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

Base Information

Chemical Name:(1R,2R,3S,4R)-ethyl [3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]heptfuran-5-enuronate
CAS No.:404353-42-0
Molecular Formula:C₁₉H₂₄O₆
Molecular Weight:348.396
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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

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

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

: 23558-05-6
3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose

: 1099-45-2
ethyl (triphenylphosphoranylidene)acetate

: 404353-42-0
(1R,2R,3S,4R)-ethyl [3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]heptfuran-5-enuronate

Guidance literature:: In toluene; Heating;
DOI:10.1081/CAR-120016857

Reference yield:

: 867-13-0
diethoxyphosphoryl-acetic acid ethyl ester

: 23558-05-6
3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose

: 404353-42-0
(1R,2R,3S,4R)-ethyl [3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]heptfuran-5-enuronate

Guidance literature:: With lithium hydroxide; In tetrahydrofuran; at 25 ℃; for 8h;
DOI:10.1039/c8md00098k

Reference yield:

: 350255-13-9
1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

: 404353-42-0
(1R,2R,3S,4R)-ethyl [3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]heptfuran-5-enuronate

Guidance literature:: Multi-step reaction with 4 steps

1: sodium hydride; tetrabutylammomium bromide / tetrahydrofuran / 12 h / 0 - 25 °C

2: acetic acid / water / 8 h / 25 °C

3: sodium periodate / water; methanol / 3 h / 0 - 25 °C

4: lithium hydroxide / tetrahydrofuran / 8 h / 25 °C

With sodium periodate; tetrabutylammomium bromide; sodium hydride; acetic acid; lithium hydroxide; In tetrahydrofuran; methanol; water; 4: |Horner-Wadsworth-Emmons Olefination;
DOI:10.1039/c8md00098k