(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-[4-(2,5-dioxo-pyrrolidin-1-yloxycarbonyloxymethyl)-2-nitro-phenoxy]-tetrahydro-pyran-2-carboxylic acid methyl ester

Base Information

Chemical Name:(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-[4-(2,5-dioxo-pyrrolidin-1-yloxycarbonyloxymethyl)-2-nitro-phenoxy]-tetrahydro-pyran-2-carboxylic acid methyl ester
CAS No.:148579-95-7
Molecular Formula:C₂₅H₂₆N₂O₁₇
Molecular Weight:626.485
Hs Code.:

(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-[4-(2,5-dioxo-pyrrolidin-1-yloxycarbonyloxymethyl)-2-nitro-phenoxy]-tetrahydro-pyran-2-carboxylic acid methyl ester

Synonyms:(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-[4-(2,5-dioxo-pyrrolidin-1-yloxycarbonyloxymethyl)-2-nitro-phenoxy]-tetrahydro-pyran-2-carboxylic acid methyl ester

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-[4-(2,5-dioxo-pyrrolidin-1-yloxycarbonyloxymethyl)-2-nitro-phenoxy]-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-[4-(2,5-dioxo-pyrrolidin-1-yloxycarbonyloxymethyl)-2-nitro-phenoxy]-tetrahydro-pyran-2-carboxylic acid methyl ester

There total 4 articles about (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-[4-(2,5-dioxo-pyrrolidin-1-yloxycarbonyloxymethyl)-2-nitro-phenoxy]-tetrahydro-pyran-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:

: 74124-79-1
di(succinimido) carbonate

: 148579-94-6
(25,3R,45,55,65)-2-(4-(hydroxymethyl)-2-nitrophenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

: 148579-95-7
(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-[4-(2,5-dioxo-pyrrolidin-1-yloxycarbonyloxymethyl)-2-nitro-phenoxy]-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:: With triethylamine; In acetonitrile; at 20 ℃; for 2h;
DOI:10.1021/jm010352w

Reference yield:

: 148579-93-5
(2S,3R,4S,5S,6S)-2-(4-formyl-2-nitrophenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

: 148579-95-7
(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-[4-(2,5-dioxo-pyrrolidin-1-yloxycarbonyloxymethyl)-2-nitro-phenoxy]-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: sodium tetrahydroborate; methanol / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

2: triethylamine / acetonitrile; N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere

With methanol; sodium tetrahydroborate; triethylamine; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/j.bioorg.2018.03.020

Reference yield:

: 7355-18-2
(2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

: 148579-95-7
(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-[4-(2,5-dioxo-pyrrolidin-1-yloxycarbonyloxymethyl)-2-nitro-phenoxy]-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: titanium(IV) bromide / dichloromethane / 24 h / 20 °C / Inert atmosphere

1.2: 4 h / 20 °C / Inert atmosphere

2.1: sodium tetrahydroborate; methanol / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

3.1: triethylamine / acetonitrile; N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere

With methanol; sodium tetrahydroborate; titanium(IV) bromide; triethylamine; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/j.bioorg.2018.03.020