(4S,5S,6S)-6-[(tert-butyldimethylsilyl)oxy]-4-methoxy-8-[(4-methoxybenzyl)oxy]-3,3,5-trimethyloctan-2-one

Base Information

Chemical Name:(4S,5S,6S)-6-[(tert-butyldimethylsilyl)oxy]-4-methoxy-8-[(4-methoxybenzyl)oxy]-3,3,5-trimethyloctan-2-one
CAS No.:1268687-85-9
Molecular Formula:C₂₆H₄₆O₅Si
Molecular Weight:466.734
Hs Code.:

Synonyms:(4S,5S,6S)-6-[(tert-butyldimethylsilyl)oxy]-4-methoxy-8-[(4-methoxybenzyl)oxy]-3,3,5-trimethyloctan-2-one

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Chemical Property of (4S,5S,6S)-6-[(tert-butyldimethylsilyl)oxy]-4-methoxy-8-[(4-methoxybenzyl)oxy]-3,3,5-trimethyloctan-2-one

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Technology Process of (4S,5S,6S)-6-[(tert-butyldimethylsilyl)oxy]-4-methoxy-8-[(4-methoxybenzyl)oxy]-3,3,5-trimethyloctan-2-one

There total 8 articles about (4S,5S,6S)-6-[(tert-butyldimethylsilyl)oxy]-4-methoxy-8-[(4-methoxybenzyl)oxy]-3,3,5-trimethyloctan-2-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: 98.0%

: 1268687-84-8
methyl (3S,4S,5S)-5-[(tert-butyldimethylsilyl)oxy]-3-methoxy-7-[(4-methoxybenzyl)oxy]-2,2,4-trimethylheptanoate

: 1822-00-0
trimethylsilylmethyllithium

: 1268687-85-9
(4S,5S,6S)-6-[(tert-butyldimethylsilyl)oxy]-4-methoxy-8-[(4-methoxybenzyl)oxy]-3,3,5-trimethyloctan-2-one

Guidance literature:: In pentane; at 0 ℃; for 3h;
DOI:10.1002/anie.201005605

Reference yield:

: 1268687-99-5
methyl (3S,4S,5S)-5-[(tert-butyldimethylsilyl)oxy]-3-hydroxy-7-[(4-methoxybenzyl)oxy]-2,2,4-trimethylheptanoate

: 1268687-85-9
(4S,5S,6S)-6-[(tert-butyldimethylsilyl)oxy]-4-methoxy-8-[(4-methoxybenzyl)oxy]-3,3,5-trimethyloctan-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: proton sponge / dichloromethane / 48 h / -20 °C

2: pentane / 3 h / 0 °C

With proton sponge; In dichloromethane; pentane;
DOI:10.1002/anie.201005605

Reference yield:

: 1268687-98-4
(2S,3S)-3-[(tert-butyldimethylsilyl)oxy]-5-[(4-methoxybenzyl)oxy]-2-methylpentan-1-ol

: 1268687-85-9
(4S,5S,6S)-6-[(tert-butyldimethylsilyl)oxy]-4-methoxy-8-[(4-methoxybenzyl)oxy]-3,3,5-trimethyloctan-2-one

Guidance literature:: Multi-step reaction with 4 steps

1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0 - 20 °C

2: calcium hydride; boron trifluoride diethyl etherate / dichloromethane / 3 h / -78 °C

3: proton sponge / dichloromethane / 48 h / -20 °C

4: pentane / 3 h / 0 °C

With calcium hydride; boron trifluoride diethyl etherate; sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; pentane; 1: Dess-Martin oxidation / 2: Mukaiyama reaction;
DOI:10.1002/anie.201005605