methyl 6-(6-{(1E)(4S)-5-[(4-methoxyphenyl)methoxy]-2-methyl-4-(tert-butyldimethylsiloxy)pent-1-enyl}(4R,5R,6R)-2,2,5-trimethyl(1,3-dioxan-4-yl))(5S,6R)-5-hydroxy-3-oxoheptanoate

Base Information

Chemical Name:methyl 6-(6-{(1E)(4S)-5-[(4-methoxyphenyl)methoxy]-2-methyl-4-(tert-butyldimethylsiloxy)pent-1-enyl}(4R,5R,6R)-2,2,5-trimethyl(1,3-dioxan-4-yl))(5S,6R)-5-hydroxy-3-oxoheptanoate
CAS No.:439143-45-0
Molecular Formula:C₃₅H₅₈O₉Si
Molecular Weight:650.926
Hs Code.:

methyl 6-(6-{(1E)(4S)-5-[(4-methoxyphenyl)methoxy]-2-methyl-4-(tert-butyldimethylsiloxy)pent-1-enyl}(4R,5R,6R)-2,2,5-trimethyl(1,3-dioxan-4-yl))(5S,6R)-5-hydroxy-3-oxoheptanoate

Synonyms:methyl 6-(6-{(1E)(4S)-5-[(4-methoxyphenyl)methoxy]-2-methyl-4-(tert-butyldimethylsiloxy)pent-1-enyl}(4R,5R,6R)-2,2,5-trimethyl(1,3-dioxan-4-yl))(5S,6R)-5-hydroxy-3-oxoheptanoate

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Chemical Property of methyl 6-(6-{(1E)(4S)-5-[(4-methoxyphenyl)methoxy]-2-methyl-4-(tert-butyldimethylsiloxy)pent-1-enyl}(4R,5R,6R)-2,2,5-trimethyl(1,3-dioxan-4-yl))(5S,6R)-5-hydroxy-3-oxoheptanoate

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Technology Process of methyl 6-(6-{(1E)(4S)-5-[(4-methoxyphenyl)methoxy]-2-methyl-4-(tert-butyldimethylsiloxy)pent-1-enyl}(4R,5R,6R)-2,2,5-trimethyl(1,3-dioxan-4-yl))(5S,6R)-5-hydroxy-3-oxoheptanoate

There total 9 articles about methyl 6-(6-{(1E)(4S)-5-[(4-methoxyphenyl)methoxy]-2-methyl-4-(tert-butyldimethylsiloxy)pent-1-enyl}(4R,5R,6R)-2,2,5-trimethyl(1,3-dioxan-4-yl))(5S,6R)-5-hydroxy-3-oxoheptanoate 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: 88.0%

: 81114-98-9
Chan's diene

: 439143-44-9
2-(6-{(1E)(4S)-5-[(4-methoxyphenyl)methoxy]-2-methyl-4-(tert-butyldimethylsilyloxy)pent-1-enyl}(4S,5R,6R)-2,2,5-trimethyl(1,3-dioxan-4-yl))(2S)propanal

: 439143-45-0
methyl 6-(6-{(1E)(4S)-5-[(4-methoxyphenyl)methoxy]-2-methyl-4-(tert-butyldimethylsiloxy)pent-1-enyl}(4R,5R,6R)-2,2,5-trimethyl(1,3-dioxan-4-yl))(5S,6R)-5-hydroxy-3-oxoheptanoate

Guidance literature:: With boron trifluoride diethyl etherate; In toluene; at -85 ℃; for 0.75h;
DOI:10.1016/j.tet.2008.02.001

Reference yield:

: 81114-98-9
Chan's diene

: 439143-44-9
2-(6-{(1E)(4S)-5-[(4-methoxyphenyl)methoxy]-2-methyl-4-(tert-butyldimethylsilyloxy)pent-1-enyl}(4S,5R,6R)-2,2,5-trimethyl(1,3-dioxan-4-yl))(2S)propanal

: (5R,6R)-6-{(4R,5R,6R)-6-[(E)-(S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2-methyl-pent-1-enyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-5-hydroxy-3-oxo-heptanoic acid methyl ester

: 439143-45-0
methyl 6-(6-{(1E)(4S)-5-[(4-methoxyphenyl)methoxy]-2-methyl-4-(tert-butyldimethylsiloxy)pent-1-enyl}(4R,5R,6R)-2,2,5-trimethyl(1,3-dioxan-4-yl))(5S,6R)-5-hydroxy-3-oxoheptanoate

Guidance literature:: With boron trifluoride diethyl etherate; In toluene; at -90 ℃;
DOI:10.1021/ja026235n

Reference yield:

: 101712-01-0
(S)-1-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-2-methylpentane-1,3-dione

: 439143-45-0
methyl 6-(6-{(1E)(4S)-5-[(4-methoxyphenyl)methoxy]-2-methyl-4-(tert-butyldimethylsiloxy)pent-1-enyl}(4R,5R,6R)-2,2,5-trimethyl(1,3-dioxan-4-yl))(5S,6R)-5-hydroxy-3-oxoheptanoate

Guidance literature:: Multi-step reaction with 7 steps

1.1: Cy₂BCl; Et₃NMe₂ / diethyl ether / 0 °C

1.2: diethyl ether / -78 - -20 °C

2.1: Me₄NBH(OAc)3; AcOH / acetonitrile / 0 °C

3.1: HN(CH₂CH₂OH)2 / ethyl acetate / 20 °C

4.1: AlMe₃ / CH₂Cl₂ / 0 - 20 °C

5.1: PPTS / acetone / 20 °C

6.1: LiAlH₄ / diethyl ether / 20 °C

7.1: BF₃*OEt₂ / toluene / -90 °C

With lithium aluminium tetrahydride; boron trifluoride diethyl etherate; dicyclohexylboron chloride; trimethylaluminum; pyridinium p-toluenesulfonate; acetic acid; 2,2'-iminobis[ethanol]; tetramethylammonium triacetoxyborohydride; In diethyl ether; dichloromethane; ethyl acetate; acetone; toluene; acetonitrile;
DOI:10.1021/ja026235n