(3R,5R)-5-((R)-3-Benzyloxy-1-triisopropylsilanyloxy-propyl)-3-methyl-dihydro-furan-2-one

Base Information

Chemical Name:(3R,5R)-5-((R)-3-Benzyloxy-1-triisopropylsilanyloxy-propyl)-3-methyl-dihydro-furan-2-one
CAS No.:795306-62-6
Molecular Formula:C₂₄H₄₀O₄Si
Molecular Weight:420.665
Hs Code.:

Synonyms:(3R,5R)-5-((R)-3-Benzyloxy-1-triisopropylsilanyloxy-propyl)-3-methyl-dihydro-furan-2-one

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Chemical Property of (3R,5R)-5-((R)-3-Benzyloxy-1-triisopropylsilanyloxy-propyl)-3-methyl-dihydro-furan-2-one

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Technology Process of (3R,5R)-5-((R)-3-Benzyloxy-1-triisopropylsilanyloxy-propyl)-3-methyl-dihydro-furan-2-one

There total 9 articles about (3R,5R)-5-((R)-3-Benzyloxy-1-triisopropylsilanyloxy-propyl)-3-methyl-dihydro-furan-2-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: 88.0%

: (R)-5-(3-Benzyloxy-1-hydroxy-propyl)-3-methyl-dihydro-furan-2-one

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 795306-62-6
(3R,5R)-5-((R)-3-Benzyloxy-1-triisopropylsilanyloxy-propyl)-3-methyl-dihydro-furan-2-one

Guidance literature:: With 1H-imidazole; dmap; In N,N-dimethyl-formamide; at 20 ℃; for 18h;
DOI:10.1039/b410092a

Reference yield:

: 795306-29-5
(S)-4-Benzyl-3-((E)-(R)-7-benzyloxy-2-methyl-hept-4-enoyl)-oxazolidin-2-one

: 795306-62-6
(3R,5R)-5-((R)-3-Benzyloxy-1-triisopropylsilanyloxy-propyl)-3-methyl-dihydro-furan-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: 55 percent / AD mix β; aq. NaHCO3 / 2-methyl-propan-2-ol / 18 h / 20 °C

2: 88 percent / imidazole; DMAP / dimethylformamide / 18 h / 20 °C

With 1H-imidazole; dmap; sodium hydrogencarbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; In N,N-dimethyl-formamide; tert-butyl alcohol; 1: Sharpless dihydroxylation;
DOI:10.1039/b410092a

Reference yield:

: 4799-68-2
3-benzyloxypropan-1-ol

: 795306-62-6
(3R,5R)-5-((R)-3-Benzyloxy-1-triisopropylsilanyloxy-propyl)-3-methyl-dihydro-furan-2-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1.42 h / -50 - 20 °C

2.1: 11.28 g / CH₂Cl₂

3.1: 81 percent / DIBAL-H / CH₂Cl₂ / 1 h / -78 °C

4.1: 70 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

5.1: 78 percent / NaI / dimethylformamide / 1 h / 20 °C

6.1: NaHMDS / tetrahydrofuran / 0.33 h / -78 °C

6.2: 92 percent / tetrahydrofuran / 1 h / -78 °C

7.1: 55 percent / AD mix β; aq. NaHCO3 / 2-methyl-propan-2-ol / 18 h / 20 °C

8.1: 88 percent / imidazole; DMAP / dimethylformamide / 18 h / 20 °C

With 1H-imidazole; dmap; oxalyl dichloride; sodium hexamethyldisilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; sodium iodide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; 7.1: Sharpless dihydroxylation;
DOI:10.1039/b410092a