(2S,4aR,5R,8aR)-N-benzyloxycarbonyl-2-propyl-5-methyl-decahydroquinolin-4-one-ethane-1,2-diyl dithioacetal

Base Information

• Chemical Name: (2S,4aR,5R,8aR)-N-benzyloxycarbonyl-2-propyl-5-methyl-decahydroquinolin-4-one-ethane-1,2-diyl dithioacetal
• CAS No.: 459410-94-7
• Molecular Formula: C₂₃H₃₃NO₂S₂
• Molecular Weight: 419.653
• Mol file: 459410-94-7.mol

Synonyms:(2S,4aR,5R,8aR)-N-benzyloxycarbonyl-2-propyl-5-methyl-decahydroquinolin-4-one-ethane-1,2-diyl dithioacetal

Chemical Property of (2S,4aR,5R,8aR)-N-benzyloxycarbonyl-2-propyl-5-methyl-decahydroquinolin-4-one-ethane-1,2-diyl dithioacetal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4aR,5R,8aR)-N-benzyloxycarbonyl-2-propyl-5-methyl-decahydroquinolin-4-one-ethane-1,2-diyl dithioacetal

There total 8 articles about (2S,4aR,5R,8aR)-N-benzyloxycarbonyl-2-propyl-5-methyl-decahydroquinolin-4-one-ethane-1,2-diyl dithioacetal 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: 64.0%

ethane-1,2-dithiol (540-63-6) + (2S,4aRS,5R,8aR)-N-benzyloxycarbonyl-2-propyl-5-methyl-decahydroquinolin-4-one → (2S,4aR,5R,8aR)-N-benzyloxycarbonyl-2-propyl-5-methyl-decahydroquinolin-4-one-ethane-1,2-diyl dithioacetal (459410-94-7)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 0 - 20 ℃; for 17h;

DOI:10.1007/s007060200030

Reference yield:

(2R)-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-2-(4-pentenyl)-5,6-didehydropiperidin-4-one (217447-15-9) → (2S,4aR,5R,8aR)-N-benzyloxycarbonyl-2-propyl-5-methyl-decahydroquinolin-4-one-ethane-1,2-diyl dithioacetal (459410-94-7)

Guidance literature:

Multi-step reaction with 7 steps

1: CuCl, BF₃*Et₂O / tetrahydrofuran / -78 °C

2: 75 percent / NaIO₄, K₂OsO₄ / H₂O; dioxane

3: 81 percent / NaOH, dibenzo-18-cr.-6 / benzene

4: 1.) Me₃SiCl; 2.) TBAF / 1.) THF, -78 deg C

5: HCl / H₂O; methanol

6: NaHCO₃

7: BF₃*Et₂O

With hydrogenchloride; sodium hydroxide; potassium osmate(VI); sodium periodate; dibenzo-18-crown-6; chloro-trimethyl-silane; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; copper(l) chloride; In tetrahydrofuran; 1,4-dioxane; methanol; water; benzene;

DOI:10.1016/S0040-4039(98)01745-6

Reference yield:

2,2-Dimethyl-propionic acid (2R,3R,4S,5S,6R)-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-2-((2R,6S)-4-oxo-2-pent-4-enyl-6-propyl-piperidin-1-yl)-tetrahydro-pyran-3-yl ester (217447-16-0) → (2S,4aR,5R,8aR)-N-benzyloxycarbonyl-2-propyl-5-methyl-decahydroquinolin-4-one-ethane-1,2-diyl dithioacetal (459410-94-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 75 percent / NaIO₄, K₂OsO₄ / H₂O; dioxane

2: 81 percent / NaOH, dibenzo-18-cr.-6 / benzene

3: 1.) Me₃SiCl; 2.) TBAF / 1.) THF, -78 deg C

4: HCl / H₂O; methanol

5: NaHCO₃

6: BF₃*Et₂O

With hydrogenchloride; sodium hydroxide; potassium osmate(VI); sodium periodate; dibenzo-18-crown-6; chloro-trimethyl-silane; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; In 1,4-dioxane; methanol; water; benzene;

DOI:10.1016/S0040-4039(98)01745-6

upstream raw materials:

ethane-1,2-dithiol

(2S,4aR,5R,8aR)-N-benzyloxycarbonyl-2-propyl-5-methyl-decahydroquinolin-4-one

(2S,4aR,5R,8aR)-5-Methyl-2-propyl-octahydro-quinolin-4-one

(2R)-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-2-(4-pentenyl)-5,6-didehydropiperidin-4-one