(1S,2S,5R,6R)-5-Acetyl-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-formyl-2-methyl-cyclohexanecarboxylic acid methyl ester

Base Information

Chemical Name:(1S,2S,5R,6R)-5-Acetyl-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-formyl-2-methyl-cyclohexanecarboxylic acid methyl ester
CAS No.:139694-40-9
Molecular Formula:C₁₇H₂₆O₆
Molecular Weight:326.39
Hs Code.:

Synonyms:(1S,2S,5R,6R)-5-Acetyl-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-formyl-2-methyl-cyclohexanecarboxylic acid methyl ester

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Chemical Property of (1S,2S,5R,6R)-5-Acetyl-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-formyl-2-methyl-cyclohexanecarboxylic acid methyl ester

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Technology Process of (1S,2S,5R,6R)-5-Acetyl-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-formyl-2-methyl-cyclohexanecarboxylic acid methyl ester

There total 1 articles about (1S,2S,5R,6R)-5-Acetyl-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-formyl-2-methyl-cyclohexanecarboxylic acid methyl 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:

: 141271-37-6
(1R,2S,3R,4R)-3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-1,5-dimethyl-bicyclo[2.2.2]oct-5-ene-2-carboxylic acid methyl ester

: 139694-40-9
(1S,2S,5R,6R)-5-Acetyl-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-formyl-2-methyl-cyclohexanecarboxylic acid methyl ester

Guidance literature:: With dimethylsulfide; ozone; Yield given. Multistep reaction;
DOI:10.1248/cpb.40.556

Reference yield: 79.0%

: 75-11-6
diiodomethane

: 139694-40-9
(1S,2S,5R,6R)-5-Acetyl-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-formyl-2-methyl-cyclohexanecarboxylic acid methyl ester

: 141210-95-9
(1S,2R,5R,6R)-5-Acetyl-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-2-vinyl-cyclohexanecarboxylic acid methyl ester

Guidance literature:: With trimethylaluminum; zinc;
DOI:10.1248/cpb.40.556

Reference yield:

: 139694-40-9
(1S,2S,5R,6R)-5-Acetyl-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-formyl-2-methyl-cyclohexanecarboxylic acid methyl ester

: (1R,2S,3R,6S)-6-Acetyl-3-methyl-3-vinyl-cyclohexane-1,2-dicarboxylic acid 2-methyl ester 1-(2-thioxo-2H-pyridin-1-yl) ester

Guidance literature:: Multi-step reaction with 7 steps

1: 79 percent / Zn, Me₃Al / tetrahydrofuran / 20 °C

2: 83 percent / NaOMe / methanol / 50 °C

3: 80percent AcOH / 23 °C

4: NaIO₄, silica gel / H₂O; CH₂Cl₂

5: 78 percent / NaClO₂, NaH₂PO₄, MeCH=CMe₂ / H₂O; 2-methyl-propan-2-ol / 23 °C

6: (COCl)2, pyridine / benzene / 5 °C

7: DMAP / benzene / 5 to 25 deg C

With pyridine; dmap; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; trimethylaluminum; sodium methylate; silica gel; acetic acid; zinc; In tetrahydrofuran; methanol; dichloromethane; water; tert-butyl alcohol; benzene;
DOI:10.1016/S0040-4039(00)77678-7