(2S,4S,5R,6R)-7-tert-butyldiphenylsilyloxy-5-hydroxy-2-(p-methoxybenzyloxy)-4,6-dimethyl-3-heptanone

Base Information

Chemical Name:(2S,4S,5R,6R)-7-tert-butyldiphenylsilyloxy-5-hydroxy-2-(p-methoxybenzyloxy)-4,6-dimethyl-3-heptanone
CAS No.:639006-75-0
Molecular Formula:C₃₃H₄₄O₅Si
Molecular Weight:548.795
Hs Code.:

Synonyms:(2S,4S,5R,6R)-7-tert-butyldiphenylsilyloxy-5-hydroxy-2-(p-methoxybenzyloxy)-4,6-dimethyl-3-heptanone

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2S,4S,5R,6R)-7-tert-butyldiphenylsilyloxy-5-hydroxy-2-(p-methoxybenzyloxy)-4,6-dimethyl-3-heptanone

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Technology Process of (2S,4S,5R,6R)-7-tert-butyldiphenylsilyloxy-5-hydroxy-2-(p-methoxybenzyloxy)-4,6-dimethyl-3-heptanone

There total 1 articles about (2S,4S,5R,6R)-7-tert-butyldiphenylsilyloxy-5-hydroxy-2-(p-methoxybenzyloxy)-4,6-dimethyl-3-heptanone 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: 82.0%

: 91751-24-5,92817-88-4,123284-89-9,112897-04-8
(R)-3-[(tert-butyldiphenylsilyl)oxy]-2-methylpropanal

: 312538-65-1
(S)-2-p-Methoxybenzyloxy-3-pentanone

: 639006-75-0
(2S,4S,5R,6R)-7-tert-butyldiphenylsilyloxy-5-hydroxy-2-(p-methoxybenzyloxy)-4,6-dimethyl-3-heptanone

Guidance literature:: (S)-2-p-Methoxybenzyloxy-3-pentanone; With titanium(IV) isopropylate; titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 ℃; for 1.5h;

(R)-3-[(tert-butyldiphenylsilyl)oxy]-2-methylpropanal; In dichloromethane; at -78 ℃; for 2h;
DOI:10.1021/ol035874f

Reference yield: 92.0%

: 639006-75-0
(2S,4S,5R,6R)-7-tert-butyldiphenylsilyloxy-5-hydroxy-2-(p-methoxybenzyloxy)-4,6-dimethyl-3-heptanone

: 639006-77-2
(2R,3R,4S,5S,6S)-1-tert-butyldiphenylsilyloxy-6-(4-methoxybenzyloxy)-2,4-dimethyl-3,5-heptanediol

: (2R,3R,4S,5R,6S)-1-tert-butyldiphenylsilyloxy-6-(4-methoxybenzyloxy)-2,4-dimethyl-3,5-heptanediol

Guidance literature:: With tetramethylammonium triacetoxyborohydride; In acetic acid; acetonitrile; at -40 - 0 ℃;
DOI:10.1021/ol035874f

Reference yield:

: 639006-75-0
(2S,4S,5R,6R)-7-tert-butyldiphenylsilyloxy-5-hydroxy-2-(p-methoxybenzyloxy)-4,6-dimethyl-3-heptanone

: (S)-1-{(4S,5S,6R)-6-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-ethanol

Guidance literature:: Multi-step reaction with 3 steps

1: 92 percent / (Me₄N)HB(OAc)3 / acetonitrile; acetic acid / -40 - 0 °C

2: 92 percent / PPTS / CH₂Cl₂ / 24 h / 20 °C

3: 396 mg / DDQ / CH₂Cl₂; aq. phosphate buffer / 2 h / 0 °C / pH 7

With pyridinium p-toluenesulfonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tetramethylammonium triacetoxyborohydride; In phosphate buffer; dichloromethane; acetic acid; acetonitrile;
DOI:10.1021/ol035874f