{(R)-1-Benzyloxymethyl-3-[(2R,3R)-3-(2,2-dibromo-vinyl)-3-methyl-oxiranyl]-propoxy}-tert-butyl-dimethyl-silane

Base Information

Chemical Name:{(R)-1-Benzyloxymethyl-3-[(2R,3R)-3-(2,2-dibromo-vinyl)-3-methyl-oxiranyl]-propoxy}-tert-butyl-dimethyl-silane
CAS No.:240133-63-5
Molecular Formula:C₂₂H₃₄Br₂O₃Si
Molecular Weight:534.404
Hs Code.:

Synonyms:{(R)-1-Benzyloxymethyl-3-[(2R,3R)-3-(2,2-dibromo-vinyl)-3-methyl-oxiranyl]-propoxy}-tert-butyl-dimethyl-silane

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Chemical Property of {(R)-1-Benzyloxymethyl-3-[(2R,3R)-3-(2,2-dibromo-vinyl)-3-methyl-oxiranyl]-propoxy}-tert-butyl-dimethyl-silane

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of {(R)-1-Benzyloxymethyl-3-[(2R,3R)-3-(2,2-dibromo-vinyl)-3-methyl-oxiranyl]-propoxy}-tert-butyl-dimethyl-silane

There total 10 articles about {(R)-1-Benzyloxymethyl-3-[(2R,3R)-3-(2,2-dibromo-vinyl)-3-methyl-oxiranyl]-propoxy}-tert-butyl-dimethyl-silane 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: 91.0%

: 558-13-4
carbon tetrabromide

: 240133-70-4
(2S,3R)-3-[(R)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-butyl]-2-methyl-oxirane-2-carbaldehyde

: 240133-63-5
{(R)-1-Benzyloxymethyl-3-[(2R,3R)-3-(2,2-dibromo-vinyl)-3-methyl-oxiranyl]-propoxy}-tert-butyl-dimethyl-silane

Guidance literature:: carbon tetrabromide; With triphenylphosphine; In dichloromethane; at 0 ℃; for 0.333333h;

(2S,3R)-3-[(R)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-butyl]-2-methyl-oxirane-2-carbaldehyde; With triethylamine; In dichloromethane; at -78 ℃; for 0.866667h; Further stages.;
DOI:10.1021/ja000001r

Reference yield:

: 52813-63-5
(5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone

: 240133-63-5
{(R)-1-Benzyloxymethyl-3-[(2R,3R)-3-(2,2-dibromo-vinyl)-3-methyl-oxiranyl]-propoxy}-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 8 steps

1.1: 63 percent / TfOH / CH₂Cl₂; pentane / 30 h / 0 °C

2.1: DIBAL / toluene / 1 h / -78 °C

3.1: 2.04 g / benzene / 2 h / Heating

4.1: 95 percent / imidazole / dimethylformamide / 3 h / 20 °C

5.1: 72 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C

6.1: 86 percent / (-)-D-diethyl tartrate; Ti(O-i-Pr)4; tert-butylhydroperoxide / CH₂Cl₂; decane / 5 h / -23 °C

7.1: 92 percent / Et₃N; SO₃*pyridine / CH₂Cl₂; dimethylsulfoxide / 4 h / 0 °C

8.1: PPh₃ / CH₂Cl₂ / 0.33 h / 0 °C

8.2: 91 percent / Et₃N / CH₂Cl₂ / 0.75 h / -78 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; pyridine-SO₃ complex; diethyl (2S,3S)-tartrate; trifluorormethanesulfonic acid; diisobutylaluminium hydride; triethylamine; triphenylphosphine; In decane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; pentane; benzene; 6.1: Sharpless asymmetric epoxidation;
DOI:10.1021/ol990648k

Reference yield:

: 77697-15-5
(R)-(-)-γ-benzyloxymethyl-γ-butyrolactone

: 240133-63-5
{(R)-1-Benzyloxymethyl-3-[(2R,3R)-3-(2,2-dibromo-vinyl)-3-methyl-oxiranyl]-propoxy}-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 7 steps

1.1: DIBAL / toluene / 1 h / -78 °C

2.1: 2.04 g / benzene / 2 h / Heating

3.1: 95 percent / imidazole / dimethylformamide / 3 h / 20 °C

4.1: 72 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C

5.1: 86 percent / (-)-D-diethyl tartrate; Ti(O-i-Pr)4; tert-butylhydroperoxide / CH₂Cl₂; decane / 5 h / -23 °C

6.1: 92 percent / Et₃N; SO₃*pyridine / CH₂Cl₂; dimethylsulfoxide / 4 h / 0 °C

7.1: PPh₃ / CH₂Cl₂ / 0.33 h / 0 °C

7.2: 91 percent / Et₃N / CH₂Cl₂ / 0.75 h / -78 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; pyridine-SO₃ complex; diethyl (2S,3S)-tartrate; diisobutylaluminium hydride; triethylamine; triphenylphosphine; In decane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; benzene; 5.1: Sharpless asymmetric epoxidation;
DOI:10.1021/ol990648k