Acetic acid (2R,3S,4R,5R,6R)-4,5-bis-(3-oxo-1,5-dihydro-3λ⁵-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-2-[3-(3-oxo-1,5-dihydro-3λ⁵-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-propyl]-6-trityloxymethyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3S,4R,5R,6R)-4,5-bis-(3-oxo-1,5-dihydro-3λ⁵-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-2-[3-(3-oxo-1,5-dihydro-3λ⁵-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-propyl]-6-trityloxymethyl-tetrahydro-pyran-3-yl ester
• CAS No.: 851392-49-9
• Molecular Formula: C₅₄H₅₅O₁₆P₃
• Molecular Weight: 1052.94

Synonyms:Acetic acid (2R,3S,4R,5R,6R)-4,5-bis-(3-oxo-1,5-dihydro-3λ⁵-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-2-[3-(3-oxo-1,5-dihydro-3λ⁵-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-propyl]-6-trityloxymethyl-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2R,3S,4R,5R,6R)-4,5-bis-(3-oxo-1,5-dihydro-3λ⁵-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-2-[3-(3-oxo-1,5-dihydro-3λ⁵-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-propyl]-6-trityloxymethyl-tetrahydro-pyran-3-yl ester

Chemical Property:

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Technology Process of Acetic acid (2R,3S,4R,5R,6R)-4,5-bis-(3-oxo-1,5-dihydro-3λ⁵-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-2-[3-(3-oxo-1,5-dihydro-3λ⁵-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-propyl]-6-trityloxymethyl-tetrahydro-pyran-3-yl ester

There total 10 articles about Acetic acid (2R,3S,4R,5R,6R)-4,5-bis-(3-oxo-1,5-dihydro-3λ⁵-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-2-[3-(3-oxo-1,5-dihydro-3λ⁵-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-propyl]-6-trityloxymethyl-tetrahydro-pyran-3-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:

phenyl 2-O-(allyl(dimethyl)silyl)-3,4-bis-O-(tert-butyl(dimethyl)silyl)-6-O-(triphenylmethyl)-1-seleno-β-D-glucopyranoside (288585-02-4) → Acetic acid (2R,3S,4R,5R,6R)-4,5-bis-(3-oxo-1,5-dihydro-3λ5-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-2-[3-(3-oxo-1,5-dihydro-3λ5-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-propyl]-6-trityloxymethyl-tetrahydro-pyran-3-yl ester (851392-49-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 97 percent / Bu₃SnH; AIBN / benzene / 2 h / Heating

2: tetrahydrofuran; diethyl ether / 0.08 h / -20 °C

3: pyridine / 12 h / 20 °C

4: 61 percent / AcOOH; AcONa; AcOH / KBr; H₂SO₄ / 14 h / 0 - 20 °C

5: 99 percent / TBAF; AcOH / tetrahydrofuran / 12 h / 20 °C

6: 1H-tetrazole / CH₂Cl₂ / 0.5 h / 0 °C

7: m-CPBA / CH₂Cl₂; H₂O / 0.5 h / -40 - 20 °C

With pyridine; 1H-tetrazole; peracetic acid; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium acetate; acetic acid; 3-chloro-benzenecarboperoxoic acid; sulfuric acid; potassium bromide; In tetrahydrofuran; diethyl ether; dichloromethane; water; benzene; 4: Fleming oxidation;

DOI:10.1016/j.tet.2005.02.025

Reference yield:

phenyl 3,4-bis-O-tert-butyldimethylsilyl-6-O-trityl-1-seleno-β-D-glucose (288584-99-6) → Acetic acid (2R,3S,4R,5R,6R)-4,5-bis-(3-oxo-1,5-dihydro-3λ5-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-2-[3-(3-oxo-1,5-dihydro-3λ5-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-propyl]-6-trityloxymethyl-tetrahydro-pyran-3-yl ester (851392-49-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 97 percent / pyridine; molecular sieves 3 Angstroem / 1 h / 20 °C

2: 97 percent / Bu₃SnH; AIBN / benzene / 2 h / Heating

3: tetrahydrofuran; diethyl ether / 0.08 h / -20 °C

4: pyridine / 12 h / 20 °C

5: 61 percent / AcOOH; AcONa; AcOH / KBr; H₂SO₄ / 14 h / 0 - 20 °C

6: 99 percent / TBAF; AcOH / tetrahydrofuran / 12 h / 20 °C

7: 1H-tetrazole / CH₂Cl₂ / 0.5 h / 0 °C

8: m-CPBA / CH₂Cl₂; H₂O / 0.5 h / -40 - 20 °C

With pyridine; 1H-tetrazole; peracetic acid; 2,2'-azobis(isobutyronitrile); 3 A molecular sieve; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium acetate; acetic acid; 3-chloro-benzenecarboperoxoic acid; sulfuric acid; potassium bromide; In tetrahydrofuran; diethyl ether; dichloromethane; water; benzene; 5: Fleming oxidation;

DOI:10.1016/j.tet.2005.02.025

Reference yield:

(2R,3R,4R,4aS,9aR)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-6,6-dimethyl-2-trityloxymethyl-octahydro-1,5-dioxa-6-sila-benzocycloheptene (288585-04-6) → Acetic acid (2R,3S,4R,5R,6R)-4,5-bis-(3-oxo-1,5-dihydro-3λ5-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-2-[3-(3-oxo-1,5-dihydro-3λ5-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-propyl]-6-trityloxymethyl-tetrahydro-pyran-3-yl ester (851392-49-9)

Guidance literature:

Multi-step reaction with 6 steps

1: tetrahydrofuran; diethyl ether / 0.08 h / -20 °C

2: pyridine / 12 h / 20 °C

3: 61 percent / AcOOH; AcONa; AcOH / KBr; H₂SO₄ / 14 h / 0 - 20 °C

4: 99 percent / TBAF; AcOH / tetrahydrofuran / 12 h / 20 °C

5: 1H-tetrazole / CH₂Cl₂ / 0.5 h / 0 °C

6: m-CPBA / CH₂Cl₂; H₂O / 0.5 h / -40 - 20 °C

With pyridine; 1H-tetrazole; peracetic acid; tetrabutyl ammonium fluoride; sodium acetate; acetic acid; 3-chloro-benzenecarboperoxoic acid; sulfuric acid; potassium bromide; In tetrahydrofuran; diethyl ether; dichloromethane; water; 3: Fleming oxidation;

DOI:10.1016/j.tet.2005.02.025

upstream raw materials:

4,8-anhydro-4-O-acetyl-9-O-triphenylmethyl-2,3-dideoxy-D-glycero-D-ido-nonitol

4,8-anhydro-4-O-acetyl-6,7-di-O-(tert-butyl(dimethyl)silyl)-9-O-triphenylmethyl-2,3-dideoxy-D-glycero-D-ido-nonitol

(2R,3S,4R,5R,6R)-3-acetoxy-6-(triphenylmethoxy)methyl-4,5-bis-O-(tert-butyl(dimethyl)silyloxy)-2-[3-(dimethyl(phenyl)silyl)propyl]tetrahydropyran

(2R,3S,4R,5R,6R)-3-acetoxy-6-(triphenylmethoxy)methyl-4,5-bis-O-(tert-butyl(dimethyl)silyloxy)-2-[3-(dimethyl(p-methoxyphenyl)silyl)propyl]tetrahydropyran

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