(1R,2R,3R,4R)-1-O-acetyl-2,3-di-O-benzyl-4-benzyloxymethylcyclohex-5-ene-1,2,3-triol

Base Information

Chemical Name:(1R,2R,3R,4R)-1-O-acetyl-2,3-di-O-benzyl-4-benzyloxymethylcyclohex-5-ene-1,2,3-triol
CAS No.:151693-64-0
Molecular Formula:C₃₀H₃₂O₅
Molecular Weight:472.581
Hs Code.:

Synonyms:(1R,2R,3R,4R)-1-O-acetyl-2,3-di-O-benzyl-4-benzyloxymethylcyclohex-5-ene-1,2,3-triol

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Chemical Property of (1R,2R,3R,4R)-1-O-acetyl-2,3-di-O-benzyl-4-benzyloxymethylcyclohex-5-ene-1,2,3-triol

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Technology Process of (1R,2R,3R,4R)-1-O-acetyl-2,3-di-O-benzyl-4-benzyloxymethylcyclohex-5-ene-1,2,3-triol

There total 11 articles about (1R,2R,3R,4R)-1-O-acetyl-2,3-di-O-benzyl-4-benzyloxymethylcyclohex-5-ene-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: 96.0%

: 108-24-7
acetic anhydride

: 161596-04-9
(1R,2R,3R,4R)-2,3-di-O-benzyl-4-benzyloxymethylcyclohex-5-ene-1,2,3-triol

: 151693-64-0
(1R,2R,3R,4R)-1-O-acetyl-2,3-di-O-benzyl-4-benzyloxymethylcyclohex-5-ene-1,2,3-triol

Guidance literature:: With pyridine; dmap; In dichloromethane; for 24h; Ambient temperature;
DOI:10.1039/c39930000995

Reference yield: 83.0%

: 161484-59-9
(1R,2R,3R,4S,6R)-3-O-acetyl-1,2-di-O-benzyl-6-benzyloxymethyl-4-iodocyclohexane-1,2,3-triol

: 151693-64-0
(1R,2R,3R,4R)-1-O-acetyl-2,3-di-O-benzyl-4-benzyloxymethylcyclohex-5-ene-1,2,3-triol

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In xylene; for 12h; Heating;
DOI:10.1039/P19940002017

Reference yield:

: 135735-91-0
(1R,2R,3S,4R,5R)-3-O-Benzyl-5-benzyloxymethyl-1,2-O-cyclohexylidene-cyclohexan-1,2,3,4-tetraol

: 151693-64-0
(1R,2R,3R,4R)-1-O-acetyl-2,3-di-O-benzyl-4-benzyloxymethylcyclohex-5-ene-1,2,3-triol

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) NaH, 2.) tetrabutylammonium iodide / 1.) THF, 0 deg C, 1 h, 2.) 60 deg C, 12 h

2: 90 percent / aq. TFA / CH₂Cl₂ / 24 h / Ambient temperature

3: 93 percent / Et₃N, thionyl chloride / CH₂Cl₂ / 0.08 h / 0 °C

4: 89 percent / aq. RuCl₃, NaIO₄ / CCl₄; acetonitrile / 1 h / 0 °C

5: 1.) Bu₄NI, 2.) conc. H₂SO₄ / 1.) THF, reflux, 6 h, 2.) H₂O, 60 deg C, 30 min

6: 95 percent / DMAP / pyridine; CH₂Cl₂ / 24 h / Ambient temperature

7: 83 percent / DBU / xylene / 12 h / Heating

With dmap; ruthenium trichloride; sodium periodate; thionyl chloride; sulfuric acid; tetra-(n-butyl)ammonium iodide; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trifluoroacetic acid; In pyridine; tetrachloromethane; dichloromethane; acetonitrile; xylene;
DOI:10.1039/P19940002017