(E)-(4S,6R)-7-Benzyloxy-6-hydroxy-1-[(2S,3R,6S)-3-hydroxy-6-(4-methoxy-benzyloxymethyl)-2-methyl-tetrahydro-pyran-2-yl]-4-methyl-hept-1-en-3-one

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Chemical Name:(E)-(4S,6R)-7-Benzyloxy-6-hydroxy-1-[(2S,3R,6S)-3-hydroxy-6-(4-methoxy-benzyloxymethyl)-2-methyl-tetrahydro-pyran-2-yl]-4-methyl-hept-1-en-3-one
CAS No.:388082-10-8
Molecular Formula:C₃₀H₄₀O₇
Molecular Weight:512.643
Hs Code.:

Synonyms:(E)-(4S,6R)-7-Benzyloxy-6-hydroxy-1-[(2S,3R,6S)-3-hydroxy-6-(4-methoxy-benzyloxymethyl)-2-methyl-tetrahydro-pyran-2-yl]-4-methyl-hept-1-en-3-one

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Chemical Property of (E)-(4S,6R)-7-Benzyloxy-6-hydroxy-1-[(2S,3R,6S)-3-hydroxy-6-(4-methoxy-benzyloxymethyl)-2-methyl-tetrahydro-pyran-2-yl]-4-methyl-hept-1-en-3-one

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Technology Process of (E)-(4S,6R)-7-Benzyloxy-6-hydroxy-1-[(2S,3R,6S)-3-hydroxy-6-(4-methoxy-benzyloxymethyl)-2-methyl-tetrahydro-pyran-2-yl]-4-methyl-hept-1-en-3-one

There total 17 articles about (E)-(4S,6R)-7-Benzyloxy-6-hydroxy-1-[(2S,3R,6S)-3-hydroxy-6-(4-methoxy-benzyloxymethyl)-2-methyl-tetrahydro-pyran-2-yl]-4-methyl-hept-1-en-3-one 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: 76.9%

: 388082-05-1
(E)-(2R,4S)-1-Benzyloxy-7-[(2S,3R,6S)-3-hydroxy-6-(4-methoxy-benzyloxymethyl)-2-methyl-tetrahydro-pyran-2-yl]-4-methyl-hept-6-ene-2,5-diol

: 388082-10-8
(E)-(4S,6R)-7-Benzyloxy-6-hydroxy-1-[(2S,3R,6S)-3-hydroxy-6-(4-methoxy-benzyloxymethyl)-2-methyl-tetrahydro-pyran-2-yl]-4-methyl-hept-1-en-3-one

Guidance literature:: With manganese(IV) oxide; In tetrahydrofuran; for 4h;
DOI:10.1021/ol016948v

Reference yield:

: 80910-01-6,108836-41-5,134733-19-0,144069-33-0
(S)-2-[(4-methoxybenzyloxy)methyl]oxirane

: 388082-10-8
(E)-(4S,6R)-7-Benzyloxy-6-hydroxy-1-[(2S,3R,6S)-3-hydroxy-6-(4-methoxy-benzyloxymethyl)-2-methyl-tetrahydro-pyran-2-yl]-4-methyl-hept-1-en-3-one

Guidance literature:: Multi-step reaction with 13 steps

1: CuI

2: imidazole

3: OsO₄; NMO

4: NaIO₄

5: DIBAL / -78 °C

6: 90 percent / Ti(O-i-Pr)4; (-)-DET; TBHP / -40 °C

7: 91 percent / Swern reagent

8: 92 percent / potassium hexamethyldisilazide / tetrahydrofuran; toluene / 2 h / -20 °C

9: 87 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 0.08 h / 0 °C

10: tetrabutylammonium fluoride / tetrahydrofuran / 12 h

11: 0.81 g / SiO₂

12: 76.9 percent / manganese(IV) oxide / tetrahydrofuran / 4 h

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; manganese(IV) oxide; sodium tetrahydroborate; sodium periodate; copper(l) iodide; osmium(VIII) oxide; N-methyl-2-indolinone; cerium(III) chloride; swern reagent; tetrabutyl ammonium fluoride; silica gel; potassium hexamethylsilazane; diisobutylaluminium hydride; (-)-diethyl tartrate; In tetrahydrofuran; methanol; toluene; 7: Sharpless asymmetric epoxidation / 8: Swern oxidation / 9: Horner-Wadsworth-Emmons olefination / 10: Luche reduction;
DOI:10.1021/ol016948v

Reference yield:

: 14618-80-5
(R)-benzyl glycidol

: 388082-10-8
(E)-(4S,6R)-7-Benzyloxy-6-hydroxy-1-[(2S,3R,6S)-3-hydroxy-6-(4-methoxy-benzyloxymethyl)-2-methyl-tetrahydro-pyran-2-yl]-4-methyl-hept-1-en-3-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: LDA; LiCl / -78 °C

1.2: 79 percent / H₂SO₄ / dioxane / 95 °C

2.1: BuLi / -78 °C

2.2: LDA / -78 °C

3.1: -78 - 20 °C

4.1: 92 percent / potassium hexamethyldisilazide / tetrahydrofuran; toluene / 2 h / -20 °C

5.1: 87 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 0.08 h / 0 °C

6.1: tetrabutylammonium fluoride / tetrahydrofuran / 12 h

7.1: 0.81 g / SiO₂

8.1: 76.9 percent / manganese(IV) oxide / tetrahydrofuran / 4 h

With manganese(IV) oxide; sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; tetrabutyl ammonium fluoride; silica gel; potassium hexamethylsilazane; lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; methanol; toluene; 4.1: Horner-Wadsworth-Emmons olefination / 5.1: Luche reduction;
DOI:10.1021/ol016948v