(7S,9S,2'R,4'S,6'R)-1-(6'-(2-benzyldimethylsilylethenyl)-2'-phenyl-[1,3]dioxan-4'yl)-7,9-dimetheyl-6-hydroxy-8-(4-methoxyphenylmethoxy)-5-nonen-2-one

Base Information

Chemical Name:(7S,9S,2'R,4'S,6'R)-1-(6'-(2-benzyldimethylsilylethenyl)-2'-phenyl-[1,3]dioxan-4'yl)-7,9-dimetheyl-6-hydroxy-8-(4-methoxyphenylmethoxy)-5-nonen-2-one
CAS No.:858676-66-1
Molecular Formula:C₄₁H₅₄O₆Si
Molecular Weight:670.962
Hs Code.:

Synonyms:(7S,9S,2'R,4'S,6'R)-1-(6'-(2-benzyldimethylsilylethenyl)-2'-phenyl-[1,3]dioxan-4'yl)-7,9-dimetheyl-6-hydroxy-8-(4-methoxyphenylmethoxy)-5-nonen-2-one

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Chemical Property of (7S,9S,2'R,4'S,6'R)-1-(6'-(2-benzyldimethylsilylethenyl)-2'-phenyl-[1,3]dioxan-4'yl)-7,9-dimetheyl-6-hydroxy-8-(4-methoxyphenylmethoxy)-5-nonen-2-one

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Technology Process of (7S,9S,2'R,4'S,6'R)-1-(6'-(2-benzyldimethylsilylethenyl)-2'-phenyl-[1,3]dioxan-4'yl)-7,9-dimetheyl-6-hydroxy-8-(4-methoxyphenylmethoxy)-5-nonen-2-one

There total 13 articles about (7S,9S,2'R,4'S,6'R)-1-(6'-(2-benzyldimethylsilylethenyl)-2'-phenyl-[1,3]dioxan-4'yl)-7,9-dimetheyl-6-hydroxy-8-(4-methoxyphenylmethoxy)-5-nonen-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: 85.0%

: 858676-55-8
(2'R,4'S,6'R)-3-(2'-phenyl-6'-(2-benzyldimethylsilylethenyl)-[1,3]dioxan-4'-yl)propan-2-one

: 323192-62-7
(4S,5S)-4,6-dimethyl-5-(p-methoxybenzyloxy)-trans-hept-2-enal

: (E)-(4S,7S,8S)-1-{(2R,4S,6R)-6-[(E)-2-(Benzyl-dimethyl-silanyl)-vinyl]-2-phenyl-[1,3]dioxan-4-yl}-4-hydroxy-8-(4-methoxy-benzyloxy)-7,9-dimethyl-dec-5-en-2-one

: 858676-66-1
(7S,9S,2'R,4'S,6'R)-1-(6'-(2-benzyldimethylsilylethenyl)-2'-phenyl-[1,3]dioxan-4'yl)-7,9-dimetheyl-6-hydroxy-8-(4-methoxyphenylmethoxy)-5-nonen-2-one

Guidance literature:: (2'R,4'S,6'R)-3-(2'-phenyl-6'-(2-benzyldimethylsilylethenyl)-[1,3]dioxan-4'-yl)propan-2-one; With di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; In diethyl ether; dichloromethane; at -72 ℃; for 0.25h;

(4S,5S)-4,6-dimethyl-5-(p-methoxybenzyloxy)-trans-hept-2-enal; In diethyl ether; dichloromethane; at -72 ℃; for 7h;
DOI:10.1021/ja052226d

Reference yield:

: 858676-59-2
(2E)-3-[benzyl(dimethyl)silyl]acrylaldehyde

: 858676-66-1
(7S,9S,2'R,4'S,6'R)-1-(6'-(2-benzyldimethylsilylethenyl)-2'-phenyl-[1,3]dioxan-4'yl)-7,9-dimetheyl-6-hydroxy-8-(4-methoxyphenylmethoxy)-5-nonen-2-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: 75 percent / SiCl₄; diisopropylethylamine; (R,R)-bisphosphoramide / CH₂Cl₂ / 3 h / -70 °C

2.1: 74 percent / KHMDS / tetrahydrofuran / 1 h / 0 °C

3.1: 87 percent / i-PrMgCl / tetrahydrofuran / -20 °C

4.1: 90 percent / MeMgBr / diethyl ether / 0 - 20 °C

5.1: 94 percent / DIPEA

6.1: SiCl₄; Hg(OAc)2

6.2: chiral cyclic phosphoramide derivative

With tetrachlorosilane; (R,R)-bisphosphoramide; methylmagnesium bromide; mercury(II) diacetate; isopropylmagnesium chloride; potassium hexamethylsilazane; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/ja052226d

Reference yield:

: 858676-57-0
(5R)-ethyl-7-benzyldimethylsilyl-5-hydroxy-hepta-2,6-dienoate

: 858676-66-1
(7S,9S,2'R,4'S,6'R)-1-(6'-(2-benzyldimethylsilylethenyl)-2'-phenyl-[1,3]dioxan-4'yl)-7,9-dimetheyl-6-hydroxy-8-(4-methoxyphenylmethoxy)-5-nonen-2-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: 74 percent / KHMDS / tetrahydrofuran / 1 h / 0 °C

2.1: 87 percent / i-PrMgCl / tetrahydrofuran / -20 °C

3.1: 90 percent / MeMgBr / diethyl ether / 0 - 20 °C

4.1: 94 percent / DIPEA

5.1: SiCl₄; Hg(OAc)2

5.2: chiral cyclic phosphoramide derivative

With tetrachlorosilane; methylmagnesium bromide; mercury(II) diacetate; isopropylmagnesium chloride; potassium hexamethylsilazane; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether;
DOI:10.1021/ja052226d