromide; With tetra-(n-butyl)ammonium iodide; In benzene; Heating;
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

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

Guidance literature:: Multi-step reaction with 3 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

With potassium tert-butylate; di(n-butyl)tin oxide; acetic acid; In tetrahydrofuran; dimethyl sulfoxide; benzene;
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

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

Guidance literature:: Multi-step reaction with 2 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

With di(n-butyl)tin oxide; acetic acid; In tetrahydrofuran; benzene;
DOI:10.1021/jo034159g