2-Butenoic acid, 4-[(2R,5R,6S)-6-ethoxy-5,6-dihydro-5-(3-methyl-2-butenyl)-2H-pyran-2- yl]-3-methyl-4-[[tris(1-methylethyl)silyl]oxy]-, ethyl ester, (2E,4R)-

Base Information

Chemical Name:2-Butenoic acid, 4-[(2R,5R,6S)-6-ethoxy-5,6-dihydro-5-(3-methyl-2-butenyl)-2H-pyran-2- yl]-3-methyl-4-[[tris(1-methylethyl)silyl]oxy]-, ethyl ester, (2E,4R)-
CAS No.:848188-01-2
Molecular Formula:C28H50O5Si
Molecular Weight:494.788
Hs Code.:

2-Butenoic acid,
4-[(2R,5R,6S)-6-ethoxy-5,6-dihydro-5-(3-methyl-2-butenyl)-2H-pyran-2-
yl]-3-methyl-4-[[tris(1-methylethyl)silyl]oxy]-, ethyl ester, (2E,4R)-

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Chemical Property of 2-Butenoic acid, 4-[(2R,5R,6S)-6-ethoxy-5,6-dihydro-5-(3-methyl-2-butenyl)-2H-pyran-2- yl]-3-methyl-4-[[tris(1-methylethyl)silyl]oxy]-, ethyl ester, (2E,4R)-

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Technology Process of 2-Butenoic acid, 4-[(2R,5R,6S)-6-ethoxy-5,6-dihydro-5-(3-methyl-2-butenyl)-2H-pyran-2- yl]-3-methyl-4-[[tris(1-methylethyl)silyl]oxy]-, ethyl ester, (2E,4R)-

There total 1 articles about 2-Butenoic acid, 4-[(2R,5R,6S)-6-ethoxy-5,6-dihydro-5-(3-methyl-2-butenyl)-2H-pyran-2- yl]-3-methyl-4-[[tris(1-methylethyl)silyl]oxy]-, ethyl ester, (2E,4R)- 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: 93.0%

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 848188-00-1
(E)-(R)-4-[(2R,5R,6S)-6-Ethoxy-5-(3-methyl-but-2-enyl)-5,6-dihydro-2H-pyran-2-yl]-4-hydroxy-3-methyl-but-2-enoic acid ethyl ester

: 848188-01-2
(E)-(R)-4-[(2R,5R,6S)-6-Ethoxy-5-(3-methyl-but-2-enyl)-5,6-dihydro-2H-pyran-2-yl]-3-methyl-4-triisopropylsilanyloxy-but-2-enoic acid ethyl ester

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 - 20 ℃;
DOI:10.1021/ja042827p

Reference yield:

: 848188-01-2
(E)-(R)-4-[(2R,5R,6S)-6-Ethoxy-5-(3-methyl-but-2-enyl)-5,6-dihydro-2H-pyran-2-yl]-3-methyl-4-triisopropylsilanyloxy-but-2-enoic acid ethyl ester

: {(2R,3S,3aR,6S,7R,7aS)-2-Methyl-6-[2-(1-phenyl-1H-tetrazole-5-sulfonyl)-ethyl]-3,7-bis-triisopropylsilanyloxy-hexahydro-furo[3,2-b]pyran-2-yl}-acetic acid ethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: OsO₄; potassium ferricyanide; (DHDQ)2PHAL / K₂CO₃; methanesulfonamide / 2-methyl-propan-2-ol; H₂O / 2 h / 0 °C

1.2: NaIO₄ / tetrahydrofuran; H₂O / 1 h / 20 °C

2.1: 8.98 g / NaBH₄ / ethanol / 0.5 h

3.1: 85 percent / TiCl₄; Et₃SiH / CH₂Cl₂ / 2.5 h / -50 °C

4.1: PPh₃; DIAD / tetrahydrofuran / 4 h / 20 °C

5.1: 7.65 g / aq. H₂O₂; ammonium molybdate tetrahydrate / ethanol / 20 °C

6.1: 87 percent / OsO₄; N-methylmorpholine N-oxide monohydrate / acetone; H₂O; 2-methyl-propan-2-ol / 20 °C

7.1: 88 percent / 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

With 2,6-dimethylpyridine; triethylsilane; sodium tetrahydroborate; osmium(VIII) oxide; ammonium molybdate(VI) tetrahydrate; di-isopropyl azodicarboxylate; dihydrogen peroxide; titanium tetrachloride; 4-methylmorpholine N-oxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; triphenylphosphine; potassium hexacyanoferrate(III); methanesulfonamide; potassium carbonate; In tetrahydrofuran; ethanol; dichloromethane; water; acetone; tert-butyl alcohol;
DOI:10.1021/ja042827p

Reference yield:

: 848188-01-2
(E)-(R)-4-[(2R,5R,6S)-6-Ethoxy-5-(3-methyl-but-2-enyl)-5,6-dihydro-2H-pyran-2-yl]-3-methyl-4-triisopropylsilanyloxy-but-2-enoic acid ethyl ester

: (E)-(R)-3-Methyl-4-{(2R,5R)-5-[2-(1-phenyl-1H-tetrazol-5-ylsulfanyl)-ethyl]-5,6-dihydro-2H-pyran-2-yl}-4-triisopropylsilanyloxy-but-2-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: OsO₄; potassium ferricyanide; (DHDQ)2PHAL / K₂CO₃; methanesulfonamide / 2-methyl-propan-2-ol; H₂O / 2 h / 0 °C

1.2: NaIO₄ / tetrahydrofuran; H₂O / 1 h / 20 °C

2.1: 8.98 g / NaBH₄ / ethanol / 0.5 h

3.1: 85 percent / TiCl₄; Et₃SiH / CH₂Cl₂ / 2.5 h / -50 °C

4.1: PPh₃; DIAD / tetrahydrofuran / 4 h / 20 °C

With triethylsilane; sodium tetrahydroborate; osmium(VIII) oxide; di-isopropyl azodicarboxylate; titanium tetrachloride; 1,4-bis(9-O-dihydroquinidine)phthalazine; triphenylphosphine; potassium hexacyanoferrate(III); methanesulfonamide; potassium carbonate; In tetrahydrofuran; ethanol; dichloromethane; water; tert-butyl alcohol;
DOI:10.1021/ja042827p