(-)-(2Z)-Ethyl 3-<(2'R,3'R,4'R,5'R)-3'-benzyloxy-4',5'-isopropylidenedioxytetrahydrofuran-2'-yl>prop-2-enoate

Base Information

Chemical Name:(-)-(2Z)-Ethyl 3-<(2'R,3'R,4'R,5'R)-3'-benzyloxy-4',5'-isopropylidenedioxytetrahydrofuran-2'-yl>prop-2-enoate
CAS No.:145741-64-6
Molecular Formula:C₁₉H₂₄O₆
Molecular Weight:348.396
Hs Code.:

Synonyms:(-)-(2Z)-Ethyl 3-<(2'R,3'R,4'R,5'R)-3'-benzyloxy-4',5'-isopropylidenedioxytetrahydrofuran-2'-yl>prop-2-enoate

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Chemical Property of (-)-(2Z)-Ethyl 3-<(2'R,3'R,4'R,5'R)-3'-benzyloxy-4',5'-isopropylidenedioxytetrahydrofuran-2'-yl>prop-2-enoate

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Technology Process of (-)-(2Z)-Ethyl 3-<(2'R,3'R,4'R,5'R)-3'-benzyloxy-4',5'-isopropylidenedioxytetrahydrofuran-2'-yl>prop-2-enoate

There total 6 articles about (-)-(2Z)-Ethyl 3-<(2'R,3'R,4'R,5'R)-3'-benzyloxy-4',5'-isopropylidenedioxytetrahydrofuran-2'-yl>prop-2-enoate 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: 90.0%

: 34370-89-3
(3aR,5R,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbaldehyde

: 1099-45-2
ethyl (triphenylphosphoranylidene)acetate

: 108788-48-3,108788-49-4,136838-95-4,136839-11-7,145741-63-5,145741-64-6
ethyl 3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-β-L-lyxo-hept-5-enofuranuronate

Guidance literature:: In acetonitrile; for 2h; Heating;
DOI:10.1021/jo00024a022

Reference yield: 76.0%

: 63593-02-2
3-O-benzyl-1,2-O-isopropylidene-α-D-ribo-pentodialdo-1,4-furanose

: 1099-45-2
ethyl (triphenylphosphoranylidene)acetate

: 145741-64-6
(-)-(2Z)-Ethyl 3-<(2'R,3'R,4'R,5'R)-3'-benzyloxy-4',5'-isopropylidenedioxytetrahydrofuran-2'-yl>prop-2-enoate

: 145741-63-5
(+)-(2E)-Ethyl 3-<(2'R,3'R,4'R,5'R)-3'-benzyloxy-4',5'-isopropylidenedioxytetrahydrofuran-2'-yl>prop-2-enoate

Guidance literature:: With benzoic acid; In tetrahydrofuran; for 4.5h; Ambient temperature;
DOI:10.1039/P19920002625

Reference yield:

: 14686-89-6
(1,2:5,6)-di-O-isopropylidene-D-gulose

: 145741-64-6
(-)-(2Z)-Ethyl 3-<(2'R,3'R,4'R,5'R)-3'-benzyloxy-4',5'-isopropylidenedioxytetrahydrofuran-2'-yl>prop-2-enoate

Guidance literature:: Multi-step reaction with 4 steps

1: 1) NaH, 2) tetrabutylammonium iodide / 1) THF, r.t., 45 min, 2) reflux, 1 h

2: conc. HCl / H₂O; methanol / 23 h / Ambient temperature

3: 1.19 g / sodium metaperiodate / methanol / 30 h / Ambient temperature

4: 4 percent / benzoic acid / tetrahydrofuran / 4.5 h / Ambient temperature

With hydrogenchloride; sodium periodate; tetra-(n-butyl)ammonium iodide; sodium hydride; benzoic acid; In tetrahydrofuran; methanol; water;
DOI:10.1039/P19920002625