1,3-Dioxane-4-acetic acid, 2,2-dimethyl-6-[(2R)-4-oxo-2-(phenylmethoxy)pentyl]-, methyl ester, (4R,6R)-

Base Information

Chemical Name:1,3-Dioxane-4-acetic acid, 2,2-dimethyl-6-[(2R)-4-oxo-2-(phenylmethoxy)pentyl]-, methyl ester, (4R,6R)-
CAS No.:500533-15-3
Molecular Formula:C21H30O6
Molecular Weight:378.466
Hs Code.:

Synonyms:

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Chemical Property of 1,3-Dioxane-4-acetic acid, 2,2-dimethyl-6-[(2R)-4-oxo-2-(phenylmethoxy)pentyl]-, methyl ester, (4R,6R)-

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Technology Process of 1,3-Dioxane-4-acetic acid, 2,2-dimethyl-6-[(2R)-4-oxo-2-(phenylmethoxy)pentyl]-, methyl ester, (4R,6R)-

There total 1 articles about 1,3-Dioxane-4-acetic acid, 2,2-dimethyl-6-[(2R)-4-oxo-2-(phenylmethoxy)pentyl]-, methyl ester, (4R,6R)- 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: 73.0%

: 251908-60-8
(2''S,4R,6R)-6-(2''-Benzyloxy-4''-pentenyl)-4-(methoxycarbonylmethyl)-2,2-dimethyl-1,3-dioxane

: 500533-15-3
[(4R,6R)-6-((R)-2-Benzyloxy-4-oxo-pentyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-acetic acid methyl ester

Guidance literature:: With water; palladium dichloride; In N,N-dimethyl-formamide; at 70 ℃;
DOI:10.1055/s-2002-35584

Reference yield: 65.0%

: 500533-15-3
[(4R,6R)-6-((R)-2-Benzyloxy-4-oxo-pentyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-acetic acid methyl ester

: 500533-16-4
(S)-3-Benzyloxy-4-{(4R,6S)-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-butyraldehyde

: [(4R,6R)-6-((2R,8R)-2,8-Bis-benzyloxy-9-{(4R,6S)-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-6-hydroxy-4-oxo-nonyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-acetic acid methyl ester

Guidance literature:: [(4R,6R)-6-((R)-2-Benzyloxy-4-oxo-pentyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-acetic acid methyl ester; With di-n-butylboryl trifluoromethanesulfonate; triethylamine; In dichloromethane; at -78 - 0 ℃; for 1h;

(S)-3-Benzyloxy-4-{(4R,6S)-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-butyraldehyde; In diethyl ether; dichloromethane; at -100 - -78 ℃; for 6h;
DOI:10.1055/s-2002-35584

Reference yield:

: 500533-15-3
[(4R,6R)-6-((R)-2-Benzyloxy-4-oxo-pentyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-acetic acid methyl ester

: 500533-20-0
tert-Butyl-{2-[(4S,6S)-6-((4R,6R)-6-{(4R,6S)-6-[(4R,6R)-6-(2,2-diphenyl-vinyl)-2,2-dimethyl-[1,3]dioxan-4-ylmethyl]-2,2-dimethyl-[1,3]dioxan-4-ylmethyl}-2,2-dimethyl-[1,3]dioxan-4-ylmethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethoxy}-dimethyl-silane

Guidance literature:: Multi-step reaction with 6 steps

1.1: Bu₂BOTf; Et₃N / CH₂Cl₂ / 1 h / -78 - 0 °C

1.2: 65 percent / CH₂Cl₂; diethyl ether / 6 h / -100 - -78 °C

2.1: 93 percent / (Me₄N)BH(OAc)3; AcOH / acetonitrile / -20 °C

3.1: HCOONH₄ / Pd/C / methanol / 64 °C

4.1: PPTS / CH₂Cl₂ / 20 °C

5.1: tetrahydrofuran / 0 °C

6.1: MeO₂CNSO₂NEt₃ / toluene / 55 °C

With Burgess Reagent; di-n-butylboryl trifluoromethanesulfonate; ammonium formate; pyridinium p-toluenesulfonate; acetic acid; triethylamine; tetramethylammonium triacetoxyborohydride; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; toluene; acetonitrile; 6.1: Burgess elimination;
DOI:10.1055/s-2002-35584