Methyl <1(R)-(1α,4α,5β)>-5-<<(benzyloxy)methyl>oxy>-4-<<(bromomethyl)dimethylsilyl>oxy>-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-cyclohexene-1-carboxylate

Base Information

Chemical Name:Methyl <1(R)-(1α,4α,5β)>-5-<<(benzyloxy)methyl>oxy>-4-<<(bromomethyl)dimethylsilyl>oxy>-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-cyclohexene-1-carboxylate
CAS No.:160911-89-7
Molecular Formula:C₂₅H₄₁BrO₆Si₂
Molecular Weight:573.672
Hs Code.:

Methyl <1(R)-(1α,4α,5β)>-5-<<(benzyloxy)methyl>oxy>-4-<<(bromomethyl)dimethylsilyl>oxy>-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-cyclohexene-1-carboxylate

Synonyms:Methyl <1(R)-(1α,4α,5β)>-5-<<(benzyloxy)methyl>oxy>-4-<<(bromomethyl)dimethylsilyl>oxy>-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-cyclohexene-1-carboxylate

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Chemical Property of Methyl <1(R)-(1α,4α,5β)>-5-<<(benzyloxy)methyl>oxy>-4-<<(bromomethyl)dimethylsilyl>oxy>-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-cyclohexene-1-carboxylate

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Technology Process of Methyl <1(R)-(1α,4α,5β)>-5-<<(benzyloxy)methyl>oxy>-4-<<(bromomethyl)dimethylsilyl>oxy>-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-cyclohexene-1-carboxylate

There total 4 articles about Methyl <1(R)-(1α,4α,5β)>-5-<<(benzyloxy)methyl>oxy>-4-<<(bromomethyl)dimethylsilyl>oxy>-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-cyclohexene-1-carboxylate 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: 97.0%

: 16532-02-8
bromomethyldimethylsilyl chloride

: 160911-88-6
Methyl <1(R)-(1α,4α,5β)>-5-<<(benzyloxy)methyl>oxy>-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-4-hydroxy-2-cyclohexene-1-carboxylate

: 160911-89-7
Methyl <1(R)-(1α,4α,5β)>-5-<<(benzyloxy)methyl>oxy>-4-<<(bromomethyl)dimethylsilyl>oxy>-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-cyclohexene-1-carboxylate

Guidance literature:: With triethylamine; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1021/jo00102a025

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 160911-89-7
Methyl <1(R)-(1α,4α,5β)>-5-<<(benzyloxy)methyl>oxy>-4-<<(bromomethyl)dimethylsilyl>oxy>-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-cyclohexene-1-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: 97 percent / i-Pr₂NEt / CH₂Cl₂ / 15 h / Ambient temperature

2: 72 percent / MeONa / tetrahydrofuran; methanol / 0.25 h / Ambient temperature

3: 97 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

With sodium methylate; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jo00102a025

Reference yield:

: 105539-80-8
methyl<1(R)-(1α,4α,5β)>-4-(benzoyloxy)-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-5-hydroxy-2-cyclohexene-1-carboxylate

: 160911-89-7
Methyl <1(R)-(1α,4α,5β)>-5-<<(benzyloxy)methyl>oxy>-4-<<(bromomethyl)dimethylsilyl>oxy>-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-cyclohexene-1-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: 97 percent / i-Pr₂NEt / CH₂Cl₂ / 15 h / Ambient temperature

2: 72 percent / MeONa / tetrahydrofuran; methanol / 0.25 h / Ambient temperature

3: 97 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

With sodium methylate; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jo00102a025