{(2S,3S)-3-[(2S,3R,4S)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-pentyl]-oxiranyl}-methanol

Base Information

Chemical Name:{(2S,3S)-3-[(2S,3R,4S)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-pentyl]-oxiranyl}-methanol
CAS No.:155300-01-9
Molecular Formula:C₂₃H₄₀O₄Si
Molecular Weight:408.654
Hs Code.:

Synonyms:{(2S,3S)-3-[(2S,3R,4S)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-pentyl]-oxiranyl}-methanol

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Chemical Property of {(2S,3S)-3-[(2S,3R,4S)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-pentyl]-oxiranyl}-methanol

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Technology Process of {(2S,3S)-3-[(2S,3R,4S)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-pentyl]-oxiranyl}-methanol

There total 10 articles about {(2S,3S)-3-[(2S,3R,4S)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-pentyl]-oxiranyl}-methanol 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: 87.0%

: 155300-00-8
(E)-(5S,6R,7S)-8-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-5,7-dimethyl-oct-2-en-1-ol

: 155300-01-9
{(2S,3S)-3-[(2S,3R,4S)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-pentyl]-oxiranyl}-methanol

Guidance literature:: With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate; 4 A molecular sieve; In dichloromethane; at -20 ℃;
DOI:10.1016/S0040-4039(00)76542-7

Reference yield:

: 106357-30-6
1-benzyloxy-2(S),4(S)-dimethyl-hex-5-en-3(R)-ol

: 155300-01-9
{(2S,3S)-3-[(2S,3R,4S)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-pentyl]-oxiranyl}-methanol

Guidance literature:: Multi-step reaction with 6 steps

1: 100 percent / Et₃N / CH₂Cl₂ / 0.5 h / -30 °C

2: 1.) 9-BBN, 2.) H₂O₂, NaOH / 1.) THF, reflux, 2 h, 2.) THF, H₂O, r.t., 1 h

3: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) CH₂Cl₂, -78 deg C, 15 min

4: 93 percent / i-Pr₂NEt, LiCl / acetonitrile / 20 h

5: 97 percent / DIBALH / tetrahydrofuran; toluene / 2 h / -78 °C

6: 80 percent / L-(+)-diethyl tartrate, t-BuOOH, Ti(OPr-i)4, 4 Angstroem molecular sieves / CH₂Cl₂; 2,2,4-trimethyl-pentane / 3.5 h / -20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; diethyl (2R,3R)-tartrate; 4 A molecular sieve; dihydrogen peroxide; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; In tetrahydrofuran; 2,2,4-trimethylpentane; dichloromethane; toluene; acetonitrile;
DOI:10.1039/a804170i

Reference yield:

: 155417-63-3
[(1R,2S)-1-((S)-2-Benzyloxy-1-methyl-ethyl)-2-methyl-but-3-enyloxy]-tert-butyl-dimethyl-silane

: 155300-01-9
{(2S,3S)-3-[(2S,3R,4S)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-pentyl]-oxiranyl}-methanol

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) 9-BBN, 2.) H₂O₂, NaOH / 1.) THF, reflux, 2 h, 2.) THF, H₂O, r.t., 1 h

2: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) CH₂Cl₂, -78 deg C, 15 min

3: 93 percent / i-Pr₂NEt, LiCl / acetonitrile / 20 h

4: 97 percent / DIBALH / tetrahydrofuran; toluene / 2 h / -78 °C

5: 80 percent / L-(+)-diethyl tartrate, t-BuOOH, Ti(OPr-i)4, 4 Angstroem molecular sieves / CH₂Cl₂; 2,2,4-trimethyl-pentane / 3.5 h / -20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; diethyl (2R,3R)-tartrate; 4 A molecular sieve; dihydrogen peroxide; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; In tetrahydrofuran; 2,2,4-trimethylpentane; dichloromethane; toluene; acetonitrile;
DOI:10.1039/a804170i