ethyl 2,3-dideoxy-4,5:6,7-di-O-isopropylidene-3C-phenyl-D-manno-heptonate

Base Information

• Chemical Name: ethyl 2,3-dideoxy-4,5:6,7-di-O-isopropylidene-3C-phenyl-D-manno-heptonate
• CAS No.: 89358-84-9
• Molecular Formula: C₂₁H₃₀O₆
• Molecular Weight: 378.466

Synonyms:ethyl 2,3-dideoxy-4,5:6,7-di-O-isopropylidene-3C-phenyl-D-manno-heptonate

Chemical Property of ethyl 2,3-dideoxy-4,5:6,7-di-O-isopropylidene-3C-phenyl-D-manno-heptonate

Chemical Property:

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Technology Process of ethyl 2,3-dideoxy-4,5:6,7-di-O-isopropylidene-3C-phenyl-D-manno-heptonate

There total 2 articles about ethyl 2,3-dideoxy-4,5:6,7-di-O-isopropylidene-3C-phenyl-D-manno-heptonate 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:

2,2:4,5-di-O-isopropylidene-D-arabinose (13039-93-5) → ethyl 2,3-dideoxy-4,5:6,7-di-O-isopropylidene-3C-phenyl-D-manno-heptonate (89358-84-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) sodium hydride / 1.) benzene, 20 deg C, 1 h, 2.) 20 - 25 deg C, 5 min

2: 1.) cuprous iodide / 1.) ether, -10 deg C, 5 min, 2.) -10 - -15 deg C

With copper(l) iodide; sodium hydride;

DOI:10.1039/P19830002629

Reference yield:

(E)-ethyl 3-((4R,5S)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)2,2-dimethyl-1,3-dioxolan-4-yl)acrylate (65391-47-1) + phenylmagnesium bromide → ethyl 2,3-dideoxy-4,5:6,7-di-O-isopropylidene-3C-phenyl-D-manno-heptonate (89358-84-9)

Guidance literature:

With copper(l) iodide; Yield given. Multistep reaction; 1.) ether, -10 deg C, 5 min, 2.) -10 - -15 deg C;

DOI:10.1039/P19830002629

Reference yield: 77.0%

ethyl 2,3-dideoxy-4,5:6,7-di-O-isopropylidene-3C-phenyl-D-manno-heptonate (89358-84-9) → 2,3-dideoxy-3C-phenyl-D-manno-heptono-1,4-lactone (89358-92-9)

Guidance literature:

With hydrogenchloride; In ethanol; at 40 ℃; for 5h;

DOI:10.1039/P19830002629

upstream raw materials:

(E)-ethyl 3-((4R,5S)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)2,2-dimethyl-1,3-dioxolan-4-yl)acrylate

2,2:4,5-di-O-isopropylidene-D-arabinose

Downstream raw materials:

2,3-dideoxy-3C-phenyl-D-manno-heptono-1,4-lactone

ethyl 3C-cyclohexyl-2,3-dideoxy-4,5:6,7-di-O-isopropylidene-D-manno-heptonate

2-deoxy-3,4:5,6-di-O-isopropylidene-2-C-phenyl-aldehydo-D-mannose

3,5-dideoxy-5-C-phenyl-α-D-glycero-D-galacto-2-nonulosonic acid

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