1-Hepten-3-ol, 6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-methoxy-4-methyl-1-phenyl-, (1E,3R,4R,5R)-

Base Information

Chemical Name:1-Hepten-3-ol, 6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-methoxy-4-methyl-1-phenyl-, (1E,3R,4R,5R)-
CAS No.:602277-07-6
Molecular Formula:C21H36O3Si
Molecular Weight:364.601
Hs Code.:

Synonyms:

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Chemical Property of 1-Hepten-3-ol, 6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-methoxy-4-methyl-1-phenyl-, (1E,3R,4R,5R)-

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Technology Process of 1-Hepten-3-ol, 6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-methoxy-4-methyl-1-phenyl-, (1E,3R,4R,5R)-

There total 11 articles about 1-Hepten-3-ol, 6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-methoxy-4-methyl-1-phenyl-, (1E,3R,4R,5R)- 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: 86.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 602277-06-5
(E)-(3R,4R,5R)-3-Methoxy-4-methyl-7-phenyl-hept-6-ene-2,5-diol

: 602277-07-6
(E)-(3R,4R,5R)-6-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-4-methyl-1-phenyl-hept-1-en-3-ol

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at -78 ℃; for 1.5h;
DOI:10.1016/S0040-4039(03)01256-5

Reference yield:

: 18546-21-9
1,2:5,6-di-O-cyclohexylidene-α-D-ribo-3-hexofuranose-3-ulose

: 602277-07-6
(E)-(3R,4R,5R)-6-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-4-methyl-1-phenyl-hept-1-en-3-ol

Guidance literature:: Multi-step reaction with 10 steps

1.1: 67 percent / tetrahydrofuran / 0.5 h / -10 °C

2.1: 97 percent / H₂ / Pd/C / 3 h / 2585.74 Torr

3.1: 83 percent / aq. H₂SO₄ / methanol / 24 h

4.1: MsCl; NEt₃ / CH₂Cl₂ / 2 h / 0 - 20 °C

4.2: EtCOMe; NaI / CH₂Cl₂ / 6 h / Heating

5.1: 63 percent / PPh₃; NEt₃; TBAI / Pd(OAc)2 / dimethylformamide / 6 h / 110 °C

6.1: 82 percent / Amberlyst IR-120 (H+) resin / methanol / 8 h / Heating

7.1: 95 percent / NaH / tetrahydrofuran / 3 h / 20 °C

8.1: 79 percent / H₂SO₄; aq. acetic acid / 6 h / 80 °C

9.1: 75 percent / tetrahydrofuran / 2.5 h / 20 °C

10.1: 86 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / -78 °C

With 2,6-dimethylpyridine; Amberlyst IR-120 (H+) resin; sulfuric acid; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; methanesulfonyl chloride; triethylamine; triphenylphosphine; palladium diacetate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1.1: Wittig reaction / 5.1: Heck reaction;
DOI:10.1016/S0040-4039(03)01256-5

Reference yield:

: 23397-76-4
1,2:5,6-di-O-cyclohexylidene-α-D-glucofuranose

: 602277-07-6
(E)-(3R,4R,5R)-6-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-4-methyl-1-phenyl-hept-1-en-3-ol

Guidance literature:: Multi-step reaction with 11 steps

1.1: 78 percent / PDC; 4 Angstroem MS; Ac₂O / CH₂Cl₂ / 12 h / 20 °C

2.1: 67 percent / tetrahydrofuran / 0.5 h / -10 °C

3.1: 97 percent / H₂ / Pd/C / 3 h / 2585.74 Torr

4.1: 83 percent / aq. H₂SO₄ / methanol / 24 h

5.1: MsCl; NEt₃ / CH₂Cl₂ / 2 h / 0 - 20 °C

5.2: EtCOMe; NaI / CH₂Cl₂ / 6 h / Heating

6.1: 63 percent / PPh₃; NEt₃; TBAI / Pd(OAc)2 / dimethylformamide / 6 h / 110 °C

7.1: 82 percent / Amberlyst IR-120 (H+) resin / methanol / 8 h / Heating

8.1: 95 percent / NaH / tetrahydrofuran / 3 h / 20 °C

9.1: 79 percent / H₂SO₄; aq. acetic acid / 6 h / 80 °C

10.1: 75 percent / tetrahydrofuran / 2.5 h / 20 °C

11.1: 86 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / -78 °C

With 2,6-dimethylpyridine; dipyridinium dichromate; 4 Angstroem MS; Amberlyst IR-120 (H+) resin; sulfuric acid; hydrogen; acetic anhydride; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; methanesulfonyl chloride; triethylamine; triphenylphosphine; palladium diacetate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 2.1: Wittig reaction / 6.1: Heck reaction;
DOI:10.1016/S0040-4039(03)01256-5