(Z)-(4R,5S,6S)-5-(tert-butyldimethylsilyloxy)-7-(tert-butyldiphenylsilyloxy)-6-methoxy-2,4-dimethyl-hept-2-enoic acid ethyl ester

Base Information

Chemical Name:(Z)-(4R,5S,6S)-5-(tert-butyldimethylsilyloxy)-7-(tert-butyldiphenylsilyloxy)-6-methoxy-2,4-dimethyl-hept-2-enoic acid ethyl ester
CAS No.:944823-24-9
Molecular Formula:C₃₄H₅₄O₅Si₂
Molecular Weight:598.971
Hs Code.:

Synonyms:(Z)-(4R,5S,6S)-5-(tert-butyldimethylsilyloxy)-7-(tert-butyldiphenylsilyloxy)-6-methoxy-2,4-dimethyl-hept-2-enoic acid ethyl ester

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Chemical Property of (Z)-(4R,5S,6S)-5-(tert-butyldimethylsilyloxy)-7-(tert-butyldiphenylsilyloxy)-6-methoxy-2,4-dimethyl-hept-2-enoic acid ethyl ester

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Technology Process of (Z)-(4R,5S,6S)-5-(tert-butyldimethylsilyloxy)-7-(tert-butyldiphenylsilyloxy)-6-methoxy-2,4-dimethyl-hept-2-enoic acid ethyl ester

There total 8 articles about (Z)-(4R,5S,6S)-5-(tert-butyldimethylsilyloxy)-7-(tert-butyldiphenylsilyloxy)-6-methoxy-2,4-dimethyl-hept-2-enoic acid ethyl ester 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:

: 848035-32-5
C₂₉H₄₆O₄Si₂

: 107905-52-2
ethyl 2-[bis(2,2,2-trifluoroethyl)phosphono]propionate

: (E)-(4R,5S,6S)-5-(tert-butyldimethylsilyloxy)-7-(tert-butyldiphenylsilyloxy)-6-methoxy-2,4-dimethyl-hept-2-enoic acid ethyl ester

: 944823-24-9
(Z)-(4R,5S,6S)-5-(tert-butyldimethylsilyloxy)-7-(tert-butyldiphenylsilyloxy)-6-methoxy-2,4-dimethyl-hept-2-enoic acid ethyl ester

Guidance literature:: ethyl 2-[bis(2,2,2-trifluoroethyl)phosphono]propionate; With 18-crown-6 ether; potassium hexamethylsilazane; In tetrahydrofuran; toluene; at 0 ℃; for 0.5h;

C₂₉H₄₆O₄Si₂; In tetrahydrofuran; toluene; at -78 ℃; for 18h; Further stages.;
DOI:10.1016/j.tet.2007.02.107

Reference yield:

: 918868-38-9
(2S)-methyl 3-(tert-butyldiphenylsilyloxy)-2-methoxy-propionate

: 944823-24-9
(Z)-(4R,5S,6S)-5-(tert-butyldimethylsilyloxy)-7-(tert-butyldiphenylsilyloxy)-6-methoxy-2,4-dimethyl-hept-2-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 90 percent / DIBAL-H / CH₂Cl₂; hexane / 2.5 h / 20 °C

2.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

3.1: MgBr₂*OEt₂ / CH₂Cl₂ / 0.67 h / -21 °C

3.2: 87 percent / CH₂Cl₂ / 7 h / -60 °C

4.1: 93 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / 0 °C

5.1: OsO₄; N-methylmorpholine N-oxide / 2-methyl-propan-2-ol; H₂O / 6.5 h / 20 °C

6.1: NaIO₄ / tetrahydrofuran; H₂O / 3 h / 20 °C

7.1: 18-crown-6; KHMDS / tetrahydrofuran; toluene / 0.5 h / 0 °C

7.2: 4.77 g / tetrahydrofuran; toluene / 18 h / -78 °C

With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; oxalyl dichloride; 18-crown-6 ether; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; magnesium bromide; In tetrahydrofuran; hexane; dichloromethane; water; toluene; tert-butyl alcohol; 2.1: Swern oxidation / 7.2: Still-Gennari olefination;
DOI:10.1016/j.tet.2007.02.107

Reference yield:

: 848035-35-8
(2S,3S,4R)-1-(tert-butyldiphenylsilyloxy)-2-methoxy-4-methyl-hex-5-en-3-ol

: 944823-24-9
(Z)-(4R,5S,6S)-5-(tert-butyldimethylsilyloxy)-7-(tert-butyldiphenylsilyloxy)-6-methoxy-2,4-dimethyl-hept-2-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 93 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / 0 °C

2.1: OsO₄; N-methylmorpholine N-oxide / 2-methyl-propan-2-ol; H₂O / 6.5 h / 20 °C

3.1: NaIO₄ / tetrahydrofuran; H₂O / 3 h / 20 °C

4.1: 18-crown-6; KHMDS / tetrahydrofuran; toluene / 0.5 h / 0 °C

4.2: 4.77 g / tetrahydrofuran; toluene / 18 h / -78 °C

With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; 18-crown-6 ether; potassium hexamethylsilazane; 4-methylmorpholine N-oxide; In tetrahydrofuran; dichloromethane; water; toluene; tert-butyl alcohol; 4.2: Still-Gennari olefination;
DOI:10.1016/j.tet.2007.02.107