(3S,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-6-[(2S,4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-4,4-dimethyl-5-oxo-heptanal

Base Information

Chemical Name:(3S,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-6-[(2S,4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-4,4-dimethyl-5-oxo-heptanal
CAS No.:218443-81-3
Molecular Formula:C₂₇H₄₄O₆Si
Molecular Weight:492.728
Hs Code.:

Synonyms:(3S,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-6-[(2S,4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-4,4-dimethyl-5-oxo-heptanal

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Chemical Property of (3S,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-6-[(2S,4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-4,4-dimethyl-5-oxo-heptanal

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Technology Process of (3S,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-6-[(2S,4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-4,4-dimethyl-5-oxo-heptanal

There total 9 articles about (3S,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-6-[(2S,4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-4,4-dimethyl-5-oxo-heptanal 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: 99.0%

: 186417-93-6
(-)-(2R,5S)-5-{[tert-butyl(dimethyl)silyl]oxy}-2-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]-4,4-dimethyloct-7-en-3-one

: 218443-81-3
(3S,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-6-[(2S,4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-4,4-dimethyl-5-oxo-heptanal

Guidance literature:: With ozone; triphenylphosphine; In methanol; dichloromethane; -78 deg C to room temp.;
DOI:10.1016/S0040-4039(96)02156-9

Reference yield:

: 78186-80-8
3,3-dimethyl-4-oxohex-1-ene

: 218443-81-3
(3S,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-6-[(2S,4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-4,4-dimethyl-5-oxo-heptanal

Guidance literature:: Multi-step reaction with 6 steps

1: LDA / tetrahydrofuran / 0.25 h / -90 °C

2: 89 percent / dichlorodicyanobenzoquinone, 4 Angstroem molecular sieve / CH₂Cl₂ / 2 h / -20 deg C to room temp.

3: 93 percent / O₃; Me₂S / CH₂Cl₂; methanol / -78 deg C to room temp.

4: 2.) NaOOH / 1.) -78 deg C, Et₂O, 1 h

5: 99 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

6: 99 percent / O₃; Ph₃P / CH₂Cl₂; methanol / -78 deg C to room temp.

With 2,6-dimethylpyridine; sodium hydroperoxide; dimethylsulfide; 4 A molecular sieve; ozone; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1016/S0040-4039(96)02156-9

Reference yield:

: 89238-99-3
O-(4-methoxybenzyl)-trichloroacetimidate

: 218443-81-3
(3S,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-6-[(2S,4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-4,4-dimethyl-5-oxo-heptanal

Guidance literature:: Multi-step reaction with 9 steps

1: 94 percent

2: 92 percent / DIBAL-H

3: Swern oxidation

4: LDA / tetrahydrofuran / 0.25 h / -90 °C

5: 89 percent / dichlorodicyanobenzoquinone, 4 Angstroem molecular sieve / CH₂Cl₂ / 2 h / -20 deg C to room temp.

6: 93 percent / O₃; Me₂S / CH₂Cl₂; methanol / -78 deg C to room temp.

7: 2.) NaOOH / 1.) -78 deg C, Et₂O, 1 h

8: 99 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

9: 99 percent / O₃; Ph₃P / CH₂Cl₂; methanol / -78 deg C to room temp.

With 2,6-dimethylpyridine; sodium hydroperoxide; dimethylsulfide; 4 A molecular sieve; diisobutylaluminium hydride; ozone; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1016/S0040-4039(96)02156-9