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

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Chemical Name:(4S,6R)-7-Benzyloxy-6-hydroxy-1-[(2S,3R,6S)-3-hydroxy-6-(4-methoxy-benzyloxymethyl)-2-methyl-tetrahydro-pyran-2-yl]-4-methyl-heptan-3-one
CAS No.:388082-06-2
Molecular Formula:C₃₀H₄₂O₇
Molecular Weight:514.659
Hs Code.:

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

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

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

There total 18 articles about (4S,6R)-7-Benzyloxy-6-hydroxy-1-[(2S,3R,6S)-3-hydroxy-6-(4-methoxy-benzyloxymethyl)-2-methyl-tetrahydro-pyran-2-yl]-4-methyl-heptan-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:

: 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

: 388082-06-2
(4S,6R)-7-Benzyloxy-6-hydroxy-1-[(2S,3R,6S)-3-hydroxy-6-(4-methoxy-benzyloxymethyl)-2-methyl-tetrahydro-pyran-2-yl]-4-methyl-heptan-3-one

Guidance literature:: With tetrakis(triphenylphosphine) palladium⁽⁰⁾; ammonium chloride; tri-n-butyl-tin hydride; In tetrahydrofuran; water; for 1h;
DOI:10.1021/ol016948v

Reference yield:

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

: 388082-06-2
(4S,6R)-7-Benzyloxy-6-hydroxy-1-[(2S,3R,6S)-3-hydroxy-6-(4-methoxy-benzyloxymethyl)-2-methyl-tetrahydro-pyran-2-yl]-4-methyl-heptan-3-one

Guidance literature:: Multi-step reaction with 14 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

13: Bu₃SnH; palladium tetrakis(triphenylphosphine); ammonium chloride / tetrahydrofuran; H₂O / 1 h

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; manganese(IV) oxide; sodium tetrahydroborate; sodium periodate; copper(l) iodide; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; N-methyl-2-indolinone; cerium(III) chloride; swern reagent; ammonium chloride; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; silica gel; potassium hexamethylsilazane; diisobutylaluminium hydride; (-)-diethyl tartrate; In tetrahydrofuran; methanol; water; 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

: 388082-06-2
(4S,6R)-7-Benzyloxy-6-hydroxy-1-[(2S,3R,6S)-3-hydroxy-6-(4-methoxy-benzyloxymethyl)-2-methyl-tetrahydro-pyran-2-yl]-4-methyl-heptan-3-one

Guidance literature:: Multi-step reaction with 9 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

9.1: Bu₃SnH; palladium tetrakis(triphenylphosphine); ammonium chloride / tetrahydrofuran; H₂O / 1 h

With manganese(IV) oxide; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; cerium(III) chloride; ammonium chloride; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; silica gel; potassium hexamethylsilazane; lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; methanol; water; toluene; 4.1: Horner-Wadsworth-Emmons olefination / 5.1: Luche reduction;
DOI:10.1021/ol016948v