(1R,2S,3R,4S)-2,3-di-O-benzyl-4-benzyloxymethyl-1-(O-tert-butyldimethylsilyl)cyclohex-5-ene-1,2,3-triol

Base Information

Chemical Name:(1R,2S,3R,4S)-2,3-di-O-benzyl-4-benzyloxymethyl-1-(O-tert-butyldimethylsilyl)cyclohex-5-ene-1,2,3-triol
CAS No.:161596-08-3
Molecular Formula:C₃₄H₄₄O₄Si
Molecular Weight:544.806
Hs Code.:

Synonyms:(1R,2S,3R,4S)-2,3-di-O-benzyl-4-benzyloxymethyl-1-(O-tert-butyldimethylsilyl)cyclohex-5-ene-1,2,3-triol

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Chemical Property of (1R,2S,3R,4S)-2,3-di-O-benzyl-4-benzyloxymethyl-1-(O-tert-butyldimethylsilyl)cyclohex-5-ene-1,2,3-triol

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Technology Process of (1R,2S,3R,4S)-2,3-di-O-benzyl-4-benzyloxymethyl-1-(O-tert-butyldimethylsilyl)cyclohex-5-ene-1,2,3-triol

There total 11 articles about (1R,2S,3R,4S)-2,3-di-O-benzyl-4-benzyloxymethyl-1-(O-tert-butyldimethylsilyl)cyclohex-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%

: 18162-48-6
tert-butyldimethylsilyl chloride

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

: 161596-08-3
(1R,2S,3R,4S)-2,3-di-O-benzyl-4-benzyloxymethyl-1-(O-tert-butyldimethylsilyl)cyclohex-5-ene-1,2,3-triol

Guidance literature:: With 1H-imidazole; dmap; In N,N-dimethyl-formamide; Ambient temperature;
DOI:10.1039/P19940002017

Reference yield:

: 100-39-0
benzyl bromide

: 161596-08-3
(1R,2S,3R,4S)-2,3-di-O-benzyl-4-benzyloxymethyl-1-(O-tert-butyldimethylsilyl)cyclohex-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.) NaBH₄, 2.) conc. H₂SO₄ / 1.) EtOH, 0 deg C, 2 h, 2.) H₂O, room temperature, 2 h

6: 1.) MCPBA, 2.) iPr₂NEt / 1.) -70 deg C, 10 min, -70 deg C to room temperature, 2.) toluene, 80 deg C, 1 h

7: 96 percent / imidazole, DMAP / dimethylformamide / Ambient temperature

With 1H-imidazole; dmap; ruthenium trichloride; sodium tetrahydroborate; sodium periodate; thionyl chloride; sulfuric acid; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In tetrachloromethane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
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

: 161596-08-3
(1R,2S,3R,4S)-2,3-di-O-benzyl-4-benzyloxymethyl-1-(O-tert-butyldimethylsilyl)cyclohex-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.) NaBH₄, 2.) conc. H₂SO₄ / 1.) EtOH, 0 deg C, 2 h, 2.) H₂O, room temperature, 2 h

6: 1.) MCPBA, 2.) iPr₂NEt / 1.) -70 deg C, 10 min, -70 deg C to room temperature, 2.) toluene, 80 deg C, 1 h

7: 96 percent / imidazole, DMAP / dimethylformamide / Ambient temperature

With 1H-imidazole; dmap; ruthenium trichloride; sodium tetrahydroborate; sodium periodate; thionyl chloride; sulfuric acid; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In tetrachloromethane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1039/P19940002017