(R)-2-((2R,6S,7S)-7-Methyl-4,4-dioxo-7a-phenylsulfanyl-6-propyl-hexahydro-1,5-dioxa-4λ⁶-thia-inden-2-yl)-propionic acid methyl ester

Base Information

• Chemical Name: (R)-2-((2R,6S,7S)-7-Methyl-4,4-dioxo-7a-phenylsulfanyl-6-propyl-hexahydro-1,5-dioxa-4λ⁶-thia-inden-2-yl)-propionic acid methyl ester
• CAS No.: 870452-53-2
• Molecular Formula: C₂₀H₂₈O₆S₂
• Molecular Weight: 428.571

Synonyms:(R)-2-((2R,6S,7S)-7-Methyl-4,4-dioxo-7a-phenylsulfanyl-6-propyl-hexahydro-1,5-dioxa-4λ⁶-thia-inden-2-yl)-propionic acid methyl ester

Chemical Property of (R)-2-((2R,6S,7S)-7-Methyl-4,4-dioxo-7a-phenylsulfanyl-6-propyl-hexahydro-1,5-dioxa-4λ⁶-thia-inden-2-yl)-propionic acid methyl ester

Chemical Property:

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Technology Process of (R)-2-((2R,6S,7S)-7-Methyl-4,4-dioxo-7a-phenylsulfanyl-6-propyl-hexahydro-1,5-dioxa-4λ⁶-thia-inden-2-yl)-propionic acid methyl ester

There total 2 articles about (R)-2-((2R,6S,7S)-7-Methyl-4,4-dioxo-7a-phenylsulfanyl-6-propyl-hexahydro-1,5-dioxa-4λ⁶-thia-inden-2-yl)-propionic 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: 79.0%

(R)-2-((2R,6S,7S)-7a-Hydroxy-7-methyl-4,4-dioxo-6-propyl-hexahydro-1,5-dioxa-4λ6-thia-inden-2-yl)-propionic acid methyl ester (870452-52-1) + thiophenol (108-98-5) → (R)-2-((2R,6S,7S)-7-Methyl-4,4-dioxo-7a-phenylsulfanyl-6-propyl-hexahydro-1,5-dioxa-4λ6-thia-inden-2-yl)-propionic acid methyl ester (870452-53-2)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃;

DOI:10.1002/anie.200501511

Reference yield:

4,6-dimethyl-1,1-dioxo-3-propyl-3,4,6,7,8,8a-hexahydro-1H-1λ6-benzo[c][1,2]oxathiin-7-ol → (R)-2-((2R,6S,7S)-7-Methyl-4,4-dioxo-7a-phenylsulfanyl-6-propyl-hexahydro-1,5-dioxa-4λ6-thia-inden-2-yl)-propionic acid methyl ester (870452-53-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: ozone; NaHCO₃ / CH₂Cl₂ / -78 °C

1.2: 87 percent / acetic anhydride; pyridine / CH₂Cl₂ / Heating

2.1: 79 percent / BF₃*Et₂O / CH₂Cl₂ / 20 °C

With boron trifluoride diethyl etherate; sodium hydrogencarbonate; ozone; In dichloromethane;

DOI:10.1002/anie.200501511

Reference yield:

(R)-2-((2R,6S,7S)-7-Methyl-4,4-dioxo-7a-phenylsulfanyl-6-propyl-hexahydro-1,5-dioxa-4λ6-thia-inden-2-yl)-propionic acid methyl ester (870452-53-2) → (S)-2-[(2R,5S)-5-((1S,2S)-2-Hydroxy-1-methyl-pentyl)-tetrahydro-furan-2-yl]-propionic acid benzyl ester (870452-47-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 59 percent / H₂ / Raney Ni / ethanol / 20 °C / 37503 Torr

2.1: 100 percent / sodium hydroxide / 20 °C

3.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 20 °C

3.2: 65 percent / 4-(N,N-dimethylamino)pyridine / toluene / Heating

4.1: 59 percent / PhCH₂OLi / tetrahydrofuran / 20 °C

With sodium hydroxide; 2,4,6-trichlorobenzoyl chloride; lithium benzyloxide; hydrogen; triethylamine; nickel; In tetrahydrofuran; ethanol; 3.1: Yamaguchi lactonization;

DOI:10.1002/anie.200501511

upstream raw materials:

(R)-2-((2R,6S,7S)-7a-Hydroxy-7-methyl-4,4-dioxo-6-propyl-hexahydro-1,5-dioxa-4λ⁶-thia-inden-2-yl)-propionic acid methyl ester

thiophenol

Downstream raw materials:

(1S,2S,5S,6R,7R)-2,6-Dimethyl-5-propyl-4,10-dioxa-bicyclo[5.2.1]decan-3-one

(S)-2-[(2R,5S)-5-((1S,2S)-2-Hydroxy-1-methyl-pentyl)-tetrahydro-furan-2-yl]-propionic acid benzyl ester

2-(5-{2-[2-(5-{3-[5-(2-dimethylamino-pentyl)-tetrahydro-furan-2-yl]-2-hydroxy-1-methyl-butyl}-tetrahydro-furan-2-yl)-propionyloxy]-1-methyl-pentyl}-tetrahydro-furan-2-yl)-propionic acid benzyl ester

2-(5-{2-[2-(5-{3-[5-(2-dimethylamino-pentyl)-tetrahydro-furan-2-yl]-2-hydroxy-1-methyl-butyl}-tetrahydro-furan-2-yl)-propionyloxy]-1-methyl-pentyl}-tetrahydro-furan-2-yl)-propionic acid benzyl ester

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