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

Base Information

• Chemical Name: N-benzyl-4-[1,2:3,4-di-O-isopropylidene-α-D-galactohexo-1,5-pyranose]methylene-imine
• CAS No.: 51549-65-6
• Molecular Formula: C₁₉H₂₅NO₅
• Molecular Weight: 347.411

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

Chemical Property of N-benzyl-4-[1,2:3,4-di-O-isopropylidene-α-D-galactohexo-1,5-pyranose]methylene-imine

Chemical Property:

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Technology Process of N-benzyl-4-[1,2:3,4-di-O-isopropylidene-α-D-galactohexo-1,5-pyranose]methylene-imine

There total 3 articles about N-benzyl-4-[1,2:3,4-di-O-isopropylidene-α-D-galactohexo-1,5-pyranose]methylene-imine 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: 100.0%

(3aR,5S,5aR,8aS,8bR)-2,2,7,7-Tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-carbaldehyde (4933-77-1) + benzylamine (100-46-9) → N-benzyl-4-[1,2:3,4-di-O-isopropylidene-α-D-galactohexo-1,5-pyranose]methylene-imine (51549-65-6)

Guidance literature:

DOI:10.1016/S0040-4020(00)00410-5

Reference yield:

1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (4064-06-6) → N-benzyl-4-[1,2:3,4-di-O-isopropylidene-α-D-galactohexo-1,5-pyranose]methylene-imine (51549-65-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / PCC / CH₂Cl₂ / 20 °C

2: 100 percent

With pyridinium chlorochromate; In dichloromethane; 1: Oxidation / 2: Condensation;

DOI:10.1016/S0040-4020(00)00410-5

Reference yield:

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

Guidance literature:

aus 1,2;3,4-Di-O-isopropyliden-α-D-galakto-hexodialdo-1,5-pyranose, Benzylamin;

DOI:10.1271/bbb1961.37.2617

upstream raw materials:

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

benzylamine

1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

Downstream raw materials:

cis-1-benzyl-4-[(3aαH,8bαH)-tetrahydro-2,2,7,7-tetrahydro-2,2,7,7-tetramethyl-5H-bis[1,3]dioxolo[4,5-b:4',5'-d]pyran-5-yl]-3-methoxy-azetidin-2-one

(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

(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

(2R,3R,4S,5S,6R)-6-((4'R)-3-benzyloxazolidine-2,3-dione-4-yl)-2,3,4,5-tetrahydroxy-2,3:4,5-bis(di-O-isopropylidene)tetrahydropyran

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