[3R-(1Z,3β,4α,5α)]-2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-hydroxy-2-methylenecyclohexylidene]ethyl trimethylacetate

Base Information

Chemical Name:[3R-(1Z,3β,4α,5α)]-2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-hydroxy-2-methylenecyclohexylidene]ethyl trimethylacetate
CAS No.:342644-90-0
Molecular Formula:C₂₆H₅₀O₅Si₂
Molecular Weight:498.851
Hs Code.:

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

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

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

There total 15 articles about [3R-(1Z,3β,4α,5α)]-2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-hydroxy-2-methylenecyclohexylidene]ethyl trimethylacetate 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: 98.0%

: [3R-(1Z,3α,4β,5β)]-2-(5-tert-butyldimethylsilyloxy-3,4-dihydroxy-2-methylenecyclohexylidene)ethyl trimethylacetate

: 18162-48-6
tert-butyldimethylsilyl chloride

: 342644-90-0
[3R-(1Z,3β,4α,5α)]-2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-hydroxy-2-methylenecyclohexylidene]ethyl trimethylacetate

Guidance literature:: With 1H-imidazole; In dichloromethane; at 0 ℃; for 11h; stereoselective reaction; Inert atmosphere;
DOI:10.1016/j.tet.2015.08.055

Reference yield: 96.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

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

: 342644-90-0
[3R-(1Z,3β,4α,5α)]-2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-hydroxy-2-methylenecyclohexylidene]ethyl trimethylacetate

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 0 ℃; for 3h;
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

: 342644-90-0
[3R-(1Z,3β,4α,5α)]-2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-hydroxy-2-methylenecyclohexylidene]ethyl trimethylacetate

Guidance literature:: Multi-step reaction with 3 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

With pyridine; 1H-imidazole; dmap; camphor-10-sulfonic acid; (+)-10-camphorsulfonic acid; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja003976k