[3R-(1Z,3β,4α,5α)]-2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-(3-hydroxypropoxy)-2-methylenecyclohexylidene]-1-chloroethane

Base Information

Chemical Name:[3R-(1Z,3β,4α,5α)]-2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-(3-hydroxypropoxy)-2-methylenecyclohexylidene]-1-chloroethane
CAS No.:342645-82-3
Molecular Formula:C₂₄H₄₇ClO₄Si₂
Molecular Weight:491.259
Hs Code.:

Synonyms:[3R-(1Z,3β,4α,5α)]-2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-(3-hydroxypropoxy)-2-methylenecyclohexylidene]-1-chloroethane

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Chemical Property of [3R-(1Z,3β,4α,5α)]-2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-(3-hydroxypropoxy)-2-methylenecyclohexylidene]-1-chloroethane

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Technology Process of [3R-(1Z,3β,4α,5α)]-2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-(3-hydroxypropoxy)-2-methylenecyclohexylidene]-1-chloroethane

There total 6 articles about [3R-(1Z,3β,4α,5α)]-2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-(3-hydroxypropoxy)-2-methylenecyclohexylidene]-1-chloroethane 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: 57.0%

: 342644-91-1
[3R-(1Z,3β,4α,5α)]-2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-(3-hydroxypropoxy)-2-methylenecyclohexylidene]ethanol

: 342645-82-3
[3R-(1Z,3β,4α,5α)]-2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-(3-hydroxypropoxy)-2-methylenecyclohexylidene]-1-chloroethane

Guidance literature:: With N-chloro-succinimide; dimethylsulfide; In dichloromethane; for 0.666667h;
DOI:10.1021/ja003976k

Reference yield:

: 244278-87-3
[3R-(1Z,3β,4α,5α)]-2-[5-(1,1-dimethylethyl)dimethylsilyloxy-3,4-isopropylidenedioxy-2-methylenecyclohexylidene]ethanol

: 342645-82-3
[3R-(1Z,3β,4α,5α)]-2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-(3-hydroxypropoxy)-2-methylenecyclohexylidene]-1-chloroethane

Guidance literature:: Multi-step reaction with 6 steps

1: 83 percent / pyridine; DMAP / CH₂Cl₂ / 1 h / 0 °C

2: 82 percent / CSA; (+)-10-camphorsulfonic acid / methanol / 3 h / 20 °C

3: 96 percent / imidazole / dimethylformamide / 3 h / 0 °C

4: 88 percent / Me₄NOH; aq. NaOH / toluene / 72 h / 20 °C

5: 91 percent / LiAlH₄ / tetrahydrofuran / 0.25 h / 0 °C

6: 57 percent / NCS; Me₂S / CH₂Cl₂ / 0.67 h

With pyridine; 1H-imidazole; dmap; sodium hydroxide; N-chloro-succinimide; lithium aluminium tetrahydride; dimethylsulfide; camphor-10-sulfonic acid; tetramethyl ammoniumhydroxide; (+)-10-camphorsulfonic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 4: Michael addition;
DOI:10.1021/ja003976k

Reference yield:

: 377091-68-4
[3R-(1Z,3β,4α,5α)]-2-[3,4,5-trihydroxy-2-methylenecyclohexylidene]ethyl trimethylacetate

: 342645-82-3
[3R-(1Z,3β,4α,5α)]-2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-(3-hydroxypropoxy)-2-methylenecyclohexylidene]-1-chloroethane

Guidance literature:: Multi-step reaction with 4 steps

1: 96 percent / imidazole / dimethylformamide / 3 h / 0 °C

2: 88 percent / Me₄NOH; aq. NaOH / toluene / 72 h / 20 °C

3: 91 percent / LiAlH₄ / tetrahydrofuran / 0.25 h / 0 °C

4: 57 percent / NCS; Me₂S / CH₂Cl₂ / 0.67 h

With 1H-imidazole; sodium hydroxide; N-chloro-succinimide; lithium aluminium tetrahydride; dimethylsulfide; tetramethyl ammoniumhydroxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; 2: Michael addition;
DOI:10.1021/ja003976k