(R)-3-Benzyloxy-3-((2S,3R,6R)-2,6-dimethyl-3-trimethylsilanyloxy-tetrahydro-pyran-2-yl)-propan-1-ol

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Chemical Name:(R)-3-Benzyloxy-3-((2S,3R,6R)-2,6-dimethyl-3-trimethylsilanyloxy-tetrahydro-pyran-2-yl)-propan-1-ol
CAS No.:524734-93-8
Molecular Formula:C₂₀H₃₄O₄Si
Molecular Weight:366.573
Hs Code.:

Synonyms:(R)-3-Benzyloxy-3-((2S,3R,6R)-2,6-dimethyl-3-trimethylsilanyloxy-tetrahydro-pyran-2-yl)-propan-1-ol

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Chemical Property of (R)-3-Benzyloxy-3-((2S,3R,6R)-2,6-dimethyl-3-trimethylsilanyloxy-tetrahydro-pyran-2-yl)-propan-1-ol

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Technology Process of (R)-3-Benzyloxy-3-((2S,3R,6R)-2,6-dimethyl-3-trimethylsilanyloxy-tetrahydro-pyran-2-yl)-propan-1-ol

There total 29 articles about (R)-3-Benzyloxy-3-((2S,3R,6R)-2,6-dimethyl-3-trimethylsilanyloxy-tetrahydro-pyran-2-yl)-propan-1-ol 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: 90.0%

: 524734-91-6
[(2S,3R,6R)-2,6-Dimethyl-2-((2R,4R)-2-phenyl-[1,3]dioxan-4-yl)-tetrahydro-pyran-3-yloxy]-trimethyl-silane

: 524734-93-8
(R)-3-Benzyloxy-3-((2S,3R,6R)-2,6-dimethyl-3-trimethylsilanyloxy-tetrahydro-pyran-2-yl)-propan-1-ol

Guidance literature:: With diisobutylaluminium hydride; In toluene; at -78 - -10 ℃; for 6.5h;
DOI:10.1021/jo034021y

Reference yield:

: 23339-26-6,56196-34-0
isopropyl 2,3-dideoxy-α-D-erythro-hex-2-enopyranoside

: 524734-93-8
(R)-3-Benzyloxy-3-((2S,3R,6R)-2,6-dimethyl-3-trimethylsilanyloxy-tetrahydro-pyran-2-yl)-propan-1-ol

Guidance literature:: Multi-step reaction with 27 steps

1.1: 100 percent / imidazole / dimethylformamide / 0.5 h / 0 °C

2.1: 97 percent / Ac₂O / dimethylsulfoxide / 11.5 h / 20 °C

3.1: n-BuLi / tetrahydrofuran / 0.5 h / 20 °C

3.2: 81 percent / tetrahydrofuran / 2.5 h / -78 - 20 °C

4.1: 79 percent / Li; liquid NH₃ / ethanol / 0.5 h / Heating

5.1: 74 percent / AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 25.5 h / 20 °C

6.1: 94 percent / pyridine / CH₂Cl₂ / 7 h / 20 °C

7.1: 86 percent / TBAF / tetrahydrofuran / 0.08 h / 0 °C

8.1: 100 percent / imidazole; PPh₃; I₂ / acetonitrile / 20 h / 20 °C

9.1: 88 percent / dimethylsulfoxide / 16.5 h / 60 °C

10.1: BF₃*OEt₂ / CH₂Cl₂ / 0.67 h / 0 °C

10.2: 78 percent / CSA / CH₂Cl₂ / 4 h / 20 °C

11.1: 77 percent / K₂CO₃ / methanol / 1.5 h / 20 °C

12.1: 100 percent / imidazole / dimethylformamide / 3.58 h / 20 °C

13.1: 83 percent / NaHCO₃; MeI / acetonitrile / 10.67 h / 20 °C

14.1: 87 percent / tetrahydrofuran / 0.33 h / -78 °C

15.1: TBAF / tetrahydrofuran / 0.5 h / 20 °C

16.1: 116 mg / pyridine; DMAP / CH₂Cl₂ / 16 h / 20 °C

17.1: 348 mg / n-Bu₃P; Et₃N; HCO₂H / Pd₂(dba)3*CHCl₃ / tetrahydrofuran / 0.5 h / 60 °C

18.1: 98 percent / H₂O; CuCl / PdCl₂ / dimethylformamide / 32 h / 20 °C

19.1: 88 percent / BF₃*OEt₂ / acetonitrile; 1,2-dichloro-ethane / 18 h / 50 °C

20.1: 100 percent / Et₃SiH; TiCl₄ / CH₂Cl₂ / 0.33 h / 0 °C

21.1: K₂CO₃ / methanol / 0.33 h / 20 °C

22.1: 102 mg / CSA / CH₂Cl₂ / 2 h / 20 °C

23.1: 95 percent / DIBAL / CH₂Cl₂; toluene / 1 h / -78 °C

24.1: 99 percent / NaBH₄ / methanol / 0.33 h / 0 °C

25.1: 86 percent / CSA / CH₂Cl₂ / 12 h / 20 °C

26.1: 97 percent / Et₃N; DMAP / CH₂Cl₂ / 0.17 h / 0 °C

27.1: 90 percent / DIBAL / toluene / 6.5 h / -78 - -10 °C

With pyridine; 1H-imidazole; triethylsilane; dmap; sodium tetrahydroborate; n-butyllithium; formic acid; tributylphosphine; methanesulfonamide; AD-mix-β; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; ammonia; water; iodine; acetic anhydride; titanium tetrachloride; lithium; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; triethylamine; triphenylphosphine; copper(l) chloride; methyl iodide; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; palladium dichloride; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol;
DOI:10.1021/jo034021y

Reference yield:

: 69247-19-4,113019-32-2,23339-23-3
isopropyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside

: 524734-93-8
(R)-3-Benzyloxy-3-((2S,3R,6R)-2,6-dimethyl-3-trimethylsilanyloxy-tetrahydro-pyran-2-yl)-propan-1-ol

Guidance literature:: Multi-step reaction with 28 steps

1.1: 116.5 g / Et₃N / methanol; H₂O / 5.5 h / 20 °C

2.1: 100 percent / imidazole / dimethylformamide / 0.5 h / 0 °C

3.1: 97 percent / Ac₂O / dimethylsulfoxide / 11.5 h / 20 °C

4.1: n-BuLi / tetrahydrofuran / 0.5 h / 20 °C

4.2: 81 percent / tetrahydrofuran / 2.5 h / -78 - 20 °C

5.1: 79 percent / Li; liquid NH₃ / ethanol / 0.5 h / Heating

6.1: 74 percent / AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 25.5 h / 20 °C

7.1: 94 percent / pyridine / CH₂Cl₂ / 7 h / 20 °C

8.1: 86 percent / TBAF / tetrahydrofuran / 0.08 h / 0 °C

9.1: 100 percent / imidazole; PPh₃; I₂ / acetonitrile / 20 h / 20 °C

10.1: 88 percent / dimethylsulfoxide / 16.5 h / 60 °C

11.1: BF₃*OEt₂ / CH₂Cl₂ / 0.67 h / 0 °C

11.2: 78 percent / CSA / CH₂Cl₂ / 4 h / 20 °C

12.1: 77 percent / K₂CO₃ / methanol / 1.5 h / 20 °C

13.1: 100 percent / imidazole / dimethylformamide / 3.58 h / 20 °C

14.1: 83 percent / NaHCO₃; MeI / acetonitrile / 10.67 h / 20 °C

15.1: 87 percent / tetrahydrofuran / 0.33 h / -78 °C

16.1: TBAF / tetrahydrofuran / 0.5 h / 20 °C

17.1: 116 mg / pyridine; DMAP / CH₂Cl₂ / 16 h / 20 °C

18.1: 348 mg / n-Bu₃P; Et₃N; HCO₂H / Pd₂(dba)3*CHCl₃ / tetrahydrofuran / 0.5 h / 60 °C

19.1: 98 percent / H₂O; CuCl / PdCl₂ / dimethylformamide / 32 h / 20 °C

20.1: 88 percent / BF₃*OEt₂ / acetonitrile; 1,2-dichloro-ethane / 18 h / 50 °C

21.1: 100 percent / Et₃SiH; TiCl₄ / CH₂Cl₂ / 0.33 h / 0 °C

22.1: K₂CO₃ / methanol / 0.33 h / 20 °C

23.1: 102 mg / CSA / CH₂Cl₂ / 2 h / 20 °C

24.1: 95 percent / DIBAL / CH₂Cl₂; toluene / 1 h / -78 °C

25.1: 99 percent / NaBH₄ / methanol / 0.33 h / 0 °C

26.1: 86 percent / CSA / CH₂Cl₂ / 12 h / 20 °C

27.1: 97 percent / Et₃N; DMAP / CH₂Cl₂ / 0.17 h / 0 °C

28.1: 90 percent / DIBAL / toluene / 6.5 h / -78 - -10 °C

With pyridine; 1H-imidazole; triethylsilane; dmap; sodium tetrahydroborate; n-butyllithium; formic acid; tributylphosphine; methanesulfonamide; AD-mix-β; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; ammonia; water; iodine; acetic anhydride; titanium tetrachloride; lithium; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; triethylamine; triphenylphosphine; copper(l) chloride; methyl iodide; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; palladium dichloride; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol;
DOI:10.1021/jo034021y