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

Base Information

• Chemical Name: Phosphoric acid dibenzyl ester (1R,2S,3R,4R,5S)-2-benzyloxy-5-benzyloxymethyl-3,4-bis-(bis-benzyloxy-phosphoryloxy)-cyclopentyl ester
• CAS No.: 221690-39-7
• Molecular Formula: C₆₂H₆₃O₁₄P₃
• Molecular Weight: 1125.1
• Mol file: 221690-39-7.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 10 articles about Phosphoric acid dibenzyl ester (1R,2S,3R,4R,5S)-2-benzyloxy-5-benzyloxymethyl-3,4-bis-(bis-benzyloxy-phosphoryloxy)-cyclopentyl ester 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) → Phosphoric acid dibenzyl ester (1R,2S,3R,4R,5S)-2-benzyloxy-5-benzyloxymethyl-3,4-bis-(bis-benzyloxy-phosphoryloxy)-cyclopentyl ester (221690-39-7)

Guidance literature:

Multi-step reaction with 8 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

8: 1.) 1H-tetrazole, 2.) m-CPBA / 1.) CH₂Cl₂, room temp., 2.) CH₂Cl₂, room temp.

With 1H-tetrazole; 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; 3-chloro-benzenecarboperoxoic acid; 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) → Phosphoric acid dibenzyl ester (1R,2S,3R,4R,5S)-2-benzyloxy-5-benzyloxymethyl-3,4-bis-(bis-benzyloxy-phosphoryloxy)-cyclopentyl ester (221690-39-7)

Guidance literature:

Multi-step reaction with 9 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

9: 1.) 1H-tetrazole, 2.) m-CPBA / 1.) CH₂Cl₂, room temp., 2.) CH₂Cl₂, room temp.

With 1H-tetrazole; 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; 3-chloro-benzenecarboperoxoic acid; 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) → Phosphoric acid dibenzyl ester (1R,2S,3R,4R,5S)-2-benzyloxy-5-benzyloxymethyl-3,4-bis-(bis-benzyloxy-phosphoryloxy)-cyclopentyl ester (221690-39-7)

Guidance literature:

Multi-step reaction with 7 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

7: 1.) 1H-tetrazole, 2.) m-CPBA / 1.) CH₂Cl₂, room temp., 2.) CH₂Cl₂, room temp.

With 1H-tetrazole; hydrogenchloride; lithium aluminium tetrahydride; aluminium trichloride; samarium diiodide; oxalyl dichloride; sodium hydride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; 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:

Dibenzyl N,N-diisopropylphosphoramidite

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

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

p-Anisaldehyde dimethyl acetal