(2'S,3'S)-2-(2'',5''-dimethoxyphenyl)-5'-oxotetrahydrofuran-3'-yl (2S)-2-(acetyloxy)(phenyl)acetate

Base Information

Chemical Name:(2'S,3'S)-2-(2'',5''-dimethoxyphenyl)-5'-oxotetrahydrofuran-3'-yl (2S)-2-(acetyloxy)(phenyl)acetate
CAS No.:1433498-29-3
Molecular Formula:C₂₂H₂₂O₈
Molecular Weight:414.412
Hs Code.:

Synonyms:(2'S,3'S)-2-(2'',5''-dimethoxyphenyl)-5'-oxotetrahydrofuran-3'-yl (2S)-2-(acetyloxy)(phenyl)acetate

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Chemical Property of (2'S,3'S)-2-(2'',5''-dimethoxyphenyl)-5'-oxotetrahydrofuran-3'-yl (2S)-2-(acetyloxy)(phenyl)acetate

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Technology Process of (2'S,3'S)-2-(2'',5''-dimethoxyphenyl)-5'-oxotetrahydrofuran-3'-yl (2S)-2-(acetyloxy)(phenyl)acetate

There total 5 articles about (2'S,3'S)-2-(2'',5''-dimethoxyphenyl)-5'-oxotetrahydrofuran-3'-yl (2S)-2-(acetyloxy)(phenyl)acetate 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: 97.0%

: 1433498-28-2
(4S,5S)-4-hydroxy-5-(2',5'-dimethoxyphenyl)-4,5-dihydrofuran-2(3H)-one

: 7322-88-5
(S)-acetylmandelic acid

: 1433498-29-3
(2'S,3'S)-2-(2'',5''-dimethoxyphenyl)-5'-oxotetrahydrofuran-3'-yl (2S)-2-(acetyloxy)(phenyl)acetate

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane; toluene; at 0 - 20 ℃; Inert atmosphere;
DOI:10.1002/ejoc.201201279

Reference yield:

: 155628-88-9
1-(2',5'-dimethoxyphenyl)prop-2-en-1-ol

: 1433498-29-3
(2'S,3'S)-2-(2'',5''-dimethoxyphenyl)-5'-oxotetrahydrofuran-3'-yl (2S)-2-(acetyloxy)(phenyl)acetate

Guidance literature:: Multi-step reaction with 4 steps

1: pyridine / 0 - 20 °C / Inert atmosphere

2: triphenylphosphine; N-ethyl-N,N-diisopropylamine; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium bromide / methanol / 2 h / 50 °C / 22502.3 Torr / Autoclave

3: (DHQD)₂Phal; sodium hydrogencarbonate; methanesulfonamide / tert-butyl alcohol; water / 24 h / 0 - 20 °C

4: dmap; dicyclohexyl-carbodiimide / toluene; dichloromethane / 0 - 20 °C / Inert atmosphere

With pyridine; dmap; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; methanesulfonamide; (DHQD)₂Phal; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; triphenylphosphine; sodium bromide; In methanol; dichloromethane; water; toluene; tert-butyl alcohol; 3: |Sharpless Dihydroxylation;
DOI:10.1002/ejoc.201201279

Reference yield:

: 1348155-56-5
1-(2',5'-dimethoxyphenyl)allyl acetate

: 1433498-29-3
(2'S,3'S)-2-(2'',5''-dimethoxyphenyl)-5'-oxotetrahydrofuran-3'-yl (2S)-2-(acetyloxy)(phenyl)acetate

Guidance literature:: Multi-step reaction with 3 steps

1: triphenylphosphine; N-ethyl-N,N-diisopropylamine; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium bromide / methanol / 2 h / 50 °C / 22502.3 Torr / Autoclave

2: (DHQD)₂Phal; sodium hydrogencarbonate; methanesulfonamide / tert-butyl alcohol; water / 24 h / 0 - 20 °C

3: dmap; dicyclohexyl-carbodiimide / toluene; dichloromethane / 0 - 20 °C / Inert atmosphere

With dmap; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; methanesulfonamide; (DHQD)₂Phal; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; triphenylphosphine; sodium bromide; In methanol; dichloromethane; water; toluene; tert-butyl alcohol; 2: |Sharpless Dihydroxylation;
DOI:10.1002/ejoc.201201279