(7E,9E)-(1R,5R,12R,14R,15S,19S)-14-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-19-methoxy-5,12,17,17-tetramethyl-4,16,18-trioxa-bicyclo[13.3.1]nonadeca-7,9-diene-3,11-dione

Base Information

Chemical Name:(7E,9E)-(1R,5R,12R,14R,15S,19S)-14-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-19-methoxy-5,12,17,17-tetramethyl-4,16,18-trioxa-bicyclo[13.3.1]nonadeca-7,9-diene-3,11-dione
CAS No.:77234-54-9
Molecular Formula:C₃₉H₅₄O₇Si
Molecular Weight:662.939
Hs Code.:

(7E,9E)-(1R,5R,12R,14R,15S,19S)-14-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-19-methoxy-5,12,17,17-tetramethyl-4,16,18-trioxa-bicyclo[13.3.1]nonadeca-7,9-diene-3,11-dione

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Chemical Property of (7E,9E)-(1R,5R,12R,14R,15S,19S)-14-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-19-methoxy-5,12,17,17-tetramethyl-4,16,18-trioxa-bicyclo[13.3.1]nonadeca-7,9-diene-3,11-dione

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Technology Process of (7E,9E)-(1R,5R,12R,14R,15S,19S)-14-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-19-methoxy-5,12,17,17-tetramethyl-4,16,18-trioxa-bicyclo[13.3.1]nonadeca-7,9-diene-3,11-dione

There total 28 articles about (7E,9E)-(1R,5R,12R,14R,15S,19S)-14-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-19-methoxy-5,12,17,17-tetramethyl-4,16,18-trioxa-bicyclo[13.3.1]nonadeca-7,9-diene-3,11-dione 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: 95.0%

: 77405-60-8
(11E,13E)-(4R,5S,6S,7R,9R,16R)-7-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4,6-dihydroxy-5-methoxy-9,16-dimethyl-oxacyclohexadeca-11,13-diene-2,10-dione

: 77-76-9
2,2-dimethoxy-propane

: 77234-54-9,77286-12-5
(7E,9E)-(1R,5R,12R,14R,15S,19S)-14-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-19-methoxy-5,12,17,17-tetramethyl-4,16,18-trioxa-bicyclo[13.3.1]nonadeca-7,9-diene-3,11-dione

Guidance literature:: With camphor-10-sulfonic acid; In acetone; at 25 ℃;
DOI:10.1021/ja00395a043

Reference yield: 20.0%

: 77234-55-0,77286-45-4
{(4R,5S,6S)-6-[(1R,3R)-1-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-(dimethoxy-phosphoryl)-3-methyl-4-oxo-pentyl]-5-methoxy-2,2-dimethyl-[1,3]dioxan-4-yl}-acetic acid (E)-(R)-1-methyl-5-oxo-pent-3-enyl ester

: 77234-54-9,77286-12-5
(7E,9E)-(1R,5R,12R,14R,15S,19S)-14-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-19-methoxy-5,12,17,17-tetramethyl-4,16,18-trioxa-bicyclo[13.3.1]nonadeca-7,9-diene-3,11-dione

Guidance literature:: With sodium; In toluene; at 40 ℃;
DOI:10.1021/ja00395a044

Reference yield:

: 62853-46-7
5-deoxy-3-O-methyl-1,2-O-(methylethylidene)-α-D-xylo-hexo-furanose

: 77234-54-9,77286-12-5
(7E,9E)-(1R,5R,12R,14R,15S,19S)-14-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-19-methoxy-5,12,17,17-tetramethyl-4,16,18-trioxa-bicyclo[13.3.1]nonadeca-7,9-diene-3,11-dione

Guidance literature:: Multi-step reaction with 17 steps

1: 88 percent / NaH / 1,2-dimethoxy-ethane / 60 °C

2: 92 percent / amberlite 1R-120, H₂O / 100 °C

3: 80 percent / toluene / 25 °C

4: camphorsulfonic acid / benzene / 25 °C

5: 1.) cuprous iodide / 1) -40 deg C, THF; 2) -40 deg C, 4 h

6: 90 percent / aq. HCl / ethane-1,2-diol / 25 °C

7: 98 percent / LAH / diethyl ether / 0 °C

8: 80 percent / imidazole / dimethylformamide / 25 °C

9: 98 percent / camphorsulfonic acid / acetone

10: 1.) borane, 2.) NaOH-H₂O₂ / 1) THF, 0 deg C

11: 95 percent / PCC / CH₂Cl₂ / 0 °C

12: 1.) n-BuLi / 2.) THF, -78 deg C

13: PCC / CH₂Cl₂ / 25 °C

14: 100 percent / H₂ / Pd-C / ethyl acetate / 25 °C

15: 72 percent / Jones reagent / acetone / 0 °C

16: 70 percent / DCC, 4-(dimethylamino)pyridine / diethyl ether / 25 °C

17: 20 percent / Na / toluene / 40 °C

With 1H-imidazole; hydrogenchloride; dmap; sodium hydroxide; copper(l) iodide; lithium aluminium tetrahydride; n-butyllithium; jones reagent; amberlite 1R-120; camphor-10-sulfonic acid; borane; water; hydrogen; dihydrogen peroxide; sodium; sodium hydride; dicyclohexyl-carbodiimide; pyridinium chlorochromate; palladium on activated charcoal; In 1,2-dimethoxyethane; diethyl ether; dichloromethane; ethylene glycol; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; benzene;
DOI:10.1021/ja00395a044