(-)-(2S,3S)-4-(2,5-dimethoxyphenyl)-2,3-dihydroxy-2,3-O-isopropylidene-3-methylbutanal

Base Information

Chemical Name:(-)-(2S,3S)-4-(2,5-dimethoxyphenyl)-2,3-dihydroxy-2,3-O-isopropylidene-3-methylbutanal
CAS No.:130353-17-2
Molecular Formula:C₁₆H₂₂O₅
Molecular Weight:294.348
Hs Code.:

Synonyms:(-)-(2S,3S)-4-(2,5-dimethoxyphenyl)-2,3-dihydroxy-2,3-O-isopropylidene-3-methylbutanal

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Chemical Property of (-)-(2S,3S)-4-(2,5-dimethoxyphenyl)-2,3-dihydroxy-2,3-O-isopropylidene-3-methylbutanal

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Technology Process of (-)-(2S,3S)-4-(2,5-dimethoxyphenyl)-2,3-dihydroxy-2,3-O-isopropylidene-3-methylbutanal

There total 10 articles about (-)-(2S,3S)-4-(2,5-dimethoxyphenyl)-2,3-dihydroxy-2,3-O-isopropylidene-3-methylbutanal 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: 80.0%

: 130353-07-0
(-)-(2S,3R)-5-(2,5-dimethoxyphenyl)-3,4-dihydroxy-3,4-O-isopropylidene-4-methylpentene

: 130353-17-2
(-)-(2S,3S)-4-(2,5-dimethoxyphenyl)-2,3-dihydroxy-2,3-O-isopropylidene-3-methylbutanal

Guidance literature:: With sodium periodate; osmium(VIII) oxide; In diethyl ether; water; for 48h; Ambient temperature;
DOI:10.1021/jo00001a073

Reference yield:

: 109715-12-0
2,3-O-Isopropyliden-2-C-methyl-5-O-p-toluolsulfonyl-D-ribo-pentonsaeure-γ-lacton

: 130353-17-2
(-)-(2S,3S)-4-(2,5-dimethoxyphenyl)-2,3-dihydroxy-2,3-O-isopropylidene-3-methylbutanal

Guidance literature:: Multi-step reaction with 8 steps

1: 95 percent / NaI / butan-2-one / 3 h / Heating

2: 95 percent / Zn, HOAc / H₂O; tetrahydrofuran / 3 h / Ambient temperature

3: diethyl ether

4: 98 percent / LiAlH₄ / tetrahydrofuran / Ambient temperature

5: 1) n-BuLi / 1) ether, hexane, 24h, RT, 2) ether, -78 deg C, 1h

7: Bu₃SnH / AIBN / toluene / 2.5 h / Heating

8: 80 percent / OsO₄, NaIO₄ / diethyl ether; H₂O; various solvent(s) / 48 h / Ambient temperature

With sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; tri-n-butyl-tin hydride; acetic acid; sodium iodide; zinc; 2,2'-azobis(isobutyronitrile); In tetrahydrofuran; diethyl ether; water; toluene; butanone;
DOI:10.1021/jo00001a073

Reference yield:

: 130353-10-5
(+)-(2R,3R)-2,3-dihydroxy-2,3-O-isopropylidene-2-methylpent-4-enoic acid

: 130353-17-2
(-)-(2S,3S)-4-(2,5-dimethoxyphenyl)-2,3-dihydroxy-2,3-O-isopropylidene-3-methylbutanal

Guidance literature:: Multi-step reaction with 6 steps

1: diethyl ether

2: 98 percent / LiAlH₄ / tetrahydrofuran / Ambient temperature

3: 1) n-BuLi / 1) ether, hexane, 24h, RT, 2) ether, -78 deg C, 1h

5: Bu₃SnH / AIBN / toluene / 2.5 h / Heating

6: 80 percent / OsO₄, NaIO₄ / diethyl ether; H₂O; various solvent(s) / 48 h / Ambient temperature

With sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile); In tetrahydrofuran; diethyl ether; water; toluene;
DOI:10.1021/jo00001a073