(3E)(5R)-6-[(2R,3R,5S)-3-tert-butyldimethylsiloxy-5-tert-butyldiphenylsiloxymethyloxolan-2-yl]-1-(4-methoxyphenylmethoxy)-5-phenylmethoxymethylhex-3-ene

Base Information

Chemical Name:(3E)(5R)-6-[(2R,3R,5S)-3-tert-butyldimethylsiloxy-5-tert-butyldiphenylsiloxymethyloxolan-2-yl]-1-(4-methoxyphenylmethoxy)-5-phenylmethoxymethylhex-3-ene
CAS No.:667421-79-6
Molecular Formula:C₄₉H₆₈O₆Si₂
Molecular Weight:809.246
Hs Code.:

(3E)(5R)-6-[(2R,3R,5S)-3-tert-butyldimethylsiloxy-5-tert-butyldiphenylsiloxymethyloxolan-2-yl]-1-(4-methoxyphenylmethoxy)-5-phenylmethoxymethylhex-3-ene

Synonyms:(3E)(5R)-6-[(2R,3R,5S)-3-tert-butyldimethylsiloxy-5-tert-butyldiphenylsiloxymethyloxolan-2-yl]-1-(4-methoxyphenylmethoxy)-5-phenylmethoxymethylhex-3-ene

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Chemical Property of (3E)(5R)-6-[(2R,3R,5S)-3-tert-butyldimethylsiloxy-5-tert-butyldiphenylsiloxymethyloxolan-2-yl]-1-(4-methoxyphenylmethoxy)-5-phenylmethoxymethylhex-3-ene

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Technology Process of (3E)(5R)-6-[(2R,3R,5S)-3-tert-butyldimethylsiloxy-5-tert-butyldiphenylsiloxymethyloxolan-2-yl]-1-(4-methoxyphenylmethoxy)-5-phenylmethoxymethylhex-3-ene

There total 20 articles about (3E)(5R)-6-[(2R,3R,5S)-3-tert-butyldimethylsiloxy-5-tert-butyldiphenylsiloxymethyloxolan-2-yl]-1-(4-methoxyphenylmethoxy)-5-phenylmethoxymethylhex-3-ene 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:

: 667421-82-1
methyl (3S)-4-tert-butyldiphenylsiloxy-3-triethylsiloxybutanoate

: 667421-79-6
(3E)(5R)-6-[(2R,3R,5S)-3-tert-butyldimethylsiloxy-5-tert-butyldiphenylsiloxymethyloxolan-2-yl]-1-(4-methoxyphenylmethoxy)-5-phenylmethoxymethylhex-3-ene

Guidance literature:: Multi-step reaction with 14 steps

1.1: DIBAL-H / toluene / 1 h / -78 °C

1.2: 94 percent / benzene / 8 h / 20 °C

2.1: 95 percent / DIBAL-H / CH₂Cl₂; toluene / 0.17 h / -78 °C

3.1: 90 percent / Ti(Oi-Pr)4; (-)-diethyl-D-tartrate; TBHP / CH₂Cl₂; 2,2,4-trimethyl-pentane / 5 h / -20 °C

4.1: DMSO; Et₃N; SO₃*Py / CH₂Cl₂ / 2 h / 20 °C

4.2: 79 percent / benzene / 8 h / 20 °C

5.1: 82 percent / CSA / methanol / 0.08 h / 0 °C

6.1: 90 percent / Ph₃P; Pd₂(dba)3*CHCl₃ / CH₂Cl₂ / 0.08 h / 20 °C

7.1: 86 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

8.1: hydrogen / Pd-C / ethanol / 2 h / 20 °C

9.1: 8.82 g / LiOH*H₂O / H₂O; methanol; tetrahydrofuran / 2 h / 20 °C

10.1: PivCl; Et₃N / tetrahydrofuran / 0.75 h / 0 °C

10.2: 88 percent / LiCl / tetrahydrofuran / 2 h / 20 °C

11.1: LHMDS / tetrahydrofuran / 0.75 h / -78 °C

11.2: 78 percent / LiI / tetrahydrofuran / 1 h / -50 °C

12.1: 91 percent / LiBH₄ / ethanol; tetrahydrofuran; H₂O / 2 h / 0 °C

13.1: tetra-n-propylammonium perruthenate; NMO; MS₄Angstroem / CH₂Cl₂

14.1: LMHDS / tetrahydrofuran / 1 h / -78 °C

14.2: 0.93 g / -78 °C

With 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; lithium hydroxide; lithium borohydride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; pyridine-SO₃ complex; diethyl (2S,3S)-tartrate; MS₄Angstroem; camphor-10-sulfonic acid; hydrogen; pivaloyl chloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; ethanol; dichloromethane; water; toluene; 1.2: Wittig reaction / 3.1: Sharpless asymmetric epoxydation / 4.2: Wittig reaction / 14.2: Julia olefination;
DOI:10.3987/com-03-9952

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 667421-79-6
(3E)(5R)-6-[(2R,3R,5S)-3-tert-butyldimethylsiloxy-5-tert-butyldiphenylsiloxymethyloxolan-2-yl]-1-(4-methoxyphenylmethoxy)-5-phenylmethoxymethylhex-3-ene

Guidance literature:: Multi-step reaction with 15 steps

1.1: imidazole / dimethylformamide / 0.33 h / 20 °C

1.2: 95 percent / imidazole / dimethylformamide / 0.33 h / 0 °C

2.1: DIBAL-H / toluene / 1 h / -78 °C

2.2: 94 percent / benzene / 8 h / 20 °C

3.1: 95 percent / DIBAL-H / CH₂Cl₂; toluene / 0.17 h / -78 °C

4.1: 90 percent / Ti(Oi-Pr)4; (-)-diethyl-D-tartrate; TBHP / CH₂Cl₂; 2,2,4-trimethyl-pentane / 5 h / -20 °C

5.1: DMSO; Et₃N; SO₃*Py / CH₂Cl₂ / 2 h / 20 °C

5.2: 79 percent / benzene / 8 h / 20 °C

6.1: 82 percent / CSA / methanol / 0.08 h / 0 °C

7.1: 90 percent / Ph₃P; Pd₂(dba)3*CHCl₃ / CH₂Cl₂ / 0.08 h / 20 °C

8.1: 86 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

9.1: hydrogen / Pd-C / ethanol / 2 h / 20 °C

10.1: 8.82 g / LiOH*H₂O / H₂O; methanol; tetrahydrofuran / 2 h / 20 °C

11.1: PivCl; Et₃N / tetrahydrofuran / 0.75 h / 0 °C

11.2: 88 percent / LiCl / tetrahydrofuran / 2 h / 20 °C

12.1: LHMDS / tetrahydrofuran / 0.75 h / -78 °C

12.2: 78 percent / LiI / tetrahydrofuran / 1 h / -50 °C

13.1: 91 percent / LiBH₄ / ethanol; tetrahydrofuran; H₂O / 2 h / 0 °C

14.1: tetra-n-propylammonium perruthenate; NMO; MS₄Angstroem / CH₂Cl₂

15.1: LMHDS / tetrahydrofuran / 1 h / -78 °C

15.2: 0.93 g / -78 °C

With 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; lithium hydroxide; lithium borohydride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; pyridine-SO₃ complex; diethyl (2S,3S)-tartrate; MS₄Angstroem; camphor-10-sulfonic acid; hydrogen; pivaloyl chloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; 2.2: Wittig reaction / 4.1: Sharpless asymmetric epoxydation / 5.2: Wittig reaction / 15.2: Julia olefination;
DOI:10.3987/com-03-9952

Reference yield:

: 667421-80-9
methyl (2E)-3-[(2R,3R,5S)-5-tert-butyldiphenylsiloxymethyl-3-hydroxyoxolan-2-yl]prop-2-enoate

: 667421-79-6
(3E)(5R)-6-[(2R,3R,5S)-3-tert-butyldimethylsiloxy-5-tert-butyldiphenylsiloxymethyloxolan-2-yl]-1-(4-methoxyphenylmethoxy)-5-phenylmethoxymethylhex-3-ene

Guidance literature:: Multi-step reaction with 8 steps

1.1: 86 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

2.1: hydrogen / Pd-C / ethanol / 2 h / 20 °C

3.1: 8.82 g / LiOH*H₂O / H₂O; methanol; tetrahydrofuran / 2 h / 20 °C

4.1: PivCl; Et₃N / tetrahydrofuran / 0.75 h / 0 °C

4.2: 88 percent / LiCl / tetrahydrofuran / 2 h / 20 °C

5.1: LHMDS / tetrahydrofuran / 0.75 h / -78 °C

5.2: 78 percent / LiI / tetrahydrofuran / 1 h / -50 °C

6.1: 91 percent / LiBH₄ / ethanol; tetrahydrofuran; H₂O / 2 h / 0 °C

7.1: tetra-n-propylammonium perruthenate; NMO; MS₄Angstroem / CH₂Cl₂

8.1: LMHDS / tetrahydrofuran / 1 h / -78 °C

8.2: 0.93 g / -78 °C

With 2,6-dimethylpyridine; lithium hydroxide; lithium borohydride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; MS₄Angstroem; hydrogen; pivaloyl chloride; triethylamine; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; 8.2: Julia olefination;
DOI:10.3987/com-03-9952