Acetic acid (2S,3R,4S,5R)-4,5-diacetoxy-2-((3aR,5aR,6S)-8-formyl-1-isopropyl-3a,5a-dimethyl-2,3,3a,4,5,5a,6,7-octahydro-cyclohepta[e]inden-6-yloxy)-tetrahydro-pyran-3-yl ester

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Chemical Name:Acetic acid (2S,3R,4S,5R)-4,5-diacetoxy-2-((3aR,5aR,6S)-8-formyl-1-isopropyl-3a,5a-dimethyl-2,3,3a,4,5,5a,6,7-octahydro-cyclohepta[e]inden-6-yloxy)-tetrahydro-pyran-3-yl ester
CAS No.:180609-35-2
Molecular Formula:C₃₁H₄₂O₉
Molecular Weight:558.669
Hs Code.:

Acetic acid (2S,3R,4S,5R)-4,5-diacetoxy-2-((3aR,5aR,6S)-8-formyl-1-isopropyl-3a,5a-dimethyl-2,3,3a,4,5,5a,6,7-octahydro-cyclohepta[e]inden-6-yloxy)-tetrahydro-pyran-3-yl ester

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Chemical Property of Acetic acid (2S,3R,4S,5R)-4,5-diacetoxy-2-((3aR,5aR,6S)-8-formyl-1-isopropyl-3a,5a-dimethyl-2,3,3a,4,5,5a,6,7-octahydro-cyclohepta[e]inden-6-yloxy)-tetrahydro-pyran-3-yl ester

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Technology Process of Acetic acid (2S,3R,4S,5R)-4,5-diacetoxy-2-((3aR,5aR,6S)-8-formyl-1-isopropyl-3a,5a-dimethyl-2,3,3a,4,5,5a,6,7-octahydro-cyclohepta[e]inden-6-yloxy)-tetrahydro-pyran-3-yl ester

There total 20 articles about Acetic acid (2S,3R,4S,5R)-4,5-diacetoxy-2-((3aR,5aR,6S)-8-formyl-1-isopropyl-3a,5a-dimethyl-2,3,3a,4,5,5a,6,7-octahydro-cyclohepta[e]inden-6-yloxy)-tetrahydro-pyran-3-yl ester 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:

: 3068-31-3
2,3,4-tri-O-acetyl-α-D-xylopyranosyl bromide

: (3aR,5aR,6S)-6-Hydroxy-1-isopropyl-3a,5a-dimethyl-2,3,3a,4,5,5a,6,7-octahydro-cyclohepta[e]indene-8-carbaldehyde

: 180854-03-9
Acetic acid (2S,3R,4S,5R)-4,5-diacetoxy-2-((3aS,5aS,6R)-8-formyl-1-isopropyl-3a,5a-dimethyl-2,3,3a,4,5,5a,6,7-octahydro-cyclohepta[e]inden-6-yloxy)-tetrahydro-pyran-3-yl ester

: 180609-35-2
Acetic acid (2S,3R,4S,5R)-4,5-diacetoxy-2-((3aR,5aR,6S)-8-formyl-1-isopropyl-3a,5a-dimethyl-2,3,3a,4,5,5a,6,7-octahydro-cyclohepta[e]inden-6-yloxy)-tetrahydro-pyran-3-yl ester

Guidance literature:: With mercury(II) cyanide; mercury dichloride; In acetonitrile; at 25 ℃; for 0.0583333h; Yield given. Yields of byproduct given;
DOI:10.1021/ja9615379

Reference yield:

: (3aR,5aR,6R,10aS)-6-Hydroxy-1-isopropyl-3a,5a-dimethyl-3,3a,4,5,5a,6,7,10a-octahydro-2H-cyclohepta[e]inden-8-one

: 180609-35-2
Acetic acid (2S,3R,4S,5R)-4,5-diacetoxy-2-((3aR,5aR,6S)-8-formyl-1-isopropyl-3a,5a-dimethyl-2,3,3a,4,5,5a,6,7-octahydro-cyclohepta[e]inden-6-yloxy)-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 7 steps

1: Dess-Martin reagent / CH₂Cl₂ / 0.25 h / Ambient temperature

2: 1.) potassium bis(trimethylsilyl)amide / 1) THF, -78 deg C, 25 min; 2) THF, -78 deg C to rt

3: 75 percent / diisopropylethylamine, Pd(OAc)2, Ph₃P / 2.5 h / Ambient temperature

4: 94 percent / Et₃N / methanol / 12 h / 100 °C

5: 89 percent / LAH / diethyl ether / 0.17 h / -78 °C

6: 94 percent / MnO₂ / CH₂Cl₂ / 12 h / Ambient temperature

7: Hg(CN)2, HgCl₂ / acetonitrile / 0.06 h / Ambient temperature

With manganese(IV) oxide; palladium diacetate; lithium aluminium tetrahydride; mercury(II) cyanide; potassium hexamethylsilazane; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; mercury dichloride; In methanol; diethyl ether; dichloromethane; acetonitrile;
DOI:10.1021/jo9804700

Reference yield:

: (3aR,5aR,6R,10aS)-1-Isopropyl-3a,5a-dimethyl-8-methylene-2,3,3a,4,5,5a,6,7,8,9,10,10a-dodecahydro-cyclohepta[e]inden-6-ol

: 180609-35-2
Acetic acid (2S,3R,4S,5R)-4,5-diacetoxy-2-((3aR,5aR,6S)-8-formyl-1-isopropyl-3a,5a-dimethyl-2,3,3a,4,5,5a,6,7-octahydro-cyclohepta[e]inden-6-yloxy)-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 95 percent / imidazole / dimethylformamide / 24 h / Ambient temperature

2: 77 percent / NaHCO₃, OsO₄, KIO₄ / 2-methyl-propan-2-ol; H₂O / 48 h / Ambient temperature

3: 1.) lithium bis(trimethylsilyl)amide, 2.) PhSeCl, 3.) H₂O₂, aq. NH₄Cl / 1) THF, -78 deg C, 30 min; 2) THF, -78 --> 0 deg C, 1 h; 3) THF, 40 deg C, 30 min

4: HOAc / tetrahydrofuran; H₂O / 2.25 h / 45 °C

5: Dess-Martin reagent / CH₂Cl₂ / 0.25 h / Ambient temperature

6: 1.) potassium bis(trimethylsilyl)amide / 1) THF, -78 deg C, 25 min; 2) THF, -78 deg C to rt

7: 75 percent / diisopropylethylamine, Pd(OAc)2, Ph₃P / 2.5 h / Ambient temperature

8: 94 percent / Et₃N / methanol / 12 h / 100 °C

9: 89 percent / LAH / diethyl ether / 0.17 h / -78 °C

10: 94 percent / MnO₂ / CH₂Cl₂ / 12 h / Ambient temperature

11: Hg(CN)2, HgCl₂ / acetonitrile / 0.06 h / Ambient temperature

With 1H-imidazole; manganese(IV) oxide; palladium diacetate; osmium(VIII) oxide; lithium aluminium tetrahydride; Phenylselenyl chloride; potassium metaperiodate; dihydrogen peroxide; mercury(II) cyanide; potassium hexamethylsilazane; sodium hydrogencarbonate; ammonium chloride; Dess-Martin periodane; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; mercury dichloride; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;
DOI:10.1021/jo9804700