(2R,3S,4S,6S)-4-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-((2S,3S)-3-vinyl-oxiranylmethyl)-tetrahydro-pyran-3-ol

Base Information

Chemical Name:(2R,3S,4S,6S)-4-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-((2S,3S)-3-vinyl-oxiranylmethyl)-tetrahydro-pyran-3-ol
CAS No.:221380-94-5
Molecular Formula:C₃₄H₄₂O₅Si
Molecular Weight:558.79
Hs Code.:

Synonyms:(2R,3S,4S,6S)-4-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-((2S,3S)-3-vinyl-oxiranylmethyl)-tetrahydro-pyran-3-ol

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Chemical Property of (2R,3S,4S,6S)-4-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-((2S,3S)-3-vinyl-oxiranylmethyl)-tetrahydro-pyran-3-ol

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Technology Process of (2R,3S,4S,6S)-4-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-((2S,3S)-3-vinyl-oxiranylmethyl)-tetrahydro-pyran-3-ol

There total 13 articles about (2R,3S,4S,6S)-4-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-((2S,3S)-3-vinyl-oxiranylmethyl)-tetrahydro-pyran-3-ol 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: 71.0%

: 221380-93-4
(2R,3S,4S,6S)-4-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-triethylsilanyloxy-2-((2S,3S)-3-vinyl-oxiranylmethyl)-tetrahydro-pyran

: (2R,3S,4S,6S)-4-Benzyloxy-6-hydroxymethyl-2-((2S,3S)-3-vinyl-oxiranylmethyl)-tetrahydro-pyran-3-ol

: 221380-94-5
(2R,3S,4S,6S)-4-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-((2S,3S)-3-vinyl-oxiranylmethyl)-tetrahydro-pyran-3-ol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at -20 - 0 ℃; for 1h; Yield given;
DOI:10.1002/(SICI)1521-3765(19990201)5:2<628::AID-CHEM628>3.0.CO;2-E

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: (2R,3S,4S,6S)-4-Benzyloxy-6-hydroxymethyl-2-((2S,3S)-3-vinyl-oxiranylmethyl)-tetrahydro-pyran-3-ol

: 221380-94-5
(2R,3S,4S,6S)-4-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-((2S,3S)-3-vinyl-oxiranylmethyl)-tetrahydro-pyran-3-ol

Guidance literature:: With 1H-imidazole; In dichloromethane; N,N-dimethyl-formamide; at 0 ℃; for 3h; Yield given;
DOI:10.1002/(SICI)1521-3765(19990201)5:2<628::AID-CHEM628>3.0.CO;2-E

Reference yield:

: 100-39-0
benzyl bromide

: 221380-94-5
(2R,3S,4S,6S)-4-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-((2S,3S)-3-vinyl-oxiranylmethyl)-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 10 steps

1: 1.) nBu₂SnO, 2.) nBu₄NBr / 1.) MeOH, 60 deg C, 1 h, 2.) C₆H₆, 80 deg C, 5 h

2: 95 percent / 2,6-lutidine / CH₂Cl₂ / 4 h / 0 °C

3: 1.) O₃, 2.) PPh₃ / 1.) CH₂Cl₂, -78 deg C, 2 h, 2.) CH₂Cl₂, 25 deg C, 18 h

4: benzene / 17 h / 25 °C

5: 100 percent / DIBAL / CH₂Cl₂ / 3 h / -78 °C

6: 89 percent / (+)-DET, Ti(iPrO)4, t-BuOOH, 4 Angstroem molecular sieves / CH₂Cl₂; 2,2,4-trimethyl-pentane / 19 h / -25 °C

7: Et₃N, SO₃*pyr / CH₂Cl₂; dimethylsulfoxide / 2 h

8: 1.) NaHMDS / 1.) THF, 0 deg C, 1 h, 2.) THF, 25 deg C, 1 h

9: TBAF / tetrahydrofuran / 1 h / -20 - 0 °C

10: imidazole / dimethylformamide; CH₂Cl₂ / 3 h / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; 4 A molecular sieve; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; sodium hexamethyldisilazane; diisobutylaluminium hydride; di(n-butyl)tin oxide; ozone; triethylamine; triphenylphosphine; In tetrahydrofuran; 2,2,4-trimethylpentane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;
DOI:10.1002/(SICI)1521-3765(19990201)5:2<628::AID-CHEM628>3.0.CO;2-E