(1R,2S,3S,4R,5R)-3-Benzyloxy-5-benzyloxymethyl-cyclopentane-1,2,4-triol

Base Information

• Chemical Name: (1R,2S,3S,4R,5R)-3-Benzyloxy-5-benzyloxymethyl-cyclopentane-1,2,4-triol
• CAS No.: 183170-53-8
• Molecular Formula: C₂₀H₂₄O₅
• Molecular Weight: 344.408
• Mol file: 183170-53-8.mol

Synonyms:

Chemical Property of (1R,2S,3S,4R,5R)-3-Benzyloxy-5-benzyloxymethyl-cyclopentane-1,2,4-triol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,3S,4R,5R)-3-Benzyloxy-5-benzyloxymethyl-cyclopentane-1,2,4-triol

There total 8 articles about (1R,2S,3S,4R,5R)-3-Benzyloxy-5-benzyloxymethyl-cyclopentane-1,2,4-triol 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:

methyl 4,6-O-para-methoxybenzylidene-α-D-glucopyranoside (18929-63-0) → (1R,2S,3S,4R,5R)-3-Benzyloxy-5-benzyloxymethyl-cyclopentane-1,2,4-triol (183170-53-8)

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: 37 percent / SmI₂, t-BuOH / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h

6: 28 percent / NaH / dimethylformamide / 1 h / 0 °C

7: aq. HCl / ethanol / Heating

With hydrogenchloride; lithium aluminium tetrahydride; aluminium trichloride; samarium diiodide; oxalyl dichloride; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; dimethyl sulfoxide; triethylamine; tert-butyl alcohol; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jo961158y

Reference yield:

p-Anisaldehyde dimethyl acetal (2186-92-7) → (1R,2S,3S,4R,5R)-3-Benzyloxy-5-benzyloxymethyl-cyclopentane-1,2,4-triol (183170-53-8)

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: 37 percent / SmI₂, t-BuOH / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h

7: 28 percent / NaH / dimethylformamide / 1 h / 0 °C

8: aq. HCl / ethanol / Heating

With hydrogenchloride; lithium aluminium tetrahydride; aluminium trichloride; samarium diiodide; oxalyl dichloride; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; tert-butyl alcohol; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jo961158y

Reference yield:

methyl 2-O-benzyl-4,6-O-(p-methoxybenzylidene)-α-D-glucopyranoside (299199-12-5) → (1R,2S,3S,4R,5R)-3-Benzyloxy-5-benzyloxymethyl-cyclopentane-1,2,4-triol (183170-53-8)

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: 37 percent / SmI₂, t-BuOH / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h

5: 28 percent / NaH / dimethylformamide / 1 h / 0 °C

6: aq. HCl / ethanol / Heating

With hydrogenchloride; lithium aluminium tetrahydride; aluminium trichloride; samarium diiodide; oxalyl dichloride; sodium hydride; dimethyl sulfoxide; triethylamine; tert-butyl alcohol; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jo961158y

upstream raw materials:

methyl 4,6-O-para-methoxybenzylidene-α-D-glucopyranoside

p-Anisaldehyde dimethyl acetal

methyl 2-O-benzyl-3,4-bis-O-(p-methoxybenzyl)-α-D-gluco-hexodialdopyranoside (1,5)

methyl 2-O-benzyl-3,4-bis-O-(p-methoxybenzyl)-α-D-glucopyranoside

Downstream raw materials:

Phosphoric acid dibenzyl ester (1R,2S,3R,4R,5S)-2-benzyloxy-5-benzyloxymethyl-3,4-bis-(bis-benzyloxy-phosphoryloxy)-cyclopentyl ester