(5S,6S,1'R^*,2'R)-5-<(1-ethoxyethoxy)methyl>-6-(1'-hydroxy-3'-methyl-2'-phenylselenobutyl)-2-cyclohexen-1-one

Base Information

• Chemical Name: (5S,6S,1'R^*,2'R)-5-<(1-ethoxyethoxy)methyl>-6-(1'-hydroxy-3'-methyl-2'-phenylselenobutyl)-2-cyclohexen-1-one
• CAS No.: 123453-96-3
• Molecular Formula: C₂₂H₃₂O₄Se
• Molecular Weight: 439.454

Synonyms:(5S,6S,1'R^*,2'R)-5-<(1-ethoxyethoxy)methyl>-6-(1'-hydroxy-3'-methyl-2'-phenylselenobutyl)-2-cyclohexen-1-one

Chemical Property of (5S,6S,1'R^*,2'R)-5-<(1-ethoxyethoxy)methyl>-6-(1'-hydroxy-3'-methyl-2'-phenylselenobutyl)-2-cyclohexen-1-one

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Technology Process of (5S,6S,1'R^*,2'R)-5-<(1-ethoxyethoxy)methyl>-6-(1'-hydroxy-3'-methyl-2'-phenylselenobutyl)-2-cyclohexen-1-one

There total 18 articles about (5S,6S,1'R^*,2'R)-5-<(1-ethoxyethoxy)methyl>-6-(1'-hydroxy-3'-methyl-2'-phenylselenobutyl)-2-cyclohexen-1-one 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:

(1S)-3-cyclohexenecarboxylic acid (5708-19-0) → (5S,6S,1'R*,2'R)-5-<(1-ethoxyethoxy)methyl>-6-(1'-hydroxy-3'-methyl-2'-phenylselenobutyl)-2-cyclohexen-1-one (123453-96-3)

Guidance literature:

Multi-step reaction with 6 steps

1: KI-I₂, 0.5 m aq. NaHCO₃ / CH₂Cl₂; H₂O / 16 h

2: DBU / benzene / 8 h / Heating

3: LiAlH₄ / tetrahydrofuran / 1 h / Ambient temperature

4: MnO₂ / CHCl₃ / 26 h / Ambient temperature

5: 98.6 percent / PPTS / CH₂Cl₂ / Ambient temperature

6: 1) LDA / 1) -10 deg C to -5 deg C, 20 min, 2) -78 deg C

With manganese(IV) oxide; lithium aluminium tetrahydride; iodine; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; potassium iodide; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; chloroform; water; benzene;

DOI:10.1016/S0040-4020(01)81464-2

Reference yield:

(1S,4S,5S)-4-iodo-6-oxabicyclo<3.2.1>octan-7-one (123536-66-3) → (5S,6S,1'R*,2'R)-5-<(1-ethoxyethoxy)methyl>-6-(1'-hydroxy-3'-methyl-2'-phenylselenobutyl)-2-cyclohexen-1-one (123453-96-3)

Guidance literature:

Multi-step reaction with 5 steps

1: DBU / benzene / 8 h / Heating

2: LiAlH₄ / tetrahydrofuran / 1 h / Ambient temperature

3: MnO₂ / CHCl₃ / 26 h / Ambient temperature

4: 98.6 percent / PPTS / CH₂Cl₂ / Ambient temperature

5: 1) LDA / 1) -10 deg C to -5 deg C, 20 min, 2) -78 deg C

With manganese(IV) oxide; lithium aluminium tetrahydride; pyridinium p-toluenesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; chloroform; benzene;

DOI:10.1016/S0040-4020(01)81464-2

Reference yield:

(5S)-5-hydroxymethyl-2-cyclohexen-1-one (123536-65-2) → (5S,6S,1'R*,2'R)-5-<(1-ethoxyethoxy)methyl>-6-(1'-hydroxy-3'-methyl-2'-phenylselenobutyl)-2-cyclohexen-1-one (123453-96-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 98.6 percent / PPTS / CH₂Cl₂ / Ambient temperature

2: 1) LDA / 1) -10 deg C to -5 deg C, 20 min, 2) -78 deg C

With pyridinium p-toluenesulfonate; lithium diisopropyl amide; In dichloromethane;

DOI:10.1016/S0040-4020(01)81464-2

upstream raw materials:

3-methyl-2-(phenylseleno)butyraldehyde

(5S)-5-<(1-ethoxyethoxy)methyl>-2-cyclohexen-1-one

(1S)-3-cyclohexenecarboxylic acid

diphenyl diselenide

Downstream raw materials:

(3S,8R,9R,10S)-(-)-periplanone-B

(1S,5S,6R,1'Z)-5-<(1-ethoxyethoxy)methyl>-6-(3'-methyl-1'-butenyl)-1-vinyl-2-cyclohexen-1-ol

(4S,5E,7S,9R,10R)-9,10-epoxy-4-isopropyl-7-<(o-nitrophenyl)selenomethyl>-5-cyclodecen-1-one

(5S,6R,1'Z)-5-<(1-ethoxyethoxy)methyl>-6-(3'-methyl-1'-butenyl)-2-cyclohexen-1-one

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