(1R,6R,7S,8R,9R,10R)-5-acetyl-7,9-dibenzyloxy-8-methyl-10-hydroxybicyclo[4.4.0]dec-4-en-3-one

Base Information

Chemical Name:(1R,6R,7S,8R,9R,10R)-5-acetyl-7,9-dibenzyloxy-8-methyl-10-hydroxybicyclo[4.4.0]dec-4-en-3-one
CAS No.:188557-64-4
Molecular Formula:C₂₇H₃₀O₅
Molecular Weight:434.532
Hs Code.:

Synonyms:(1R,6R,7S,8R,9R,10R)-5-acetyl-7,9-dibenzyloxy-8-methyl-10-hydroxybicyclo[4.4.0]dec-4-en-3-one

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Chemical Property of (1R,6R,7S,8R,9R,10R)-5-acetyl-7,9-dibenzyloxy-8-methyl-10-hydroxybicyclo[4.4.0]dec-4-en-3-one

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Technology Process of (1R,6R,7S,8R,9R,10R)-5-acetyl-7,9-dibenzyloxy-8-methyl-10-hydroxybicyclo[4.4.0]dec-4-en-3-one

There total 17 articles about (1R,6R,7S,8R,9R,10R)-5-acetyl-7,9-dibenzyloxy-8-methyl-10-hydroxybicyclo[4.4.0]dec-4-en-3-one 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%

: 188557-59-7
(4R,4aR,5S,6R,7R,8R,8aR)-4-Acetyl-5,7-bis-benzyloxy-8-hydroxy-6-methyl-octahydro-naphthalen-2-one

: 188557-64-4
(1R,6R,7S,8R,9R,10R)-5-acetyl-7,9-dibenzyloxy-8-methyl-10-hydroxybicyclo[4.4.0]dec-4-en-3-one

Guidance literature:: (4R,4aR,5S,6R,7R,8R,8aR)-4-Acetyl-5,7-bis-benzyloxy-8-hydroxy-6-methyl-octahydro-naphthalen-2-one; With potassium tert-butylate; potassium hydride; In tetrahydrofuran; Petroleum ether; at 20 ℃; for 0.416667h;

With iron(III) chloride; In tetrahydrofuran; N,N-dimethyl-formamide; Petroleum ether; at -78 ℃; for 0.333333h;
DOI:10.1016/S0040-4020(01)00155-7

Reference yield:

: 101199-21-7
(meso)-(1R*,2R*,3S*,6R*,7S*,8S*)-1,8,9,10-Tetrachlor-11,11-dimethoxytricyclo<6.2.1.0^2,7>undeca-4,9-dien-3,6-diol

: 188557-64-4
(1R,6R,7S,8R,9R,10R)-5-acetyl-7,9-dibenzyloxy-8-methyl-10-hydroxybicyclo[4.4.0]dec-4-en-3-one

Guidance literature:: Multi-step reaction with 14 steps

1: 75 percent / H⁺, molecular sieves / CH₂Cl₂ / 24 h / Ambient temperature

2: 100 percent / 2,6-lutidine / dimethylformamide / 2 h / 0 °C

3: 92 percent / CrO₃, H₂SO₄ / acetone / 0.42 h / 0 °C

4: Et₃N / diethyl ether / 0 °C

5: OsO₄, NMO / tetrahydrofuran; H₂O; acetone / 18 h / Ambient temperature

6: NaBH₄ / methanol / 1 h / 0 °C

7: PPTS / 5 h / Ambient temperature

8: 3 h / Heating

9: MeOH, H⁺ / 15 h / Ambient temperature

10: NaH, Bu₄N⁺I^- / tetrahydrofuran / 2 h / Heating

11: aq. HCl / dioxane / 3 h / Heating

12: 65 percent / toluene / 15 h / 0 °C

13: 81 percent / camphorsulfonic acid, 5M LiClO₄ / diethyl ether / 2 h / Heating

14: 1.) KH, KOt-Bu, 2.) FeCl₃ / 1.) THF, room temperature, 30 min, 2.) DMF, 1 h

With 2,6-dimethylpyridine; chromium(VI) oxide; hydrogenchloride; methanol; sodium tetrahydroborate; osmium(VIII) oxide; N-methyl-2-indolinone; molecular sieve; sulfuric acid; camphor-10-sulfonic acid; potassium tert-butylate; lithium perchlorate; pyridinium p-toluenesulfonate; hydrogen cation; iron(III) chloride; tetra-(n-butyl)ammonium iodide; potassium hydride; sodium hydride; triethylamine; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1016/S0040-4020(97)00065-3

Reference yield:

: 100-39-0
benzyl bromide

: 188557-64-4
(1R,6R,7S,8R,9R,10R)-5-acetyl-7,9-dibenzyloxy-8-methyl-10-hydroxybicyclo[4.4.0]dec-4-en-3-one

Guidance literature:: Multi-step reaction with 5 steps

1: NaH, Bu₄N⁺I^- / tetrahydrofuran / 2 h / Heating

2: aq. HCl / dioxane / 3 h / Heating

3: 65 percent / toluene / 15 h / 0 °C

4: 81 percent / camphorsulfonic acid, 5M LiClO₄ / diethyl ether / 2 h / Heating

5: 1.) KH, KOt-Bu, 2.) FeCl₃ / 1.) THF, room temperature, 30 min, 2.) DMF, 1 h

With hydrogenchloride; camphor-10-sulfonic acid; potassium tert-butylate; lithium perchlorate; iron(III) chloride; tetra-(n-butyl)ammonium iodide; potassium hydride; sodium hydride; In tetrahydrofuran; 1,4-dioxane; diethyl ether; toluene;
DOI:10.1016/S0040-4020(97)00065-3