(4R,5S,6R)-4-((S)-2-Benzyloxymethoxy-1-methyl-ethyl)-6-isopropenyl-2,2,5-trimethyl-[1,3]dioxane

Base Information

Chemical Name:(4R,5S,6R)-4-((S)-2-Benzyloxymethoxy-1-methyl-ethyl)-6-isopropenyl-2,2,5-trimethyl-[1,3]dioxane
CAS No.:86534-94-3
Molecular Formula:C₂₁H₃₂O₄
Molecular Weight:348.483
Hs Code.:

Synonyms:

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Chemical Property of (4R,5S,6R)-4-((S)-2-Benzyloxymethoxy-1-methyl-ethyl)-6-isopropenyl-2,2,5-trimethyl-[1,3]dioxane

Chemical Property:

Purity/Quality:

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Technology Process of (4R,5S,6R)-4-((S)-2-Benzyloxymethoxy-1-methyl-ethyl)-6-isopropenyl-2,2,5-trimethyl-[1,3]dioxane

There total 14 articles about (4R,5S,6R)-4-((S)-2-Benzyloxymethoxy-1-methyl-ethyl)-6-isopropenyl-2,2,5-trimethyl-[1,3]dioxane 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:

: (2S,3R,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxy-2,4-dimethyl-pentanoic acid

: 86534-94-3
(4R,5S,6R)-4-((S)-2-Benzyloxymethoxy-1-methyl-ethyl)-6-isopropenyl-2,2,5-trimethyl-[1,3]dioxane

Guidance literature:: Multi-step reaction with 12 steps

1: diethyl ether

2: (iC₃H₇)2NC₂H₅ / CH₂Cl₂

3: DIBAL / CH₂Cl₂ / -78 °C

4: 95 percent / PCC, propylene oxide / CH₂Cl₂

5: tetrahydrofuran / 10 h / -100 °C

6: LiAlH₄ / diethyl ether / 0 °C

7: (C₄H₉)4N⁽¹⁺⁾*F(-) / tetrahydrofuran

8: N(C₂H₅)3 / DMAP / CH₂Cl₂

9: pyridine*TsOH

10: (C₄H₉)4N⁽¹⁺⁾*F^(1-) / tetrahydrofuran

11: P(C₄H₉)3 / tetrahydrofuran

12: H₂O₂

With lithium aluminium tetrahydride; P(C₄H₉)3; tetrabutyl ammonium fluoride; dihydrogen peroxide; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; methyloxirane; dmap; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1016/S0040-4039(00)81643-3

Reference yield:

: (2S,3R,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-2,4-dimethyl-5-oxo-pentanoic acid

: 86534-94-3
(4R,5S,6R)-4-((S)-2-Benzyloxymethoxy-1-methyl-ethyl)-6-isopropenyl-2,2,5-trimethyl-[1,3]dioxane

Guidance literature:: Multi-step reaction with 13 steps

1: NaBH₄ / methanol; CH₂Cl₂ / 4 h / -78 - 20 °C

2: diethyl ether

3: (iC₃H₇)2NC₂H₅ / CH₂Cl₂

4: DIBAL / CH₂Cl₂ / -78 °C

5: 95 percent / PCC, propylene oxide / CH₂Cl₂

6: tetrahydrofuran / 10 h / -100 °C

7: LiAlH₄ / diethyl ether / 0 °C

8: (C₄H₉)4N⁽¹⁺⁾*F(-) / tetrahydrofuran

9: N(C₂H₅)3 / DMAP / CH₂Cl₂

10: pyridine*TsOH

11: (C₄H₉)4N⁽¹⁺⁾*F^(1-) / tetrahydrofuran

12: P(C₄H₉)3 / tetrahydrofuran

13: H₂O₂

With sodium tetrahydroborate; lithium aluminium tetrahydride; P(C₄H₉)3; tetrabutyl ammonium fluoride; dihydrogen peroxide; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; methyloxirane; dmap; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;
DOI:10.1016/S0040-4039(00)81643-3

Reference yield:

: 82281-55-8
(3S,4R,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethyl-1-trimethylsilanyloxy-cyclopentene

: 86534-94-3
(4R,5S,6R)-4-((S)-2-Benzyloxymethoxy-1-methyl-ethyl)-6-isopropenyl-2,2,5-trimethyl-[1,3]dioxane

Guidance literature:: Multi-step reaction with 14 steps

1: ozone / methanol; CH₂Cl₂ / -78 °C

2: NaBH₄ / methanol; CH₂Cl₂ / 4 h / -78 - 20 °C

3: diethyl ether

4: (iC₃H₇)2NC₂H₅ / CH₂Cl₂

5: DIBAL / CH₂Cl₂ / -78 °C

6: 95 percent / PCC, propylene oxide / CH₂Cl₂

7: tetrahydrofuran / 10 h / -100 °C

8: LiAlH₄ / diethyl ether / 0 °C

9: (C₄H₉)4N⁽¹⁺⁾*F(-) / tetrahydrofuran

10: N(C₂H₅)3 / DMAP / CH₂Cl₂

11: pyridine*TsOH

12: (C₄H₉)4N⁽¹⁺⁾*F^(1-) / tetrahydrofuran

13: P(C₄H₉)3 / tetrahydrofuran

14: H₂O₂

With sodium tetrahydroborate; lithium aluminium tetrahydride; P(C₄H₉)3; tetrabutyl ammonium fluoride; dihydrogen peroxide; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; methyloxirane; dmap; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;
DOI:10.1016/S0040-4039(00)81643-3