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

Base Information

Chemical Name:methyl (3S,4S,5S)-5-[(tert-butyldimethylsilyl)oxy]-3-hydroxy-7-[(4-methoxybenzyl)oxy]-2,2,4-trimethylheptanoate
CAS No.:1268687-99-5
Molecular Formula:C₂₅H₄₄O₆Si
Molecular Weight:468.706
Hs Code.:

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

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Chemical Property of methyl (3S,4S,5S)-5-[(tert-butyldimethylsilyl)oxy]-3-hydroxy-7-[(4-methoxybenzyl)oxy]-2,2,4-trimethylheptanoate

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Technology Process of methyl (3S,4S,5S)-5-[(tert-butyldimethylsilyl)oxy]-3-hydroxy-7-[(4-methoxybenzyl)oxy]-2,2,4-trimethylheptanoate

There total 6 articles about methyl (3S,4S,5S)-5-[(tert-butyldimethylsilyl)oxy]-3-hydroxy-7-[(4-methoxybenzyl)oxy]-2,2,4-trimethylheptanoate 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: 95.0%

: 31469-15-5
1-methoxy-2-methyl-1-trimethylsiloxy-1-propene

: (2R,3S)-3-[(tert-butyldimethylsilyl)oxy]-5-[(4-methoxybenzyl)oxy]-2-methylpentanal

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

Guidance literature:: With calcium hydride; boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 3h; optical yield given as %de; diastereoselective reaction;
DOI:10.1002/anie.201005605

Reference yield:

: 1194630-67-5
(R)-4-benzyl-3-{(2R,3S)-3-hydroxy-5-[(4-methoxybenzyl)oxy]-2-methyl-pentanoyl}oxazolidin-2-one

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

Guidance literature:: Multi-step reaction with 4 steps

1: 2,6-dimethylpyridine / dichloromethane / 3 h / -20 - 20 °C

2: lithium borohydride / tetrahydrofuran; methanol; diethyl ether / -10 - 0 °C

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

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

With 2,6-dimethylpyridine; lithium borohydride; calcium hydride; boron trifluoride diethyl etherate; sodium hydrogencarbonate; Dess-Martin periodane; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 3: Dess-Martin oxidation / 4: Mukaiyama reaction;
DOI:10.1002/anie.201005605

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 2 steps

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

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

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