(1'R,3'R)-5-{1',3'-Dihydroxy-3'-[furan-2''(5''H)-on-4''-yl]propyl}-5-p-methoxybenzyloxymethyl-2,2-dimethyl-1,3-dioxane

Base Information

Chemical Name:(1'R,3'R)-5-{1',3'-Dihydroxy-3'-[furan-2''(5''H)-on-4''-yl]propyl}-5-p-methoxybenzyloxymethyl-2,2-dimethyl-1,3-dioxane
CAS No.:239089-40-8
Molecular Formula:C₂₂H₃₀O₈
Molecular Weight:422.475
Hs Code.:

Synonyms:(1'R,3'R)-5-{1',3'-Dihydroxy-3'-[furan-2''(5''H)-on-4''-yl]propyl}-5-p-methoxybenzyloxymethyl-2,2-dimethyl-1,3-dioxane

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Chemical Property of (1'R,3'R)-5-{1',3'-Dihydroxy-3'-[furan-2''(5''H)-on-4''-yl]propyl}-5-p-methoxybenzyloxymethyl-2,2-dimethyl-1,3-dioxane

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Technology Process of (1'R,3'R)-5-{1',3'-Dihydroxy-3'-[furan-2''(5''H)-on-4''-yl]propyl}-5-p-methoxybenzyloxymethyl-2,2-dimethyl-1,3-dioxane

There total 12 articles about (1'R,3'R)-5-{1',3'-Dihydroxy-3'-[furan-2''(5''H)-on-4''-yl]propyl}-5-p-methoxybenzyloxymethyl-2,2-dimethyl-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:

: 4-{3-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-3-[5-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-[1,3]dioxan-5-yl]-propyl}-5H-furan-2-one

: 239089-32-8
(1'R,3'S)-5-{1',3'-Dihydroxy-3'-[furan-2''(5''H)-on-4''-yl]propyl}-5-p-methoxybenzyloxymethyl-2,2-dimethyl-1,3-dioxane

: 239089-40-8
(1'R,3'R)-5-{1',3'-Dihydroxy-3'-[furan-2''(5''H)-on-4''-yl]propyl}-5-p-methoxybenzyloxymethyl-2,2-dimethyl-1,3-dioxane

Guidance literature:: With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 25 ℃; for 2h;
DOI:10.1016/S0040-4039(99)00755-8

Reference yield:

: 3-[5-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-[1,3]dioxan-5-yl]-1-(5-triisopropylsilanyloxy-furan-3-yl)-3-trimethylsilanyloxy-propan-1-ol

: 239089-32-8
(1'R,3'S)-5-{1',3'-Dihydroxy-3'-[furan-2''(5''H)-on-4''-yl]propyl}-5-p-methoxybenzyloxymethyl-2,2-dimethyl-1,3-dioxane

: 239089-40-8
(1'R,3'R)-5-{1',3'-Dihydroxy-3'-[furan-2''(5''H)-on-4''-yl]propyl}-5-p-methoxybenzyloxymethyl-2,2-dimethyl-1,3-dioxane

: (1'S,3'S)-5-{1',3'-Dihydroxy-3'-[furan-2''(5''H)-on-4''-yl]propyl}-5-p-methoxybenzyloxymethyl-2,2-dimethyl-1,3-dioxane

: (1'S,3'R)-5-{1',3'-Dihydroxy-3'-[furan-2''(5''H)-on-4''-yl]propyl}-5-p-methoxybenzyloxymethyl-2,2-dimethyl-1,3-dioxane

Guidance literature:: With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 0 ℃; for 0.5h; Title compound not separated from byproducts;
DOI:10.1055/s-2000-8224

Reference yield:

: 770-74-1
2,2-dimethyl-5,5-bis(hydroxymethyl)-1,3-dioxane

: 239089-40-8
(1'R,3'R)-5-{1',3'-Dihydroxy-3'-[furan-2''(5''H)-on-4''-yl]propyl}-5-p-methoxybenzyloxymethyl-2,2-dimethyl-1,3-dioxane

Guidance literature:: Multi-step reaction with 9 steps

1.1: NaH / dimethylformamide / 1 h / 25 °C

2.1: 20 percent / DDQ; water / CH₂Cl₂ / 0.5 h / 25 °C

3.1: 55 percent / DIBAL-H / CH₂Cl₂ / 25 °C

4.1: 96 percent / Dess Martin periodinane / CH₂Cl₂ / 6 h / 25 °C

5.1: (+)-DIPCl / diethyl ether / 1 h / -98 °C

6.1: 94 percent / Et₂N / CH₂Cl₂ / 0.5 h / 25 °C

7.1: OsO₄; NMO / tetrahydrofuran; H₂O / 6 h / 25 °C

7.2: 100 percent / NaIO₄ / methanol; H₂O / 0.25 h / 0 °C

8.1: BuLi; TMSCl / diethyl ether / 2 h / -78 °C

9.1: Bu₄NF; AcOH / tetrahydrofuran / 2 h / 25 °C

With osmium(VIII) oxide; n-butyllithium; chloro-trimethyl-silane; N-methyl-2-indolinone; tetrabutyl ammonium fluoride; water; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; acetic acid; diethylamine; B-chlorodiisopinocampheylborane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; 1.1: Etherification / 2.1: Hydrolysis / 3.1: Hydrogenation / 4.1: Oxidation / 5.1: Alkylation / 6.1: Etherification / 7.1: hydroxylation / 7.2: cleavage / 8.1: Condensation / 9.1: Hydrolysis;
DOI:10.1016/S0040-4039(99)00755-8