(1R,2S,3S,4R,5S)-3,4-bis(benzyloxy)-1,2-bis[(p-methoxybenzyl)oxy]-5-vinylcyclopentane

Base Information

Chemical Name:(1R,2S,3S,4R,5S)-3,4-bis(benzyloxy)-1,2-bis[(p-methoxybenzyl)oxy]-5-vinylcyclopentane
CAS No.:183170-49-2
Molecular Formula:C₃₇H₄₀O₆
Molecular Weight:580.721
Hs Code.:

Synonyms:

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Chemical Property of (1R,2S,3S,4R,5S)-3,4-bis(benzyloxy)-1,2-bis[(p-methoxybenzyl)oxy]-5-vinylcyclopentane

Chemical Property:

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Technology Process of (1R,2S,3S,4R,5S)-3,4-bis(benzyloxy)-1,2-bis[(p-methoxybenzyl)oxy]-5-vinylcyclopentane

There total 10 articles about (1R,2S,3S,4R,5S)-3,4-bis(benzyloxy)-1,2-bis[(p-methoxybenzyl)oxy]-5-vinylcyclopentane 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:

: 18929-63-0
methyl 4,6-O-para-methoxybenzylidene-α-D-glucopyranoside

: 183170-49-2
(1R,2S,3S,4R,5S)-3,4-bis(benzyloxy)-1,2-bis[(p-methoxybenzyl)oxy]-5-vinylcyclopentane

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) dibutyltin oxide, tetrabutylammonium iodide / 1.) MeCN, reflux, 2 h, 2.) MeCN, reflux, 16 h

2: 87 percent / NaH / dimethylformamide / 3 h / Ambient temperature

3: 1.) LiAlH₄, 2.) AlCl₃ / 1.) THF, reflux, 1 h, 2.) THF, reflux, 2.5 h

4: 1.) DMSO, oxalyl chloride, 2.) triethylamine / 1.) CH₂Cl₂, -60 deg C, 20 min, 2.) CH₂Cl₂, -60 deg C, 10 min

5: 86 percent / potassium tert-butoxide / tetrahydrofuran / 1 h / Ambient temperature

6: 1.) zirconocene dichloride, n-BuLi, 2.) BF₃*Et₂O / 1.) THF, room temp., 3 h, 2.) THF, room temp., 30 min

7: NaH / dimethylformamide

With lithium aluminium tetrahydride; n-butyllithium; aluminium trichloride; oxalyl dichloride; zirconocene dichloride; boron trifluoride diethyl etherate; potassium tert-butylate; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1021/jo961158y

Reference yield:

: 2186-92-7
p-Anisaldehyde dimethyl acetal

: 183170-49-2
(1R,2S,3S,4R,5S)-3,4-bis(benzyloxy)-1,2-bis[(p-methoxybenzyl)oxy]-5-vinylcyclopentane

Guidance literature:: Multi-step reaction with 8 steps

1: 84 percent / p-toluenesulfonic acid / dimethylformamide / 4 h / 70 °C

2: 1.) dibutyltin oxide, tetrabutylammonium iodide / 1.) MeCN, reflux, 2 h, 2.) MeCN, reflux, 16 h

3: 87 percent / NaH / dimethylformamide / 3 h / Ambient temperature

4: 1.) LiAlH₄, 2.) AlCl₃ / 1.) THF, reflux, 1 h, 2.) THF, reflux, 2.5 h

5: 1.) DMSO, oxalyl chloride, 2.) triethylamine / 1.) CH₂Cl₂, -60 deg C, 20 min, 2.) CH₂Cl₂, -60 deg C, 10 min

6: 86 percent / potassium tert-butoxide / tetrahydrofuran / 1 h / Ambient temperature

7: 1.) zirconocene dichloride, n-BuLi, 2.) BF₃*Et₂O / 1.) THF, room temp., 3 h, 2.) THF, room temp., 30 min

8: NaH / dimethylformamide

With lithium aluminium tetrahydride; n-butyllithium; aluminium trichloride; oxalyl dichloride; zirconocene dichloride; boron trifluoride diethyl etherate; potassium tert-butylate; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1021/jo961158y

Reference yield:

: 824-94-2
p-methoxybenzyl chloride

: 183170-49-2
(1R,2S,3S,4R,5S)-3,4-bis(benzyloxy)-1,2-bis[(p-methoxybenzyl)oxy]-5-vinylcyclopentane

Guidance literature:: Multi-step reaction with 6 steps

1: 87 percent / NaH / dimethylformamide / 3 h / Ambient temperature

2: 1.) LiAlH₄, 2.) AlCl₃ / 1.) THF, reflux, 1 h, 2.) THF, reflux, 2.5 h

3: 1.) DMSO, oxalyl chloride, 2.) triethylamine / 1.) CH₂Cl₂, -60 deg C, 20 min, 2.) CH₂Cl₂, -60 deg C, 10 min

4: 86 percent / potassium tert-butoxide / tetrahydrofuran / 1 h / Ambient temperature

5: 1.) zirconocene dichloride, n-BuLi, 2.) BF₃*Et₂O / 1.) THF, room temp., 3 h, 2.) THF, room temp., 30 min

6: NaH / dimethylformamide

With lithium aluminium tetrahydride; n-butyllithium; aluminium trichloride; oxalyl dichloride; zirconocene dichloride; boron trifluoride diethyl etherate; potassium tert-butylate; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1021/jo961158y