ethyl 3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-5-(morpholin-4-yl)-β-L-ido-heptofuranuronate

Base Information

• Chemical Name: ethyl 3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-5-(morpholin-4-yl)-β-L-ido-heptofuranuronate
• CAS No.: 671789-38-1
• Molecular Formula: C₂₃H₃₃NO₇
• Molecular Weight: 435.518

Synonyms:ethyl 3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-5-(morpholin-4-yl)-β-L-ido-heptofuranuronate

Chemical Property of ethyl 3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-5-(morpholin-4-yl)-β-L-ido-heptofuranuronate

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Technology Process of ethyl 3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-5-(morpholin-4-yl)-β-L-ido-heptofuranuronate

There total 2 articles about ethyl 3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-5-(morpholin-4-yl)-β-L-ido-heptofuranuronate 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:

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose (23558-05-6) → ethyl 3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-5-(morpholin-4-yl)-β-L-ido-heptofuranuronate (671789-38-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / toluene / Heating

2: ethanol

In ethanol; toluene; 1: Wittig olefination / 2: Michael addition;

DOI:10.1081/CAR-120016857

Reference yield:

morpholine (110-91-8,99108-56-2) + (1R,2R,3S,4R)-ethyl [3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]heptfuran-5-enuronate (404353-42-0) → ethyl 3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-5-(morpholin-4-yl)-β-L-ido-heptofuranuronate (671789-38-1) + ethyl 3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-5-(morpholin-4-yl)-α-D-gluco-heptofuranuronate

Guidance literature:

In ethanol; Title compound not separated from byproducts;

DOI:10.1081/CAR-120016857

Reference yield: 88.0%

ethyl 3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-5-(morpholin-4-yl)-β-L-ido-heptofuranuronate (671789-38-1) → 3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-5-morpholino-β-L-ido-heptofuranuronic acid

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; at 25 ℃; for 18h;

DOI:10.1016/j.bmc.2003.09.038

upstream raw materials:

morpholine

(1R,2R,3S,4R)-ethyl [3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]heptfuran-5-enuronate

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose

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