(1R,2R,3S)-3-O-benzoyl-5-(benzyloxymethyl)-1,2-O-ethylpropylidene-4-cyclohexene-1,2,3-triol

Base Information

Chemical Name:(1R,2R,3S)-3-O-benzoyl-5-(benzyloxymethyl)-1,2-O-ethylpropylidene-4-cyclohexene-1,2,3-triol
CAS No.:827043-65-2
Molecular Formula:C₂₆H₂₈O₆
Molecular Weight:436.505
Hs Code.:

Synonyms:(1R,2R,3S)-3-O-benzoyl-5-(benzyloxymethyl)-1,2-O-ethylpropylidene-4-cyclohexene-1,2,3-triol

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Chemical Property of (1R,2R,3S)-3-O-benzoyl-5-(benzyloxymethyl)-1,2-O-ethylpropylidene-4-cyclohexene-1,2,3-triol

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Technology Process of (1R,2R,3S)-3-O-benzoyl-5-(benzyloxymethyl)-1,2-O-ethylpropylidene-4-cyclohexene-1,2,3-triol

There total 1 articles about (1R,2R,3S)-3-O-benzoyl-5-(benzyloxymethyl)-1,2-O-ethylpropylidene-4-cyclohexene-1,2,3-triol 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%

: 98-88-4
benzoyl chloride

: 374687-82-8
(1R,2S,3S)-1,2-O-ethylpropylidene-5-(hydroxymethyl)-4-cyclohexene-1,2,3-triol

: 827043-65-2
(1R,2R,3S)-3-O-benzoyl-5-(benzyloxymethyl)-1,2-O-ethylpropylidene-4-cyclohexene-1,2,3-triol

Guidance literature:: With pyridine; dmap; at 20 ℃; for 2h;
DOI:10.1021/ja0470158

Reference yield: 93.0%

: 827043-65-2
(1R,2R,3S)-3-O-benzoyl-5-(benzyloxymethyl)-1,2-O-ethylpropylidene-4-cyclohexene-1,2,3-triol

: 827043-66-3
(1R,2R,3S,4R,5R)-3-O-benzoyl-5-(benzyloxymethyl)-1,2-O-ethylpropylidene-4-cyclohexene-1,2,3,4,5-pentol

Guidance literature:: With osmium(VIII) oxide; N-methyl-2-indolinone; In acetone; at 20 ℃; for 2h;
DOI:10.1021/ja0470158

Reference yield:

: 827043-65-2
(1R,2R,3S)-3-O-benzoyl-5-(benzyloxymethyl)-1,2-O-ethylpropylidene-4-cyclohexene-1,2,3-triol

: bis[(1S,2R,3S,4R)-2,3,4-trihydroxy-5-(hydroxymethyl)-5-cyclohexenyl]amine

Guidance literature:: Multi-step reaction with 11 steps

1: 93 percent / NMO; aq. OsO₄ / acetone / 2 h / 20 °C

2: 98 percent / DMAP; pyridine / 1 h / 0 °C

3: 92 percent / pyridine; SOCl₂ / CH₂Cl₂ / 24 h / 20 °C

4: 98 percent / aq. TFA / CH₂Cl₂ / 12 h / 20 °C

5: 88 percent / Et₃N / CH₂Cl₂ / 2 h / Heating

6: 85 percent / K₂CO₃; methanol / 1 h / 20 °C

7: 89 percent / p-TsOH / acetone / 12 h / 20 °C

8: DIBAL-H / tetrahydrofuran; hexane / 2 h / 20 °C

9: 21 mg / p-TsOH / acetone / 12 h / 20 °C

10: 94 percent / TMPP; Pd(dba)2; Et₃N / acetonitrile / 12 h / 20 °C

11: 92 percent / aq. TFA / CH₂Cl₂ / 1 h / 20 °C

With pyridine; methanol; dmap; osmium(VIII) oxide; thionyl chloride; N-methyl-2-indolinone; 5,10,15,20-tetrakis(4-methoxyphenyl)porphyrin; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; triethylamine; trifluoroacetic acid; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; hexane; dichloromethane; acetone; acetonitrile;
DOI:10.1021/ja0470158