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

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Chemical Name:Phosphoric acid dibenzyl ester (1R,2S,3R,4R,5R,6S)-2,3,6-tris-benzyloxy-4,5-bis-(bis-benzyloxy-phosphoryloxy)-cyclohexyl ester
CAS No.:185022-24-6
Molecular Formula:C₆₉H₆₉O₁₅P₃
Molecular Weight:1231.22
Hs Code.:

Synonyms:

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

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

There total 10 articles about Phosphoric acid dibenzyl ester (1R,2S,3R,4R,5R,6S)-2,3,6-tris-benzyloxy-4,5-bis-(bis-benzyloxy-phosphoryloxy)-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:

: 100-39-0
benzyl bromide

: 185022-24-6
Phosphoric acid dibenzyl ester (1R,2S,3R,4R,5R,6S)-2,3,6-tris-benzyloxy-4,5-bis-(bis-benzyloxy-phosphoryloxy)-cyclohexyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) NaH / 1) DMF, rt; 2) DMF, rt, 2 h

2: 88 percent / HCl / methanol / 0.75 h / 50 °C

3: 35 percent / DMAP, DCC / CH₂Cl₂ / -20 °C

4: 98 percent / NaOH / methanol / 0.5 h / Heating

5: 1.) NaH / 1) DMF, rt; 2) DMF, rt, 2 h

6: 71 percent / potassium tert-butoxide / dimethylsulfoxide / 5 h / 50 °C

7: 1.) 1H-tetrazole, 2.) tert-butyl hydroperoxide / 1) CH₂Cl₂, rt, 15 min; 2) CH₂Cl₂, -78 deg C, 30 min

With 1H-tetrazole; hydrogenchloride; tert.-butylhydroperoxide; dmap; sodium hydroxide; potassium tert-butylate; sodium hydride; dicyclohexyl-carbodiimide; In methanol; dichloromethane; dimethyl sulfoxide;
DOI:10.1021/jo961280x

Reference yield:

: 98906-32-2
(±)-1,4-di-O-allyl-2,3:5,6-di-O-isopropylidene-myo-inositol

: 185022-24-6
Phosphoric acid dibenzyl ester (1R,2S,3R,4R,5R,6S)-2,3,6-tris-benzyloxy-4,5-bis-(bis-benzyloxy-phosphoryloxy)-cyclohexyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 68 percent / toluene-p-sulfonic acid / ethane-1,2-diol; CH₂Cl₂ / 0.17 h / 0 °C

2: 52 percent / dibutyltin oxide, tetrabutylammonium iodide / acetonitrile / 48 h / Heating

3: 1.) NaH / 1) DMF, rt; 2) DMF, rt, 2 h

4: 88 percent / HCl / methanol / 0.75 h / 50 °C

5: 35 percent / DMAP, DCC / CH₂Cl₂ / -20 °C

6: 98 percent / NaOH / methanol / 0.5 h / Heating

7: 1.) NaH / 1) DMF, rt; 2) DMF, rt, 2 h

8: 71 percent / potassium tert-butoxide / dimethylsulfoxide / 5 h / 50 °C

9: 1.) 1H-tetrazole, 2.) tert-butyl hydroperoxide / 1) CH₂Cl₂, rt, 15 min; 2) CH₂Cl₂, -78 deg C, 30 min

With 1H-tetrazole; hydrogenchloride; tert.-butylhydroperoxide; dmap; sodium hydroxide; potassium tert-butylate; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; In methanol; dichloromethane; ethylene glycol; dimethyl sulfoxide; acetonitrile;
DOI:10.1021/jo961280x

Reference yield:

: 98906-33-3,115116-24-0
(±)-1,4-di-O-allyl-2,3-O-isopropylidene-myo-inositol

: 185022-24-6
Phosphoric acid dibenzyl ester (1R,2S,3R,4R,5R,6S)-2,3,6-tris-benzyloxy-4,5-bis-(bis-benzyloxy-phosphoryloxy)-cyclohexyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 52 percent / dibutyltin oxide, tetrabutylammonium iodide / acetonitrile / 48 h / Heating

2: 1.) NaH / 1) DMF, rt; 2) DMF, rt, 2 h

3: 88 percent / HCl / methanol / 0.75 h / 50 °C

4: 35 percent / DMAP, DCC / CH₂Cl₂ / -20 °C

5: 98 percent / NaOH / methanol / 0.5 h / Heating

6: 1.) NaH / 1) DMF, rt; 2) DMF, rt, 2 h

7: 71 percent / potassium tert-butoxide / dimethylsulfoxide / 5 h / 50 °C

8: 1.) 1H-tetrazole, 2.) tert-butyl hydroperoxide / 1) CH₂Cl₂, rt, 15 min; 2) CH₂Cl₂, -78 deg C, 30 min

With 1H-tetrazole; hydrogenchloride; tert.-butylhydroperoxide; dmap; sodium hydroxide; potassium tert-butylate; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; dicyclohexyl-carbodiimide; In methanol; dichloromethane; dimethyl sulfoxide; acetonitrile;
DOI:10.1021/jo961280x