(2R,3R,4S,5S,6R)-6-((3'S,4'R)-1-benzyl-3-hydroxyazetidin-2-one-4-yl)-2,3,4,5-tetrahydroxy-2,3:4,5-bis(di-O-isopropylidene)tetrahydropyran

Base Information

Chemical Name:(2R,3R,4S,5S,6R)-6-((3'S,4'R)-1-benzyl-3-hydroxyazetidin-2-one-4-yl)-2,3,4,5-tetrahydroxy-2,3:4,5-bis(di-O-isopropylidene)tetrahydropyran
CAS No.:213480-54-7
Molecular Formula:C₂₁H₂₇NO₇
Molecular Weight:405.448
Hs Code.:

Synonyms:(2R,3R,4S,5S,6R)-6-((3'S,4'R)-1-benzyl-3-hydroxyazetidin-2-one-4-yl)-2,3,4,5-tetrahydroxy-2,3:4,5-bis(di-O-isopropylidene)tetrahydropyran

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Chemical Property of (2R,3R,4S,5S,6R)-6-((3'S,4'R)-1-benzyl-3-hydroxyazetidin-2-one-4-yl)-2,3,4,5-tetrahydroxy-2,3:4,5-bis(di-O-isopropylidene)tetrahydropyran

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Technology Process of (2R,3R,4S,5S,6R)-6-((3'S,4'R)-1-benzyl-3-hydroxyazetidin-2-one-4-yl)-2,3,4,5-tetrahydroxy-2,3:4,5-bis(di-O-isopropylidene)tetrahydropyran

There total 4 articles about (2R,3R,4S,5S,6R)-6-((3'S,4'R)-1-benzyl-3-hydroxyazetidin-2-one-4-yl)-2,3,4,5-tetrahydroxy-2,3:4,5-bis(di-O-isopropylidene)tetrahydropyran 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: 95.0%

: 213480-52-5
(2R,3R,4S,5S,6R)-6-((3'S,4'R)-3-acetoxy-1-benzylazetidin-2-one-4-yl)-2,3,4,5-tetrahydroxy-2,3:4,5-bis(di-O-isopropylidene)tetrahydropyran

: 213480-54-7
(2R,3R,4S,5S,6R)-6-((3'S,4'R)-1-benzyl-3-hydroxyazetidin-2-one-4-yl)-2,3,4,5-tetrahydroxy-2,3:4,5-bis(di-O-isopropylidene)tetrahydropyran

Guidance literature:: With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; water; at 0 ℃; for 3h;
DOI:10.1021/jo980354x

Reference yield:

: 51549-65-6
N-benzyl-4-[1,2:3,4-di-O-isopropylidene-α-D-galactohexo-1,5-pyranose]methylene-imine

: 213480-54-7
(2R,3R,4S,5S,6R)-6-((3'S,4'R)-1-benzyl-3-hydroxyazetidin-2-one-4-yl)-2,3,4,5-tetrahydroxy-2,3:4,5-bis(di-O-isopropylidene)tetrahydropyran

Guidance literature:: Multi-step reaction with 2 steps

1: 58 percent / triethylamine / toluene; CH₂Cl₂ / -78 - 20 °C

2: 95 percent / LiOH; H₂O₂ / tetrahydrofuran; H₂O / 3 h / 0 °C

With lithium hydroxide; dihydrogen peroxide; triethylamine; In tetrahydrofuran; dichloromethane; water; toluene; 1: Cycloaddition / 2: Hydrolysis;
DOI:10.1021/jo980354x

Reference yield:

: 4933-77-1
(3aR,5S,5aR,8aS,8bR)-2,2,7,7-Tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-carbaldehyde

: 213480-54-7
(2R,3R,4S,5S,6R)-6-((3'S,4'R)-1-benzyl-3-hydroxyazetidin-2-one-4-yl)-2,3,4,5-tetrahydroxy-2,3:4,5-bis(di-O-isopropylidene)tetrahydropyran

Guidance literature:: Multi-step reaction with 3 steps

1: 4A MS / CH₂Cl₂ / 1 h / 0 °C

2: 58 percent / triethylamine / toluene; CH₂Cl₂ / -78 - 20 °C

3: 95 percent / LiOH; H₂O₂ / tetrahydrofuran; H₂O / 3 h / 0 °C

With lithium hydroxide; dihydrogen peroxide; triethylamine; In tetrahydrofuran; dichloromethane; water; toluene; 1: Condensation / 2: Cycloaddition / 3: Hydrolysis;
DOI:10.1021/jo980354x