isopropyl 6-O-acetyl-3-[hydroxy-(4-nitrophenyl)methyl]-2,3-dideoxy-α-D-glycero-hex-2-enopyranos-4-uloside

Base Information

Chemical Name:isopropyl 6-O-acetyl-3-[hydroxy-(4-nitrophenyl)methyl]-2,3-dideoxy-α-D-glycero-hex-2-enopyranos-4-uloside
CAS No.:819803-40-2
Molecular Formula:C₁₈H₂₁NO₈
Molecular Weight:379.367
Hs Code.:

Synonyms:isopropyl 6-O-acetyl-3-[hydroxy-(4-nitrophenyl)methyl]-2,3-dideoxy-α-D-glycero-hex-2-enopyranos-4-uloside

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Chemical Property of isopropyl 6-O-acetyl-3-[hydroxy-(4-nitrophenyl)methyl]-2,3-dideoxy-α-D-glycero-hex-2-enopyranos-4-uloside

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Technology Process of isopropyl 6-O-acetyl-3-[hydroxy-(4-nitrophenyl)methyl]-2,3-dideoxy-α-D-glycero-hex-2-enopyranos-4-uloside

There total 5 articles about isopropyl 6-O-acetyl-3-[hydroxy-(4-nitrophenyl)methyl]-2,3-dideoxy-α-D-glycero-hex-2-enopyranos-4-uloside 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: 64.0%

: 555-16-8
4-nitrobenzaldehdye

: 819803-37-7
isopropyl 6-O-acetyl-2,3-dideoxy-α-D-glycero-hex-2-enopyranosid-4-ulose

: 819803-40-2
isopropyl 6-O-acetyl-3-[hydroxy-(4-nitrophenyl)methyl]-2,3-dideoxy-α-D-glycero-hex-2-enopyranos-4-uloside

Guidance literature:: With titanium tetrachloride; tetra-(n-butyl)ammonium iodide; In dichloromethane; at -78 - -30 ℃; for 5h;
DOI:10.1016/j.tet.2004.09.086

Reference yield:

: 2873-29-2
D-glucal triacetate

: 819803-40-2
isopropyl 6-O-acetyl-3-[hydroxy-(4-nitrophenyl)methyl]-2,3-dideoxy-α-D-glycero-hex-2-enopyranos-4-uloside

Guidance literature:: Multi-step reaction with 5 steps

1: I₂ / tetrahydrofuran / 3 h / 20 °C

2: NaOMe / methanol / 2 h / 20 °C

3: MnO₂ / CHCl₃ / 48 h / 20 °C

4: pyridine / 0 - 5 °C

5: TiCl₄; tetrabutylammonium iodide / CH₂Cl₂ / -78 - -30 °C

With pyridine; manganese(IV) oxide; sodium methylate; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; iodine; In tetrahydrofuran; methanol; dichloromethane; chloroform; 1: Ferrier rearrangement / 5: Morita-Baylis-Hillman reaction;
DOI:10.1021/jm070110h

Reference yield:

: 23339-26-6,56196-34-0
isopropyl 2,3-dideoxy-α-D-erythro-hex-2-enopyranoside

: 819803-40-2
isopropyl 6-O-acetyl-3-[hydroxy-(4-nitrophenyl)methyl]-2,3-dideoxy-α-D-glycero-hex-2-enopyranos-4-uloside

Guidance literature:: Multi-step reaction with 3 steps

1: MnO₂ / CHCl₃ / 48 h / 20 °C

2: pyridine / 0 - 5 °C

3: TiCl₄; tetrabutylammonium iodide / CH₂Cl₂ / -78 - -30 °C

With pyridine; manganese(IV) oxide; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; In dichloromethane; chloroform; 3: Morita-Baylis-Hillman reaction;
DOI:10.1021/jm070110h