(E)-(S)-5-{(4R,5R)-5-[(1E,3E)-7-(tert-Butyl-diphenyl-silanyloxy)-hepta-1,3-dienyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4-oxo-hex-2-enoic acid methyl ester

Base Information

Chemical Name:(E)-(S)-5-{(4R,5R)-5-[(1E,3E)-7-(tert-Butyl-diphenyl-silanyloxy)-hepta-1,3-dienyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4-oxo-hex-2-enoic acid methyl ester
CAS No.:111649-66-2
Molecular Formula:C₃₅H₄₆O₆Si
Molecular Weight:590.832
Hs Code.:

(E)-(S)-5-{(4R,5R)-5-[(1E,3E)-7-(tert-Butyl-diphenyl-silanyloxy)-hepta-1,3-dienyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4-oxo-hex-2-enoic acid methyl ester

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Chemical Property of (E)-(S)-5-{(4R,5R)-5-[(1E,3E)-7-(tert-Butyl-diphenyl-silanyloxy)-hepta-1,3-dienyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4-oxo-hex-2-enoic acid methyl ester

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Technology Process of (E)-(S)-5-{(4R,5R)-5-[(1E,3E)-7-(tert-Butyl-diphenyl-silanyloxy)-hepta-1,3-dienyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4-oxo-hex-2-enoic acid methyl ester

There total 34 articles about (E)-(S)-5-{(4R,5R)-5-[(1E,3E)-7-(tert-Butyl-diphenyl-silanyloxy)-hepta-1,3-dienyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4-oxo-hex-2-enoic acid methyl 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: 57.0%

: 922-68-9
Methyl glyoxylate

: 118419-02-6,118419-05-9,118490-73-6,118490-74-7
((R)-3-{(4S,5R)-5-[(1Z,3Z)-7-(tert-Butyl-diphenyl-silanyloxy)-hepta-1,3-dienyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-oxo-butyl)-phosphonic acid dimethyl ester

: 111649-66-2,118490-67-8,118490-68-9,118490-69-0,120053-55-6
(E)-(R)-5-{(4S,5R)-5-[(1Z,3Z)-7-(tert-Butyl-diphenyl-silanyloxy)-hepta-1,3-dienyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4-oxo-hex-2-enoic acid methyl ester

Guidance literature:: With N-ethyl-N,N-diisopropylamine; lithium chloride; In acetonitrile; for 0.0833333h;
DOI:10.1021/jo00265a036

Reference yield:

: 88424-95-7
2,3-O-isopropylidene-1-C-<(1S)-1-methylprop-2-enyl>-D-erythro-glycerol

: 111649-66-2,118490-67-8,118490-68-9,118490-69-0,120053-55-6
(E)-(R)-5-{(4S,5R)-5-[(1Z,3Z)-7-(tert-Butyl-diphenyl-silanyloxy)-hepta-1,3-dienyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4-oxo-hex-2-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: AcOH / H₂O

2: Et₃N, DMAP / CH₂Cl₂

3: p-TsOH

4: 1.) ozone, 2.) Me₂S / 1.) methanol, -78 deg C, 2.) 2 h

5: MCPBA / CH₂Cl₂ / 1 h

6: CH₂Cl₂; diethyl ether

7: 88 percent / Et₃NHF / acetonitrile

8: DMSO, (COCl)2 / CH₂Cl₂ / 0.17 h / -78 °C

10: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 40 min, 2.) 10 min

11: 57 percent / LiCl, diisopropylethylamine / acetonitrile / 0.08 h

With dmap; n-butyllithium; oxalyl dichloride; dimethylsulfide; toluene-4-sulfonic acid; ozone; acetic acid; dimethyl sulfoxide; triethylamine hydrofluoride; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; lithium chloride; In diethyl ether; dichloromethane; water; acetonitrile;
DOI:10.1021/jo00265a036

Reference yield:

: 88424-94-6
(1R,2R)-2-methyl-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol

: 111649-66-2
(E)-(S)-5-{(4R,5R)-5-[(1E,3E)-7-(tert-Butyl-diphenyl-silanyloxy)-hepta-1,3-dienyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4-oxo-hex-2-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 94 percent / p-TsOH / acetone / 48 h / 23 °C

2: 1.) ozone, 2.) Me₂S / 1.) methanol, -78 deg C, 2.) 2 h

3: MCPBA / CH₂Cl₂ / 1 h

4: CH₂Cl₂; diethyl ether

5: 1.) DMSO, (COCl)2 / CH₂Cl₂ / 0.17 h / -78 °C

7: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 40 min, 2.) 10 min

8: LiCl, diisopropylethylamine / acetonitrile / 0.08 h

With n-butyllithium; oxalyl dichloride; dimethylsulfide; toluene-4-sulfonic acid; ozone; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; lithium chloride; In diethyl ether; dichloromethane; acetone; acetonitrile;
DOI:10.1021/jo00265a036