(2S,5R,6R)-5,6-dimethoxy-5,6-dimethyl-[1,4]dioxane-2-carboxylic acid methyl ester

Base Information

Chemical Name:(2S,5R,6R)-5,6-dimethoxy-5,6-dimethyl-[1,4]dioxane-2-carboxylic acid methyl ester
CAS No.:503321-03-7
Molecular Formula:C₁₀H₁₈O₆
Molecular Weight:234.249
Hs Code.:

Synonyms:(2S,5R,6R)-5,6-dimethoxy-5,6-dimethyl-[1,4]dioxane-2-carboxylic acid methyl ester

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Chemical Property of (2S,5R,6R)-5,6-dimethoxy-5,6-dimethyl-[1,4]dioxane-2-carboxylic acid methyl ester

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Technology Process of (2S,5R,6R)-5,6-dimethoxy-5,6-dimethyl-[1,4]dioxane-2-carboxylic acid methyl ester

There total 1 articles about (2S,5R,6R)-5,6-dimethoxy-5,6-dimethyl-[1,4]dioxane-2-carboxylic acid methyl 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: 89.0%

: 1421045-66-0
2,2,2-trichloro-N-((S,E)-4-((2R,5R,6R)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxan-2-yl)-2-phenylbut-3-en-2-yl)acetamide

: 74-88-4
methyl iodide

: 1421045-70-6
(R)-methyl 2-phenyl-2-(2,2,2-trichloroacetamido)propanoate

: 503321-03-7
(2S,5R,6R)-5,6-dimethoxy-5,6-dimethyl-[1,4]dioxane-2-carboxylic acid methyl ester

Guidance literature:: 2,2,2-trichloro-N-((S,E)-4-((2R,5R,6R)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxan-2-yl)-2-phenylbut-3-en-2-yl)acetamide; With sodium periodate; ruthenium(III) trichloride hydrate; In tetrachloromethane; water; acetonitrile; at 20 ℃; Inert atmosphere;

methyl iodide; With potassium carbonate; In acetonitrile; at 50 - 55 ℃; for 11h; Inert atmosphere;
DOI:10.1002/asia.201200859

Reference yield: 71.0%

: methyl lithium lithium bromide complex

: 503321-03-7
(2S,5R,6R)-5,6-dimethoxy-5,6-dimethyl-[1,4]dioxane-2-carboxylic acid methyl ester

: 503321-10-6
1-((2S,5R,6R)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxan-2-yl)ethanone

Guidance literature:: In diethyl ether; dichloromethane; at -78 ℃; for 2h;
DOI:10.1016/j.tet.2008.01.010

Reference yield:

: 503321-03-7
(2S,5R,6R)-5,6-dimethoxy-5,6-dimethyl-[1,4]dioxane-2-carboxylic acid methyl ester

: (3S,6R,2'S,5'R,6'R)-6-(5',6'-dimethoxy-5',6'-dimethyl-1',4'-dioxan-2'-yl)-3-hydroxy-3-(2''-oxo-2''-phenylethyl)dihydro-2H-pyran-2,4(3H)-dione

Guidance literature:: Multi-step reaction with 7 steps

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.25 h / -78 °C

2.2: -78 - 20 °C

3.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / -78 °C

4.1: sodium hydroxide / water; diethyl ether / 0.17 h / 20 °C

5.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 4 h / 20 °C

6.1: Sudan III; ozone / dichloromethane / -78 °C

7.1: N-(benzenesulfonyl)-3-phenyloxaziridine; sodium hydride / tetrahydrofuran; mineral oil / 1 h / -78 °C / Inert atmosphere

With lithium aluminium tetrahydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; oxalyl dichloride; boron trifluoride diethyl etherate; sodium hydride; ozone; dimethyl sulfoxide; N-(benzenesulfonyl)-3-phenyloxaziridine; sodium hydroxide; Sudan III; In tetrahydrofuran; diethyl ether; dichloromethane; water; mineral oil; 3.1: |Mukaiyama Aldol Addition / 5.1: |Tsuji-Trost Allylation;
DOI:10.1055/s-0035-1562539