(5S,6R,7R)-5-Hydroxy-7-(4-methoxy-benzyloxy)-2,2,6,8-tetramethyl-nonan-3-one

Base Information

Chemical Name:(5S,6R,7R)-5-Hydroxy-7-(4-methoxy-benzyloxy)-2,2,6,8-tetramethyl-nonan-3-one
CAS No.:380497-85-8
Molecular Formula:C₂₁H₃₄O₄
Molecular Weight:350.499
Hs Code.:

Synonyms:(5S,6R,7R)-5-Hydroxy-7-(4-methoxy-benzyloxy)-2,2,6,8-tetramethyl-nonan-3-one

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Chemical Property of (5S,6R,7R)-5-Hydroxy-7-(4-methoxy-benzyloxy)-2,2,6,8-tetramethyl-nonan-3-one

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Technology Process of (5S,6R,7R)-5-Hydroxy-7-(4-methoxy-benzyloxy)-2,2,6,8-tetramethyl-nonan-3-one

There total 7 articles about (5S,6R,7R)-5-Hydroxy-7-(4-methoxy-benzyloxy)-2,2,6,8-tetramethyl-nonan-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: 89.0%

: 17510-46-2
3,3-dimethyl-2-(trimethylsilyl)oxy-1-butene

: 162255-37-0
(2S,3R)-2,4-dimethyl-3-<(4-methoxybenzyl)oxy>pentanal

: 380497-85-8
(5S,6R,7R)-5-Hydroxy-7-(4-methoxy-benzyloxy)-2,2,6,8-tetramethyl-nonan-3-one

: 380497-83-6
(5R,6R,7R)-5-Hydroxy-7-(4-methoxy-benzyloxy)-2,2,6,8-tetramethyl-nonan-3-one

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 0.25h; Yields of byproduct given;
DOI:10.1021/ja953901u

Reference yield:

: 2186-92-7
p-Anisaldehyde dimethyl acetal

: 380497-85-8
(5S,6R,7R)-5-Hydroxy-7-(4-methoxy-benzyloxy)-2,2,6,8-tetramethyl-nonan-3-one

Guidance literature:: Multi-step reaction with 4 steps

1: TsOH / CH₂Cl₂ / 3 h / Ambient temperature

2: 98 percent / DIBAL-H / CH₂Cl₂; toluene / 0.75 h / 0 °C

3: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 10 min, 2.) CH₂Cl₂, -78 deg C, 45 min

4: 1.) LDA / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, -78 deg C, 2 min

With oxalyl dichloride; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In dichloromethane; toluene;
DOI:10.1021/ja953901u

Reference yield:

: 131832-48-9
(4S)-4-benzyl-3-[(2S,3R)-3-hydroxy-2,4-dimethylpentanoyl]oxazolidin-2-one

: 380497-85-8
(5S,6R,7R)-5-Hydroxy-7-(4-methoxy-benzyloxy)-2,2,6,8-tetramethyl-nonan-3-one

Guidance literature:: Multi-step reaction with 5 steps

1: LiBH₄ / methanol; tetrahydrofuran / 45 h / 0 °C

2: TsOH / CH₂Cl₂ / 3 h / Ambient temperature

3: 98 percent / DIBAL-H / CH₂Cl₂; toluene / 0.75 h / 0 °C

4: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 10 min, 2.) CH₂Cl₂, -78 deg C, 45 min

5: 1.) LDA / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, -78 deg C, 2 min

With lithium borohydride; oxalyl dichloride; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; toluene;
DOI:10.1021/ja953901u