Phosphorous acid dibenzyl ester (1R,2S,3S,4R,5R,6S)-2,6-bis-benzyloxy-3,4,5-tris-(bis-benzyloxy-phosphanyloxy)-cyclohexyl ester

Base Information

• Chemical Name: Phosphorous acid dibenzyl ester (1R,2S,3S,4R,5R,6S)-2,6-bis-benzyloxy-3,4,5-tris-(bis-benzyloxy-phosphanyloxy)-cyclohexyl ester
• CAS No.: 117666-33-8
• Molecular Formula: C₇₆H₇₆O₁₄P₄
• Molecular Weight: 1337.33
• Mol file: 117666-33-8.mol

Synonyms:Phosphorous acid dibenzyl ester (1R,2S,3S,4R,5R,6S)-2,6-bis-benzyloxy-3,4,5-tris-(bis-benzyloxy-phosphanyloxy)-cyclohexyl ester

Chemical Property of Phosphorous acid dibenzyl ester (1R,2S,3S,4R,5R,6S)-2,6-bis-benzyloxy-3,4,5-tris-(bis-benzyloxy-phosphanyloxy)-cyclohexyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Phosphorous acid dibenzyl ester (1R,2S,3S,4R,5R,6S)-2,6-bis-benzyloxy-3,4,5-tris-(bis-benzyloxy-phosphanyloxy)-cyclohexyl ester

There total 18 articles about Phosphorous acid dibenzyl ester (1R,2S,3S,4R,5R,6S)-2,6-bis-benzyloxy-3,4,5-tris-(bis-benzyloxy-phosphanyloxy)-cyclohexyl 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:

benzyl bromide (100-39-0) → Phosphorous acid dibenzyl ester (1R,2S,3S,4R,5R,6S)-2,6-bis-benzyloxy-3,4,5-tris-(bis-benzyloxy-phosphanyloxy)-cyclohexyl ester (117666-33-8)

Guidance literature:

Multi-step reaction with 7 steps

1: NaH / dimethylformamide

2: 1M HCl / acetone / 0.5 h / Heating

3: pyridine / 10 h / 20 °C

4: NaOH / methanol

5: potassium tert-butoxide / dimethylsulfoxide

6: 1M HCl / methanol / 0.25 h / Heating

7: 1H-tetrazole / acetonitrile; CH₂Cl₂ / 1 h / 20 °C

With pyridine; 1H-tetrazole; hydrogenchloride; sodium hydroxide; potassium tert-butylate; sodium hydride; In methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1016/S0008-6215(00)90549-4

Reference yield:

(+)-1,3,4,5-tetra-O-allyl-2,6-di-O-benzyl-myo-inositol (117666-30-5) → Phosphorous acid dibenzyl ester (1R,2S,3S,4R,5R,6S)-2,6-bis-benzyloxy-3,4,5-tris-(bis-benzyloxy-phosphanyloxy)-cyclohexyl ester (117666-33-8)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene-p-sulphonic acid / 10percent Pd-C / ethanol; H₂O / 24 h / 95 °C

2: 1H-tetrazole / acetonitrile; CH₂Cl₂ / 1 h / 20 °C

With 1H-tetrazole; toluene-4-sulfonic acid; palladium on activated charcoal; In ethanol; dichloromethane; water; acetonitrile;

DOI:10.1016/S0008-6215(00)90549-4

Reference yield:

(+/-)-1,3,4,5-tetra-O-allyl-myo-inositol (136986-14-6,142436-08-6) → Phosphorous acid dibenzyl ester (1R,2S,3S,4R,5R,6S)-2,6-bis-benzyloxy-3,4,5-tris-(bis-benzyloxy-phosphanyloxy)-cyclohexyl ester (117666-33-8)

Guidance literature:

Multi-step reaction with 10 steps

1: NaH / dimethylformamide / 20 °C

2: 64 percent / toluene-p-sulphonic acid / 10percent Pd-C / ethanol; H₂O / 24 h / 95 °C

3: 900 mg / toluene-p-sulphonic acid / acetone / 6 h / 20 °C

4: NaH / dimethylformamide

5: 1M HCl / acetone / 0.5 h / Heating

6: pyridine / 10 h / 20 °C

7: NaOH / methanol

8: potassium tert-butoxide / dimethylsulfoxide

9: 1M HCl / methanol / 0.25 h / Heating

10: 1H-tetrazole / acetonitrile; CH₂Cl₂ / 1 h / 20 °C

With pyridine; 1H-tetrazole; hydrogenchloride; sodium hydroxide; potassium tert-butylate; sodium hydride; toluene-4-sulfonic acid; palladium on activated charcoal; In methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1016/S0008-6215(00)90549-4

upstream raw materials:

Dibenzyl N,N-diisopropylphosphoramidite

(-)-1L-2,6-di-O-benzyl-myo-inositol

dibenzyl N,N-diethylphosphoramidite

racemic 2,4-di-O-benzyl-myo-inositol

Downstream raw materials:

octabenzyl 1D-2,6-di-O-benzyl-myo-inositol 1,3,4,5-tetrakisphosphate

Refernces

• 1、 Dreef, C. E.,Tuinman, R. J.,Elie, C. J. J.,Marel, G. A. van der,Boom, J. H. van. "TOTAL SYNTHESIS OF OPTICALLY ACTIVE MYO-INOSITOL 1,4,5-TRISPHOSPHATE AND MYO-INOSITOL 1,3,4,5-TETRAKISPHOSPHATE". . p. 395 - 397. Retrieved 2007/10/02.