(4aS,6S,8aR)-6-((E)-5-Benzenesulfonyl-pent-4-enyl)-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyridine-5-carboxylic acid 2,2,2-trichloro-ethyl ester

Base Information

• Chemical Name: (4aS,6S,8aR)-6-((E)-5-Benzenesulfonyl-pent-4-enyl)-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyridine-5-carboxylic acid 2,2,2-trichloro-ethyl ester
• CAS No.: 179536-76-6
• Molecular Formula: C₂₃H₃₀Cl₃NO₆S
• Molecular Weight: 554.919
• Mol file: 179536-76-6.mol

Synonyms:(4aS,6S,8aR)-6-((E)-5-Benzenesulfonyl-pent-4-enyl)-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyridine-5-carboxylic acid 2,2,2-trichloro-ethyl ester

Chemical Property of (4aS,6S,8aR)-6-((E)-5-Benzenesulfonyl-pent-4-enyl)-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyridine-5-carboxylic acid 2,2,2-trichloro-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4aS,6S,8aR)-6-((E)-5-Benzenesulfonyl-pent-4-enyl)-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyridine-5-carboxylic acid 2,2,2-trichloro-ethyl ester

There total 7 articles about (4aS,6S,8aR)-6-((E)-5-Benzenesulfonyl-pent-4-enyl)-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyridine-5-carboxylic acid 2,2,2-trichloro-ethyl 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:

diethyl phenylsulfonylmethylphosphonate (56069-39-7) + (4aS,6S,8aR)-2,2-Dimethyl-6-(4-oxo-butyl)-hexahydro-[1,3]dioxino[5,4-b]pyridine-5-carboxylic acid 2,2,2-trichloro-ethyl ester (1054652-01-5) → (4aS,6S,8aR)-6-((E)-5-Benzenesulfonyl-pent-4-enyl)-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyridine-5-carboxylic acid 2,2,2-trichloro-ethyl ester (179536-76-6)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1016/S0040-4020(99)00996-5

Reference yield:

2-((4aS,6R,8aR)-5-Benzyl-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyridin-6-yl)-ethanol (179536-73-3) → (4aS,6S,8aR)-6-((E)-5-Benzenesulfonyl-pent-4-enyl)-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyridine-5-carboxylic acid 2,2,2-trichloro-ethyl ester (179536-76-6)

Guidance literature:

Multi-step reaction with 7 steps

1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

2: 338 mg / NaH / tetrahydrofuran / 40 h / 20 °C

3: H₂ / Pd(OH)2 / ethanol / 15 h / 760 Torr

4: LiAlH₄ / tetrahydrofuran / 12 h / Heating

5: 220 mg / K₂CO₃ / CHCl₃; H₂O / 8 h / 20 °C

6: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

7: 266 mg / NaH / tetrahydrofuran / 3 h / 20 °C

With lithium aluminium tetrahydride; oxalyl dichloride; hydrogen; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; palladium dihydroxide; In tetrahydrofuran; ethanol; dichloromethane; chloroform; water; 1: Oxidation / 2: Wittig-Horner reaction / 3: Hydrogenation / 4: Reduction / 5: Acylation / 6: Oxidation / 7: Wittig-Horner reaction;

DOI:10.1016/S0040-4020(99)00996-5

Reference yield:

ethyl (4aS,6R,8aR)-(+)-hexahydro-2,2-dimethyl-5-(phenylmethyl)-4H-1,3-dioxino-[5,4-b]pyridine-6-but-(2E)-enoate (179536-74-4) → (4aS,6S,8aR)-6-((E)-5-Benzenesulfonyl-pent-4-enyl)-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyridine-5-carboxylic acid 2,2,2-trichloro-ethyl ester (179536-76-6)

Guidance literature:

Multi-step reaction with 5 steps

1: H₂ / Pd(OH)2 / ethanol / 15 h / 760 Torr

2: LiAlH₄ / tetrahydrofuran / 12 h / Heating

3: 220 mg / K₂CO₃ / CHCl₃; H₂O / 8 h / 20 °C

4: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

5: 266 mg / NaH / tetrahydrofuran / 3 h / 20 °C

With lithium aluminium tetrahydride; oxalyl dichloride; hydrogen; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; palladium dihydroxide; In tetrahydrofuran; ethanol; dichloromethane; chloroform; water; 1: Hydrogenation / 2: Reduction / 3: Acylation / 4: Oxidation / 5: Wittig-Horner reaction;

DOI:10.1016/S0040-4020(99)00996-5

upstream raw materials:

diethyl phenylsulfonylmethylphosphonate

(4aS,6S,8aR)-2,2-Dimethyl-6-(4-oxo-butyl)-hexahydro-[1,3]dioxino[5,4-b]pyridine-5-carboxylic acid 2,2,2-trichloro-ethyl ester

2-((4aS,6R,8aR)-5-Benzyl-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyridin-6-yl)-ethanol

ethyl (4aS,6R,8aR)-(+)-hexahydro-2,2-dimethyl-5-(phenylmethyl)-4H-1,3-dioxino-[5,4-b]pyridine-6-but-(2E)-enoate

Downstream raw materials:

(4aS,5S,8aS,10aR)-5-Benzenesulfonylmethyl-2,2-dimethyl-decahydro-1,3-dioxa-4b-aza-phenanthrene