(2R,4S,5R,6R)-4,5-Bis-benzyloxy-6-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-dihydro-pyran-3-one

Base Information

• Chemical Name: (2R,4S,5R,6R)-4,5-Bis-benzyloxy-6-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-dihydro-pyran-3-one
• CAS No.: 1053633-86-5
• Molecular Formula: C₇₅H₇₄O₁₁
• Molecular Weight: 1151.41

Synonyms:(2R,4S,5R,6R)-4,5-Bis-benzyloxy-6-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-dihydro-pyran-3-one

Chemical Property of (2R,4S,5R,6R)-4,5-Bis-benzyloxy-6-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-dihydro-pyran-3-one

Chemical Property:

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Technology Process of (2R,4S,5R,6R)-4,5-Bis-benzyloxy-6-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-dihydro-pyran-3-one

There total 22 articles about (2R,4S,5R,6R)-4,5-Bis-benzyloxy-6-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-dihydro-pyran-3-one 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) → (2R,4S,5R,6R)-4,5-Bis-benzyloxy-6-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-dihydro-pyran-3-one (1053633-86-5)

Guidance literature:

Multi-step reaction with 16 steps

2: 3-Angstroem molecular sieves, NaHCO₃, Dess-Martin periodinane / CH₂Cl₂ / 1.5 h

3: 0.02percent NiCl₂ in CrCl₂ / tetrahydrofuran; dimethylformamide / 12 h / Ambient temperature

4: 89 percent / H₂ / 10percent Pd-Pb/CaCO₃ / methanol / 12 h / 760 Torr / Ambient temperature

5: 88 percent / NaH, imidazole, (n-Bu)4NI / tetrahydrofuran; dimethylformamide / 1.) room temp., 15 min, 2.) 6 h

6: 91 percent / OsO₄ / tetrahydrofuran; pyridine; toluene / 48 h / -35 °C

7: 1.) Bu₂SnO, 2.) CsF, (n-Bu)4NI / 1.) toluene, reflux, 2 h, 2.) DMF, room temp., 36 h

8: 95 percent / pyridine, 4-(dimethylamino)pyridine / 0.5 h

9: 95 percent / 80percent aq. AcOH / 12 h / Ambient temperature

10: pyridine / 9 h

11: NaH, imidazole / tetrahydrofuran / 0.33 h / 0 °C

12: DDQ / CH₂Cl₂ / 2 h / 0 °C / pH 7 phosphate buffer

13: p-TsOH*H₂O / CH₂Cl₂ / 0.83 h

14: 90 percent / pyridine / 6 h / 50 °C

15: 95 percent / K₂CO₃ / methanol / 3 h / Ambient temperature

16: Swern oxidation

With pyridine; 1H-imidazole; dmap; osmium(VIII) oxide; 3 A molecular sieve; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; acetic acid; cesium fluoride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; nickel dichloride; Lindlar's catalyst; palladium-lead; In tetrahydrofuran; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo00080a016

Reference yield:

2-O-benzyl-3,4-O-isopropylidene-L-threitol (84379-53-3) → (2R,4S,5R,6R)-4,5-Bis-benzyloxy-6-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-dihydro-pyran-3-one (1053633-86-5)

Guidance literature:

Multi-step reaction with 15 steps

1: 3-Angstroem molecular sieves, NaHCO₃, Dess-Martin periodinane / CH₂Cl₂ / 1.5 h

2: 0.02percent NiCl₂ in CrCl₂ / tetrahydrofuran; dimethylformamide / 12 h / Ambient temperature

3: 89 percent / H₂ / 10percent Pd-Pb/CaCO₃ / methanol / 12 h / 760 Torr / Ambient temperature

4: 88 percent / NaH, imidazole, (n-Bu)4NI / tetrahydrofuran; dimethylformamide / 1.) room temp., 15 min, 2.) 6 h

5: 91 percent / OsO₄ / tetrahydrofuran; pyridine; toluene / 48 h / -35 °C

6: 1.) Bu₂SnO, 2.) CsF, (n-Bu)4NI / 1.) toluene, reflux, 2 h, 2.) DMF, room temp., 36 h

7: 95 percent / pyridine, 4-(dimethylamino)pyridine / 0.5 h

8: 95 percent / 80percent aq. AcOH / 12 h / Ambient temperature

9: pyridine / 9 h

10: NaH, imidazole / tetrahydrofuran / 0.33 h / 0 °C

11: DDQ / CH₂Cl₂ / 2 h / 0 °C / pH 7 phosphate buffer

12: p-TsOH*H₂O / CH₂Cl₂ / 0.83 h

13: 90 percent / pyridine / 6 h / 50 °C

14: 95 percent / K₂CO₃ / methanol / 3 h / Ambient temperature

15: Swern oxidation

With pyridine; 1H-imidazole; dmap; osmium(VIII) oxide; 3 A molecular sieve; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; acetic acid; cesium fluoride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; nickel dichloride; Lindlar's catalyst; palladium-lead; In tetrahydrofuran; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo00080a016

Reference yield:

2-O-benzyl-3,4-O-isopropylidene-L-threose (100906-42-1) → (2R,4S,5R,6R)-4,5-Bis-benzyloxy-6-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-dihydro-pyran-3-one (1053633-86-5)

Guidance literature:

Multi-step reaction with 14 steps

1: 0.02percent NiCl₂ in CrCl₂ / tetrahydrofuran; dimethylformamide / 12 h / Ambient temperature

2: 89 percent / H₂ / 10percent Pd-Pb/CaCO₃ / methanol / 12 h / 760 Torr / Ambient temperature

3: 88 percent / NaH, imidazole, (n-Bu)4NI / tetrahydrofuran; dimethylformamide / 1.) room temp., 15 min, 2.) 6 h

4: 91 percent / OsO₄ / tetrahydrofuran; pyridine; toluene / 48 h / -35 °C

5: 1.) Bu₂SnO, 2.) CsF, (n-Bu)4NI / 1.) toluene, reflux, 2 h, 2.) DMF, room temp., 36 h

6: 95 percent / pyridine, 4-(dimethylamino)pyridine / 0.5 h

7: 95 percent / 80percent aq. AcOH / 12 h / Ambient temperature

8: pyridine / 9 h

9: NaH, imidazole / tetrahydrofuran / 0.33 h / 0 °C

10: DDQ / CH₂Cl₂ / 2 h / 0 °C / pH 7 phosphate buffer

11: p-TsOH*H₂O / CH₂Cl₂ / 0.83 h

12: 90 percent / pyridine / 6 h / 50 °C

13: 95 percent / K₂CO₃ / methanol / 3 h / Ambient temperature

14: Swern oxidation

With pyridine; 1H-imidazole; dmap; osmium(VIII) oxide; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; potassium carbonate; toluene-4-sulfonic acid; acetic acid; cesium fluoride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; nickel dichloride; Lindlar's catalyst; palladium-lead; In tetrahydrofuran; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo00080a016

upstream raw materials:

benzyl bromide

2-O-benzyl-3,4-O-isopropylidene-L-threitol

2-O-benzyl-3,4-O-isopropylidene-L-threose

1-(2,3,4,6-O-tetrabenzyl-α-D-glucopyranosyl)-2-propene

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