(1R,2R,4R,5S)-5-Benzyloxy-4-ethyl-1-[(2S,4S,5S)-5-((S)-1-ethyl-2-hydroxy-butyl)-2,4-dimethyl-tetrahydro-furan-2-yl]-2-methyl-heptane-1,4-diol

Base Information

Chemical Name:(1R,2R,4R,5S)-5-Benzyloxy-4-ethyl-1-[(2S,4S,5S)-5-((S)-1-ethyl-2-hydroxy-butyl)-2,4-dimethyl-tetrahydro-furan-2-yl]-2-methyl-heptane-1,4-diol
CAS No.:144535-01-3
Molecular Formula:C₂₉H₅₀O₅
Molecular Weight:478.713
Hs Code.:

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Chemical Property of (1R,2R,4R,5S)-5-Benzyloxy-4-ethyl-1-[(2S,4S,5S)-5-((S)-1-ethyl-2-hydroxy-butyl)-2,4-dimethyl-tetrahydro-furan-2-yl]-2-methyl-heptane-1,4-diol

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Technology Process of (1R,2R,4R,5S)-5-Benzyloxy-4-ethyl-1-[(2S,4S,5S)-5-((S)-1-ethyl-2-hydroxy-butyl)-2,4-dimethyl-tetrahydro-furan-2-yl]-2-methyl-heptane-1,4-diol

There total 17 articles about (1R,2R,4R,5S)-5-Benzyloxy-4-ethyl-1-[(2S,4S,5S)-5-((S)-1-ethyl-2-hydroxy-butyl)-2,4-dimethyl-tetrahydro-furan-2-yl]-2-methyl-heptane-1,4-diol 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:

: (1R,2R,4R,5S)-5-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-4-ethyl-1-[(2S,4S,5S)-5-((S)-1-ethyl-2-hydroxy-butyl)-2,4-dimethyl-tetrahydro-furan-2-yl]-2-methyl-heptan-1-ol

: 144535-01-3,144606-49-5
(1R,2R,4R,5S)-5-Benzyloxy-4-ethyl-1-[(2S,4S,5S)-5-((S)-1-ethyl-2-hydroxy-butyl)-2,4-dimethyl-tetrahydro-furan-2-yl]-2-methyl-heptane-1,4-diol

Guidance literature:: With tetrabutyl ammonium fluoride; In N,N-dimethyl-formamide; Yield given; Ambient temperature;
DOI:10.1016/S0040-4039(00)61140-1

Reference yield:

: 152934-39-9
(2S)-2-<(4S,5S)-5-Ethyl-2,2-dimethyl-1,2-dioxan-4-yl>propan-1-ol

: 144535-01-3,144606-49-5
(1R,2R,4R,5S)-5-Benzyloxy-4-ethyl-1-[(2S,4S,5S)-5-((S)-1-ethyl-2-hydroxy-butyl)-2,4-dimethyl-tetrahydro-furan-2-yl]-2-methyl-heptane-1,4-diol

Guidance literature:: Multi-step reaction with 16 steps

2: 1.) t-BuLi / 1.) ether, -78 deg C

3: Swern oxidation

4: diethyl ether / -78 to -20 deg C

5: DDQ / CH₂Cl₂; H₂O / Ambient temperature

6: LiAlH₄ / diethyl ether / 0 °C

7: pyridine / 0 °C

8: 1N H₂SO₄ / tetrahydrofuran / Ambient temperature

9: K₂CO₃ / methanol / Ambient temperature

10: CSA / CH₂Cl₂ / 0 °C

11: imidazole / CH₂Cl₂ / 0 deg C to room temp.

12: TEA, DMAP / CH₂Cl₂ / Ambient temperature

13: 1N HCl / tetrahydrofuran / Ambient temperature

14: Swern oxidation

15: tetrahydrofuran / -78 to -20 deg C

16: n-Bu₄NF / dimethylformamide / Ambient temperature

With pyridine; 1H-imidazole; hydrogenchloride; dmap; lithium aluminium tetrahydride; TEA; sulfuric acid; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; tert.-butyl lithium; potassium carbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)61140-1

Reference yield:

: 144534-92-9
(4R,5S)-5-Ethyl-4-((R)-2-iodo-1-methyl-ethyl)-2,2-dimethyl-[1,3]dioxane

: 144535-01-3,144606-49-5
(1R,2R,4R,5S)-5-Benzyloxy-4-ethyl-1-[(2S,4S,5S)-5-((S)-1-ethyl-2-hydroxy-butyl)-2,4-dimethyl-tetrahydro-furan-2-yl]-2-methyl-heptane-1,4-diol

Guidance literature:: Multi-step reaction with 15 steps

1: 1.) t-BuLi / 1.) ether, -78 deg C

2: Swern oxidation

3: diethyl ether / -78 to -20 deg C

4: DDQ / CH₂Cl₂; H₂O / Ambient temperature

5: LiAlH₄ / diethyl ether / 0 °C

6: pyridine / 0 °C

7: 1N H₂SO₄ / tetrahydrofuran / Ambient temperature

8: K₂CO₃ / methanol / Ambient temperature

9: CSA / CH₂Cl₂ / 0 °C

10: imidazole / CH₂Cl₂ / 0 deg C to room temp.

11: TEA, DMAP / CH₂Cl₂ / Ambient temperature

12: 1N HCl / tetrahydrofuran / Ambient temperature

13: Swern oxidation

14: tetrahydrofuran / -78 to -20 deg C

15: n-Bu₄NF / dimethylformamide / Ambient temperature

With pyridine; 1H-imidazole; hydrogenchloride; dmap; lithium aluminium tetrahydride; TEA; sulfuric acid; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; tert.-butyl lithium; potassium carbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)61140-1