(R)-benzyl 2-((2R,5S)-5-((S)-2-hydroxypropyl)tetrahydrofuran-2-yl)propanoate

Base Information

Chemical Name:(R)-benzyl 2-((2R,5S)-5-((S)-2-hydroxypropyl)tetrahydrofuran-2-yl)propanoate
CAS No.:58106-10-8
Molecular Formula:C₁₇H₂₄O₄
Molecular Weight:292.375
Hs Code.:

Synonyms:(R)-benzyl 2-((2R,5S)-5-((S)-2-hydroxypropyl)tetrahydrofuran-2-yl)propanoate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (R)-benzyl 2-((2R,5S)-5-((S)-2-hydroxypropyl)tetrahydrofuran-2-yl)propanoate

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Technology Process of (R)-benzyl 2-((2R,5S)-5-((S)-2-hydroxypropyl)tetrahydrofuran-2-yl)propanoate

There total 28 articles about (R)-benzyl 2-((2R,5S)-5-((S)-2-hydroxypropyl)tetrahydrofuran-2-yl)propanoate 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: 87.0%

: 100-39-0
benzyl bromide

: 16221-11-7
acide (-) nonactique

: 58106-10-8
(R)-benzyl 2-((2R,5S)-5-((S)-2-hydroxypropyl)tetrahydrofuran-2-yl)propanoate

Guidance literature:: With potassium tert-butylate; In N,N-dimethyl-formamide; at 60 ℃; for 20h;
DOI:10.1021/ol0609661

Reference yield: 78.0%

: 215110-76-2
(2S,3R,6R,8S)-8-(tert-Butyl-dimethyl-silanyloxy)-3-(dimethyl-p-tolyl-silanyl)-2-methyl-6-(toluene-4-sulfonyloxy)-nonanoic acid benzyl ester

: 58106-10-8
(R)-benzyl 2-((2R,5S)-5-((S)-2-hydroxypropyl)tetrahydrofuran-2-yl)propanoate

Guidance literature:: With peracetic acid; potassium bromide; In acetic acid; for 15h; Ambient temperature;

Reference yield:

: 159276-72-9
(4S,5S)-4-(Dimethyl-p-tolyl-silanyl)-5-[(1S,2S)-1-(dimethyl-p-tolyl-silanyl)-2-hydroxy-3-(2-methyl-[1,3]dioxolan-2-yl)-propyl]-dihydro-furan-2-one

: 58106-10-8
(R)-benzyl 2-((2R,5S)-5-((S)-2-hydroxypropyl)tetrahydrofuran-2-yl)propanoate

Guidance literature:: Multi-step reaction with 14 steps

1: KH / tetrahydrofuran / 1.) -78 to -20 deg C, 2 h; -5 deg C, 1 h, 2.) 0 deg C, 1 h

2: H₂ / PtO₂ / methanol / 50 h / Ambient temperature

3: diethyl ether

4: 93 percent / pyridinium toluene p-sulfonate / acetone; H₂O / 2.5 h / Heating

5: 1.) Bu₂BOMe, 2.) NaBH₄ / 1.) THF, MeOH, -78 deg C, 20 min, 2.) THF, MeOH, -78 deg C, 15 h

6: 96 percent / p-TsOH*pyridine / 15 h / Ambient temperature

7: 93 percent / LDA, DMPU / hexane; tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -78 deg C, 46 h; -78 to -10 deg C, 8 h

8: TsOH*pyridine / methanol / 2.5 h

9: KOH, H₂O / methanol; tetrahydrofuran / 15 h / 40 °C

10: 86 percent / Et₃N, 2-chloro-1-methylpyridinium iodide / CH₂Cl₂ / 1 h / Heating

11: 90 percent / imidazole / dimethylformamide / 15 h / Ambient temperature

12: 97 percent / NaOBn / tetrahydrofuran / 6 h / Ambient temperature

13: 97 percent / DMAP, pyridine / 48 h / Ambient temperature

14: 78 percent / AcO₂H, KBr / acetic acid / 15 h / Ambient temperature

With pyridine; 1H-imidazole; peracetic acid; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; potassium hydroxide; sodium tetrahydroborate; dibutylborinic acid methyl ester; 2-chloro-1-methyl-pyridinium iodide; water; hydrogen; pyridinium p-toluenesulfonate; potassium hydride; triethylamine; sodium phenyl-methanolate; potassium bromide; lithium diisopropyl amide; platinum(IV) oxide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; acetone;