Phosphoric acid dibenzyl ester (1R,3R,4R,5R,7R,16R,17R,18R,19R)-19-benzyloxy-17,18-bis-(bis-benzyloxy-phosphoryloxy)-5-prop-2-ynyloxy-2,6,9,14,20-pentaoxa-tricyclo[14.3.1.0^3,7]icos-4-yl ester

Base Information

• Chemical Name: Phosphoric acid dibenzyl ester (1R,3R,4R,5R,7R,16R,17R,18R,19R)-19-benzyloxy-17,18-bis-(bis-benzyloxy-phosphoryloxy)-5-prop-2-ynyloxy-2,6,9,14,20-pentaoxa-tricyclo[14.3.1.0^3,7]icos-4-yl ester
• CAS No.: 300693-25-8
• Molecular Formula: C₆₇H₇₃O₁₉P₃
• Molecular Weight: 1275.23

Synonyms:

Chemical Property of Phosphoric acid dibenzyl ester (1R,3R,4R,5R,7R,16R,17R,18R,19R)-19-benzyloxy-17,18-bis-(bis-benzyloxy-phosphoryloxy)-5-prop-2-ynyloxy-2,6,9,14,20-pentaoxa-tricyclo[14.3.1.0^3,7]icos-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of Phosphoric acid dibenzyl ester (1R,3R,4R,5R,7R,16R,17R,18R,19R)-19-benzyloxy-17,18-bis-(bis-benzyloxy-phosphoryloxy)-5-prop-2-ynyloxy-2,6,9,14,20-pentaoxa-tricyclo[14.3.1.0^3,7]icos-4-yl ester

There total 14 articles about Phosphoric acid dibenzyl ester (1R,3R,4R,5R,7R,16R,17R,18R,19R)-19-benzyloxy-17,18-bis-(bis-benzyloxy-phosphoryloxy)-5-prop-2-ynyloxy-2,6,9,14,20-pentaoxa-tricyclo[14.3.1.0^3,7]icos-4-yl 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) → Phosphoric acid dibenzyl ester (1R,3R,4R,5R,7R,16R,17R,18R,19R)-19-benzyloxy-17,18-bis-(bis-benzyloxy-phosphoryloxy)-5-prop-2-ynyloxy-2,6,9,14,20-pentaoxa-tricyclo[14.3.1.03,7]icos-4-yl ester (300693-25-8)

Guidance literature:

Multi-step reaction with 11 steps

1: 4.40 g / NaH / dimethylformamide / 0 °C

2: 74 percent / TfOH / toluene; dioxane / 0.25 h

3: 95 percent / TBAF / tetrahydrofuran; dioxane / 16 h / 50 °C

4: 89 percent / sodium hydride / dimethylformamide / 3 h / cooling

5: 75 percent / RuCl₂(PCy₃)2CHPh / toluene / 16 h

6: 0.21 g / H₂ / PtO₂ / ethyl acetate

7: 92 percent / H₂O; ethane-1,2-diol / 1.5 h / Heating

8: 54 percent / TMSOTf / CH₂Cl₂ / 6 h

9: NaOMe / methanol / 1 h

10: 1H-tetrazole / 1,2-dichloro-ethane; acetonitrile / 0.5 h

11: 86 mg / t-BuOOH / 1,2-dichloro-ethane; acetonitrile / 0.5 h

With 1H-tetrazole; tert.-butylhydroperoxide; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; sodium hydride; Grubbs catalyst first generation; platinum(IV) oxide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; ethylene glycol; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile; 1: Substitution / 2: Substitution / 3: Hydrolysis / 4: Alkylation / 5: Cyclization / 6: Catalytic hydrogenation / 7: Acetylation / 8: Substitution / 9: Deacetylation / 10: Substitution / 11: Oxidation;

DOI:10.1016/S0040-4020(00)00480-4

Reference yield:

(2'S,3'S)-ethyl 3,4-di-O-(2',3'-dimethoxybutane-2',3'-diyl)-1-thio-β-D-glucopyranoside (197644-79-4) → Phosphoric acid dibenzyl ester (1R,3R,4R,5R,7R,16R,17R,18R,19R)-19-benzyloxy-17,18-bis-(bis-benzyloxy-phosphoryloxy)-5-prop-2-ynyloxy-2,6,9,14,20-pentaoxa-tricyclo[14.3.1.03,7]icos-4-yl ester (300693-25-8)

Guidance literature:

Multi-step reaction with 12 steps

1: pyridine / 2 h

2: 4.40 g / NaH / dimethylformamide / 0 °C

3: 74 percent / TfOH / toluene; dioxane / 0.25 h

4: 95 percent / TBAF / tetrahydrofuran; dioxane / 16 h / 50 °C

5: 89 percent / sodium hydride / dimethylformamide / 3 h / cooling

6: 75 percent / RuCl₂(PCy₃)2CHPh / toluene / 16 h

7: 0.21 g / H₂ / PtO₂ / ethyl acetate

8: 92 percent / H₂O; ethane-1,2-diol / 1.5 h / Heating

9: 54 percent / TMSOTf / CH₂Cl₂ / 6 h

10: NaOMe / methanol / 1 h

11: 1H-tetrazole / 1,2-dichloro-ethane; acetonitrile / 0.5 h

12: 86 mg / t-BuOOH / 1,2-dichloro-ethane; acetonitrile / 0.5 h

With pyridine; 1H-tetrazole; tert.-butylhydroperoxide; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; sodium hydride; Grubbs catalyst first generation; platinum(IV) oxide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; ethylene glycol; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile; 1: Substitution / 2: Substitution / 3: Substitution / 4: Hydrolysis / 5: Alkylation / 6: Cyclization / 7: Catalytic hydrogenation / 8: Acetylation / 9: Substitution / 10: Deacetylation / 11: Substitution / 12: Oxidation;

DOI:10.1016/S0040-4020(00)00480-4

Reference yield:

(2S,3S,4aR,5R,7S,8R,8aR)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-7-ethylsulfanyl-2,3-dimethoxy-2,3-dimethyl-hexahydro-pyrano[3,4-b][1,4]dioxin-8-ol → Phosphoric acid dibenzyl ester (1R,3R,4R,5R,7R,16R,17R,18R,19R)-19-benzyloxy-17,18-bis-(bis-benzyloxy-phosphoryloxy)-5-prop-2-ynyloxy-2,6,9,14,20-pentaoxa-tricyclo[14.3.1.03,7]icos-4-yl ester (300693-25-8)

Guidance literature:

Multi-step reaction with 11 steps

1: 4.40 g / NaH / dimethylformamide / 0 °C

2: 74 percent / TfOH / toluene; dioxane / 0.25 h

3: 95 percent / TBAF / tetrahydrofuran; dioxane / 16 h / 50 °C

4: 89 percent / sodium hydride / dimethylformamide / 3 h / cooling

5: 75 percent / RuCl₂(PCy₃)2CHPh / toluene / 16 h

6: 0.21 g / H₂ / PtO₂ / ethyl acetate

7: 92 percent / H₂O; ethane-1,2-diol / 1.5 h / Heating

8: 54 percent / TMSOTf / CH₂Cl₂ / 6 h

9: NaOMe / methanol / 1 h

10: 1H-tetrazole / 1,2-dichloro-ethane; acetonitrile / 0.5 h

11: 86 mg / t-BuOOH / 1,2-dichloro-ethane; acetonitrile / 0.5 h

With 1H-tetrazole; tert.-butylhydroperoxide; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; sodium hydride; Grubbs catalyst first generation; platinum(IV) oxide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; ethylene glycol; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile; 1: Substitution / 2: Substitution / 3: Hydrolysis / 4: Alkylation / 5: Cyclization / 6: Catalytic hydrogenation / 7: Acetylation / 8: Substitution / 9: Deacetylation / 10: Substitution / 11: Oxidation;

DOI:10.1016/S0040-4020(00)00480-4

upstream raw materials:

Dibenzyl N,N-diisopropylphosphoramidite

benzyl bromide

(2'S,3'S)-ethyl 3,4-di-O-(2',3'-dimethoxybutane-2',3'-diyl)-1-thio-β-D-glucopyranoside

[(2S,3S,4aR,5R,7R,8R,8aS)-8-Benzyloxy-7-((3aR,5R,6R,6aR)-5-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy)-2,3-dimethoxy-2,3-dimethyl-hexahydro-pyrano[3,4-b][1,4]dioxin-5-yl]-methanol

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