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

Base Information

• Chemical Name: ethyl 6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxy-(1S,2S,6R)-3-cyclohexene-1-carboxylate
• CAS No.: 331005-74-4
• Molecular Formula: C₁₄H₂₂O₅
• Molecular Weight: 270.326
• Mol file: 331005-74-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about ethyl 6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxy-(1S,2S,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: 33.4%

ethyl 6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-oxo-(1RS,6R)-3-cyclohexene-1-carboxylate → ethyl 6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxy-(1S,2R,6R)-3-cyclohexene-1-carboxylate (331005-73-3) + ethyl 6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxy-(1S,2S,6R)-3-cyclohexene-1-carboxylate (331005-74-4) + ethyl 6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxy-(1R,2S,6R)-3-cyclohexene-1-carboxylate (331005-75-5)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; In ethanol; 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 6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxy-(1S,2S,6R)-3-cyclohexene-1-carboxylate (331005-74-4)

Guidance literature:

Multi-step reaction with 4 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: 16.5 percent / CeCl₃*7H₂O; NaBH₄ / ethanol / 1 h / 20 °C

With 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:

(2Z)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-en-1-ol (80532-35-0) → ethyl 6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxy-(1S,2S,6R)-3-cyclohexene-1-carboxylate (331005-74-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 65 percent / PDC / CH₂Cl₂ / 2 h / Heating

2: 68 percent / NaH; H₂ / tetrahydrofuran / 0.25 h / 50 °C

3: 16.5 percent / CeCl₃*7H₂O; NaBH₄ / ethanol / 1 h / 20 °C

With sodium tetrahydroborate; dipyridinium dichromate; cerium(III) chloride; hydrogen; sodium hydride; In tetrahydrofuran; ethanol; dichloromethane; 2: Michael-Wittig reaction;

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

upstream raw materials:

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

(2Z)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-en-1-ol

2,3-isopropylidene-glyceraldehyde

Downstream raw materials:

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

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