(4R,5R,6S,7R)-6-(benzyloxy)-5-<(benzyloxy)methoxy>-4,6-dimethyl-7-<(trimethylsilyl)oxy>nonan-3-one

Base Information

Chemical Name:(4R,5R,6S,7R)-6-(benzyloxy)-5-<(benzyloxy)methoxy>-4,6-dimethyl-7-<(trimethylsilyl)oxy>nonan-3-one
CAS No.:116103-31-2
Molecular Formula:C₂₉H₄₄O₅Si
Molecular Weight:500.751
Hs Code.:

Synonyms:(4R,5R,6S,7R)-6-(benzyloxy)-5-<(benzyloxy)methoxy>-4,6-dimethyl-7-<(trimethylsilyl)oxy>nonan-3-one

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Chemical Property of (4R,5R,6S,7R)-6-(benzyloxy)-5-<(benzyloxy)methoxy>-4,6-dimethyl-7-<(trimethylsilyl)oxy>nonan-3-one

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Technology Process of (4R,5R,6S,7R)-6-(benzyloxy)-5-<(benzyloxy)methoxy>-4,6-dimethyl-7-<(trimethylsilyl)oxy>nonan-3-one

There total 8 articles about (4R,5R,6S,7R)-6-(benzyloxy)-5-<(benzyloxy)methoxy>-4,6-dimethyl-7-<(trimethylsilyl)oxy>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: 94.0%

: 116103-42-5
(E,3R,4S,5R,6S)-4-(benzyloxy)-5-<(benzyloxy)methoxy>-7-ethyl-4,6-dimethyl-3-<(trimethylsilyl)oxy>non-7-ene

: 116103-31-2
(4R,5R,6S,7R)-6-(benzyloxy)-5-<(benzyloxy)methoxy>-4,6-dimethyl-7-<(trimethylsilyl)oxy>nonan-3-one

Guidance literature:: With O₃,K₂CO₃ buffer; In methanol; dichloromethane; at -70 ℃;
DOI:10.1021/jo00255a013

Reference yield:

: 92817-95-3
(E,2S)-3-ethyl-2-methylpent-3-enal

: 116103-31-2
(4R,5R,6S,7R)-6-(benzyloxy)-5-<(benzyloxy)methoxy>-4,6-dimethyl-7-<(trimethylsilyl)oxy>nonan-3-one

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) LDA / 1.) THF, -70 deg C, 30 min, 2.) 20 min

2: 97 percent / ethyl diisopropylamine / CH₂Cl₂ / 30 h / Heating

3: 72 percent / LiAlH₄ / diethyl ether / 9 h / Heating

4: 90 percent / oxalyl chloride, DMSO, / CH₂Cl₂ / 30 h / -70 °C

5: DMSO / 1.) 0 deg C, 30 min, 2.) THF, room temperature, 13 h

6: 48 percent / CuI, / tetrahydrofuran / 3 h / 0 °C

7: 81 percent / pyridine / CH₂Cl₂ / 1 h / -70 °C

8: 94 percent / O₃,K₂CO₃ buffer, / methanol; CH₂Cl₂ / -70 °C

With pyridine; copper(l) iodide; lithium aluminium tetrahydride; oxalyl dichloride; O₃,K₂CO₃ buffer; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;
DOI:10.1021/jo00255a013

Reference yield:

: 116103-37-8
(E,2R,3R,4S)-2-(benzyloxy)-3-<(benzyloxy)methoxy>-5-ethyl-2,4-dimethylhept-5-en-1-ol

: 116103-31-2
(4R,5R,6S,7R)-6-(benzyloxy)-5-<(benzyloxy)methoxy>-4,6-dimethyl-7-<(trimethylsilyl)oxy>nonan-3-one

Guidance literature:: Multi-step reaction with 5 steps

1: 90 percent / oxalyl chloride, DMSO, / CH₂Cl₂ / 30 h / -70 °C

2: DMSO / 1.) 0 deg C, 30 min, 2.) THF, room temperature, 13 h

3: 48 percent / CuI, / tetrahydrofuran / 3 h / 0 °C

4: 81 percent / pyridine / CH₂Cl₂ / 1 h / -70 °C

5: 94 percent / O₃,K₂CO₃ buffer, / methanol; CH₂Cl₂ / -70 °C

With pyridine; copper(l) iodide; oxalyl dichloride; O₃,K₂CO₃ buffer; dimethyl sulfoxide; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jo00255a013