(2S,3R,4R,5R,6R)-4-hydroxy-2-methoxy-6-methyl-3-phenylcarbonyloxy-5-tert-butyldimethylsilyloxytetrahydro-2H-pyran

Base Information

Chemical Name:(2S,3R,4R,5R,6R)-4-hydroxy-2-methoxy-6-methyl-3-phenylcarbonyloxy-5-tert-butyldimethylsilyloxytetrahydro-2H-pyran
CAS No.:876133-10-7
Molecular Formula:C₂₀H₃₂O₆Si
Molecular Weight:396.556
Hs Code.:

Synonyms:(2S,3R,4R,5R,6R)-4-hydroxy-2-methoxy-6-methyl-3-phenylcarbonyloxy-5-tert-butyldimethylsilyloxytetrahydro-2H-pyran

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Chemical Property of (2S,3R,4R,5R,6R)-4-hydroxy-2-methoxy-6-methyl-3-phenylcarbonyloxy-5-tert-butyldimethylsilyloxytetrahydro-2H-pyran

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Technology Process of (2S,3R,4R,5R,6R)-4-hydroxy-2-methoxy-6-methyl-3-phenylcarbonyloxy-5-tert-butyldimethylsilyloxytetrahydro-2H-pyran

There total 10 articles about (2S,3R,4R,5R,6R)-4-hydroxy-2-methoxy-6-methyl-3-phenylcarbonyloxy-5-tert-butyldimethylsilyloxytetrahydro-2H-pyran 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: 95.0%

: 876133-16-3
(2S,3R,4R,5R,6R)-5-tert-butyldimethylsilyloxy-2-methoxy-6-methyl-4-(3-oxobutylcarbonyloxy)-3-phenylcarbonyloxytetrahydro-2H-pyran

: 876133-10-7
(2S,3R,4R,5R,6R)-4-hydroxy-2-methoxy-6-methyl-3-phenylcarbonyloxy-5-tert-butyldimethylsilyloxytetrahydro-2H-pyran

Guidance literature:: With pyridine; hydrazine hydrate; acetic acid; at 20 ℃; for 24h;
DOI:10.1055/s-2005-918474

Reference yield:

: 876133-06-1
(2R,4aR,6S,7R,8R,8aR)-6-methoxy-8-(3-oxobutylcarbonyloxy)-2-phenyl-7-phenylcarbonyloxyperhydropyrano[3,2-d][1,3]dioxine

: 876133-10-7
(2S,3R,4R,5R,6R)-4-hydroxy-2-methoxy-6-methyl-3-phenylcarbonyloxy-5-tert-butyldimethylsilyloxytetrahydro-2H-pyran

Guidance literature:: Multi-step reaction with 5 steps

1: H₂ / Pd/C / ethyl acetate / 12 h / 20 °C

2: 53.00 g / PPh₃; I₂; imidazole / tetrahydrofuran / 1 h / 20 °C

3: 95 percent / imidazole / CH₂Cl₂ / 50 h / 20 °C

4: 95 percent / 2,2'-azobis(isobutyronitrile); Bu₃SnH / toluene / 2.5 h / Heating

5: 95 percent / hydrazine monohydrate; pyridine; AcOH / 24 h / 20 °C

With pyridine; 1H-imidazole; 2,2'-azobis(isobutyronitrile); hydrogen; iodine; tri-n-butyl-tin hydride; hydrazine hydrate; acetic acid; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene;
DOI:10.1055/s-2005-918474

Reference yield:

: 99265-94-8
(2R,4aR,6S,7R,8R,8aR)-8-hydroxy-6-methoxy-2-phenyl-7-phenylcarbonyloxyperhydropyrano[3,2-d][1,3]dioxine

: 876133-10-7
(2S,3R,4R,5R,6R)-4-hydroxy-2-methoxy-6-methyl-3-phenylcarbonyloxy-5-tert-butyldimethylsilyloxytetrahydro-2H-pyran

Guidance literature:: Multi-step reaction with 6 steps

1: 143.0 g / dicyclohexylcarbodiimide; DMAP / CH₂Cl₂ / 17 h / 20 °C

2: H₂ / Pd/C / ethyl acetate / 12 h / 20 °C

3: 53.00 g / PPh₃; I₂; imidazole / tetrahydrofuran / 1 h / 20 °C

4: 95 percent / imidazole / CH₂Cl₂ / 50 h / 20 °C

5: 95 percent / 2,2'-azobis(isobutyronitrile); Bu₃SnH / toluene / 2.5 h / Heating

6: 95 percent / hydrazine monohydrate; pyridine; AcOH / 24 h / 20 °C

With pyridine; 1H-imidazole; dmap; 2,2'-azobis(isobutyronitrile); hydrogen; iodine; tri-n-butyl-tin hydride; hydrazine hydrate; acetic acid; dicyclohexyl-carbodiimide; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene;
DOI:10.1055/s-2005-918474