ethyl 2-acetoxy-6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-(1S,2R,6R)-3-cyclohexene-1-carboxylate

Base Information

• Chemical Name: ethyl 2-acetoxy-6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-(1S,2R,6R)-3-cyclohexene-1-carboxylate
• CAS No.: 331005-76-6
• Molecular Formula: C₁₆H₂₄O₆
• Molecular Weight: 312.363
• Mol file: 331005-76-6.mol

Synonyms:ethyl 2-acetoxy-6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-(1S,2R,6R)-3-cyclohexene-1-carboxylate

Chemical Property of ethyl 2-acetoxy-6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-(1S,2R,6R)-3-cyclohexene-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 2-acetoxy-6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-(1S,2R,6R)-3-cyclohexene-1-carboxylate

There total 6 articles about ethyl 2-acetoxy-6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-(1S,2R,6R)-3-cyclohexene-1-carboxylate 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: 100.0%

acetic anhydride (108-24-7) + ethyl 6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxy-(1S,2R,6R)-3-cyclohexene-1-carboxylate (331005-73-3) → ethyl 2-acetoxy-6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-(1S,2R,6R)-3-cyclohexene-1-carboxylate (331005-76-6)

Guidance literature:

With pyridine; dmap; at 20 ℃; for 1h;

DOI:10.1016/S0957-4166(00)00429-8

Reference yield:

ethyl (Z)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate (91926-90-8,917877-01-1) → ethyl 2-acetoxy-6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-(1S,2R,6R)-3-cyclohexene-1-carboxylate (331005-76-6)

Guidance literature:

Multi-step reaction with 5 steps

1: DIBAL-H / CH₂Cl₂

2: 65 percent / PDC / CH₂Cl₂ / 2 h / Heating

3: 68 percent / NaH; H₂ / tetrahydrofuran / 0.25 h / 50 °C

4: 33.4 percent / CeCl₃*7H₂O; NaBH₄ / ethanol / 1 h / 20 °C

5: 100 percent / pyridine; DMAP / 1 h / 20 °C

With pyridine; dmap; sodium tetrahydroborate; dipyridinium dichromate; cerium(III) chloride; hydrogen; sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran; ethanol; dichloromethane; 3: Michael-Wittig reaction;

DOI:10.1016/S0957-4166(00)00429-8

Reference yield:

cis-2,3-Didesoxy-4,5-O-isopropyliden-aldehydo-D-glycero-pent-2-enose (115509-80-3) → ethyl 2-acetoxy-6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-(1S,2R,6R)-3-cyclohexene-1-carboxylate (331005-76-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 68 percent / NaH; H₂ / tetrahydrofuran / 0.25 h / 50 °C

2: 33.4 percent / CeCl₃*7H₂O; NaBH₄ / ethanol / 1 h / 20 °C

3: 100 percent / pyridine; DMAP / 1 h / 20 °C

With pyridine; dmap; sodium tetrahydroborate; cerium(III) chloride; hydrogen; sodium hydride; In tetrahydrofuran; ethanol; 1: Michael-Wittig reaction;

DOI:10.1016/S0957-4166(00)00429-8

upstream raw materials:

acetic anhydride

ethyl 6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxy-(1S,2R,6R)-3-cyclohexene-1-carboxylate

ethyl (Z)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate

cis-2,3-Didesoxy-4,5-O-isopropyliden-aldehydo-D-glycero-pent-2-enose

Downstream raw materials:

ethyl 2-acetoxy-3,4-dihydroxy-6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-(1S,2S,3S,4S,6R)-cyclohexane-1-carboxylate