(6-{5-[6-(2-benzyloxy-6-methyl-hept-3-enyl)-3-methyl-tetrahydro-pyran-2-yl]-4-hydroxy-2-oxo-pentyl}-2,2-dimethyl-[1,3]-dioxan-4-yl)acetic acid tert-butyl ester

Base Information

Chemical Name:(6-{5-[6-(2-benzyloxy-6-methyl-hept-3-enyl)-3-methyl-tetrahydro-pyran-2-yl]-4-hydroxy-2-oxo-pentyl}-2,2-dimethyl-[1,3]-dioxan-4-yl)acetic acid tert-butyl ester
CAS No.:623566-61-0
Molecular Formula:C₃₈H₆₀O₈
Molecular Weight:644.89
Hs Code.:

(6-{5-[6-(2-benzyloxy-6-methyl-hept-3-enyl)-3-methyl-tetrahydro-pyran-2-yl]-4-hydroxy-2-oxo-pentyl}-2,2-dimethyl-[1,3]-dioxan-4-yl)acetic acid tert-butyl ester

Synonyms:(6-{5-[6-(2-benzyloxy-6-methyl-hept-3-enyl)-3-methyl-tetrahydro-pyran-2-yl]-4-hydroxy-2-oxo-pentyl}-2,2-dimethyl-[1,3]-dioxan-4-yl)acetic acid tert-butyl ester

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Chemical Property of (6-{5-[6-(2-benzyloxy-6-methyl-hept-3-enyl)-3-methyl-tetrahydro-pyran-2-yl]-4-hydroxy-2-oxo-pentyl}-2,2-dimethyl-[1,3]-dioxan-4-yl)acetic acid tert-butyl ester

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Technology Process of (6-{5-[6-(2-benzyloxy-6-methyl-hept-3-enyl)-3-methyl-tetrahydro-pyran-2-yl]-4-hydroxy-2-oxo-pentyl}-2,2-dimethyl-[1,3]-dioxan-4-yl)acetic acid tert-butyl ester

There total 19 articles about (6-{5-[6-(2-benzyloxy-6-methyl-hept-3-enyl)-3-methyl-tetrahydro-pyran-2-yl]-4-hydroxy-2-oxo-pentyl}-2,2-dimethyl-[1,3]-dioxan-4-yl)acetic acid tert-butyl ester 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: 81.0%

: 623566-46-1
{2,2-dimethyl-6-[2-(trimethylsilanyloxy)-allyl]-(1S,3R)-dioxan-4-yl}acetic acid tert-butyl ester

: 623566-45-0
[(2R,3S,6S)-6-((2R)-2-benzyloxy-6-methylhept-3-enyl)-3-methyltetrahydropyran-2-yl]acetaldehyde

: 623566-61-0
(6-{5-[6-(2-benzyloxy-6-methyl-hept-3-enyl)-3-methyl-tetrahydro-pyran-2-yl]-4-hydroxy-2-oxo-pentyl}-2,2-dimethyl-[1,3]-dioxan-4-yl)acetic acid tert-butyl ester

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 1.5h;
DOI:10.1021/ol035581m

Reference yield:

: methyl (2R,3S)-(E)-3-(dimethyl(phenyl)silyl)-2-(trimethylsilyloxy)-hex-4-enoate

: 623566-61-0
(6-{5-[6-(2-benzyloxy-6-methyl-hept-3-enyl)-3-methyl-tetrahydro-pyran-2-yl]-4-hydroxy-2-oxo-pentyl}-2,2-dimethyl-[1,3]-dioxan-4-yl)acetic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 13 steps

1.1: 95 percent / TMSOTf / CH₂Cl₂ / 4 h / -50 °C

2.1: 99 percent / H₂ / Pd/C / ethyl acetate / 18 h / 20 °C / 760 Torr

3.1: 76 percent / aq. CH₃CO₃H; Hg(OAc)2 / 1 h / 20 °C

4.1: 99 percent / imidazole / dimethylformamide / 12 h / 0 - 20 °C

5.1: 90 percent / Dibal-H / CH₂Cl₂; hexane / 2.5 h / 0 °C

6.1: 86 percent / (PhO)3P⁺CH₃I^- / CDCl₃ / 1 h / 0 °C

7.1: t-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; pentane / 0.33 h / -78 °C

7.2: 97 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; pentane / 2 h / -78 - 0 °C

8.1: 91 percent / Dess-Martin periodinane / methanol; H₂O; tetrahydrofuran / 20 °C

9.1: 80 percent / (S)-Corey's chiral borane; BH₃*SMe₂ / tetrahydrofuran / 8 h / -20 °C

10.1: 90 percent / n-Bu₄NI / dimethylformamide

11.1: 99 percent / TBAF / tetrahydrofuran / 20 °C

12.1: 80 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 1 h / 20 °C

13.1: 81 percent / BF₃*OEt₂ / CH₂Cl₂ / 1.5 h / -78 °C

With pyridine; 1H-imidazole; peracetic acid; trimethylsilyl trifluoromethanesulfonate; dimethylsulfide borane complex; (S)-Corey's chiral borane; boron trifluoride diethyl etherate; mercury(II) diacetate; tetrabutyl ammonium fluoride; methyltriphenoxyphosphonium iodide; hydrogen; tert.-butyl lithium; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; Dess-Martin periodane; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; chloroform-d1; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; pentane;
DOI:10.1021/ol035581m

Reference yield:

: 623566-47-2
(2S,5S,6S)-6-[2-(dimethylphenylsilyl)vinyl]-5-methyl-5,6-dihydro-2H-pyran-2-carboxylic acid methyl ester

: 623566-61-0
(6-{5-[6-(2-benzyloxy-6-methyl-hept-3-enyl)-3-methyl-tetrahydro-pyran-2-yl]-4-hydroxy-2-oxo-pentyl}-2,2-dimethyl-[1,3]-dioxan-4-yl)acetic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 12 steps

1.1: 99 percent / H₂ / Pd/C / ethyl acetate / 18 h / 20 °C / 760 Torr

2.1: 76 percent / aq. CH₃CO₃H; Hg(OAc)2 / 1 h / 20 °C

3.1: 99 percent / imidazole / dimethylformamide / 12 h / 0 - 20 °C

4.1: 90 percent / Dibal-H / CH₂Cl₂; hexane / 2.5 h / 0 °C

5.1: 86 percent / (PhO)3P⁺CH₃I^- / CDCl₃ / 1 h / 0 °C

6.1: t-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; pentane / 0.33 h / -78 °C

6.2: 97 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; pentane / 2 h / -78 - 0 °C

7.1: 91 percent / Dess-Martin periodinane / methanol; H₂O; tetrahydrofuran / 20 °C

8.1: 80 percent / (S)-Corey's chiral borane; BH₃*SMe₂ / tetrahydrofuran / 8 h / -20 °C

9.1: 90 percent / n-Bu₄NI / dimethylformamide

10.1: 99 percent / TBAF / tetrahydrofuran / 20 °C

11.1: 80 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 1 h / 20 °C

12.1: 81 percent / BF₃*OEt₂ / CH₂Cl₂ / 1.5 h / -78 °C

With pyridine; 1H-imidazole; peracetic acid; dimethylsulfide borane complex; (S)-Corey's chiral borane; boron trifluoride diethyl etherate; mercury(II) diacetate; tetrabutyl ammonium fluoride; methyltriphenoxyphosphonium iodide; hydrogen; tert.-butyl lithium; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; Dess-Martin periodane; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; chloroform-d1; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; pentane;
DOI:10.1021/ol035581m