(2R,3S,4S,5R,6S,9S,10S,11R,12R,13S)-6-(tert-butyldimethylsiloxy)-14-((tert-butyldiphenylsiloxy))-2,4-((R)-benzylidenedioxy)-10,12-(isopropylidenedioxy)-7-methylene-3,5,9,11,13-pentamethyltetradecane

Base Information

Chemical Name:(2R,3S,4S,5R,6S,9S,10S,11R,12R,13S)-6-(tert-butyldimethylsiloxy)-14-((tert-butyldiphenylsiloxy))-2,4-((R)-benzylidenedioxy)-10,12-(isopropylidenedioxy)-7-methylene-3,5,9,11,13-pentamethyltetradecane
CAS No.:251099-50-0
Molecular Formula:C₅₂H₈₀O₆Si₂
Molecular Weight:857.375
Hs Code.:

(2R,3S,4S,5R,6S,9S,10S,11R,12R,13S)-6-(tert-butyldimethylsiloxy)-14-((tert-butyldiphenylsiloxy))-2,4-((R)-benzylidenedioxy)-10,12-(isopropylidenedioxy)-7-methylene-3,5,9,11,13-pentamethyltetradecane

Synonyms:(2R,3S,4S,5R,6S,9S,10S,11R,12R,13S)-6-(tert-butyldimethylsiloxy)-14-((tert-butyldiphenylsiloxy))-2,4-((R)-benzylidenedioxy)-10,12-(isopropylidenedioxy)-7-methylene-3,5,9,11,13-pentamethyltetradecane

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Chemical Property of (2R,3S,4S,5R,6S,9S,10S,11R,12R,13S)-6-(tert-butyldimethylsiloxy)-14-((tert-butyldiphenylsiloxy))-2,4-((R)-benzylidenedioxy)-10,12-(isopropylidenedioxy)-7-methylene-3,5,9,11,13-pentamethyltetradecane

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Technology Process of (2R,3S,4S,5R,6S,9S,10S,11R,12R,13S)-6-(tert-butyldimethylsiloxy)-14-((tert-butyldiphenylsiloxy))-2,4-((R)-benzylidenedioxy)-10,12-(isopropylidenedioxy)-7-methylene-3,5,9,11,13-pentamethyltetradecane

There total 32 articles about (2R,3S,4S,5R,6S,9S,10S,11R,12R,13S)-6-(tert-butyldimethylsiloxy)-14-((tert-butyldiphenylsiloxy))-2,4-((R)-benzylidenedioxy)-10,12-(isopropylidenedioxy)-7-methylene-3,5,9,11,13-pentamethyltetradecane 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%

: 1779-49-3
Methyltriphenylphosphonium bromide

: 476622-77-2
(2R,3S,4S,5R,6S,9S,10S,11R,12R,13S)-6-(tert-butyldimethylsiloxy)-14-((tert-butyldiphenylsiloxy))-2,4-((R)-benzylidenedioxy)-10,12-(isopropylidenedioxy)-3,5,9,11,13-pentamethyltetradecan-7-on

: 251099-50-0
(2R,3S,4S,5R,6S,9S,10S,11R,12R,13S)-6-(tert-butyldimethylsiloxy)-14-((tert-butyldiphenylsiloxy))-2,4-((R)-benzylidenedioxy)-10,12-(isopropylidenedioxy)-7-methylene-3,5,9,11,13-pentamethyltetradecane

Guidance literature:: With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at 50 ℃; for 2h;
DOI:10.1021/ja020853m

Reference yield: 82.0%

: 251099-27-1
(2R,3R,4S,5R,6S)-1-iodo-7-(tert-butyldiphenylsilyloxy)-3,5-(isopropylidenedioxy)-2,4,6-trimethyl-heptane

: 251099-49-7
(3S,4R,5S,6S,7R)-3-(tert-butyldimethylsilyloxy)-5,7-((R)-benzylidenedioxy)-4,6-dimethyl-1-octene-2-yl-trifluoromethanesulfonate

: 251099-50-0
(2R,3S,4S,5R,6S,9S,10S,11R,12R,13S)-6-(tert-butyldimethylsiloxy)-14-((tert-butyldiphenylsiloxy))-2,4-((R)-benzylidenedioxy)-10,12-(isopropylidenedioxy)-7-methylene-3,5,9,11,13-pentamethyltetradecane

Guidance literature:: (2R,3R,4S,5R,6S)-1-iodo-7-(tert-butyldiphenylsilyloxy)-3,5-(isopropylidenedioxy)-2,4,6-trimethyl-heptane; With tert.-butyl lithium; In tetrahydrofuran; at -78 ℃; for 0.5h;

With zinc(II) chloride; In tetrahydrofuran; at -78 ℃; for 0.25h;

(3S,4R,5S,6S,7R)-3-(tert-butyldimethylsilyloxy)-5,7-((R)-benzylidenedioxy)-4,6-dimethyl-1-octene-2-yl-trifluoromethanesulfonate; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; lithium chloride; at -78 - 20 ℃; for 0.75h;
DOI:10.1021/ja992370x

Reference yield:

: 184528-51-6
(5R,6S,7S)-(E)-methyl-8-[(tert-butyldiphenylsilyl)oxy]-6-hydroxy-5,7-dimethyl-3-octenoate

: 251099-50-0
(2R,3S,4S,5R,6S,9S,10S,11R,12R,13S)-6-(tert-butyldimethylsiloxy)-14-((tert-butyldiphenylsiloxy))-2,4-((R)-benzylidenedioxy)-10,12-(isopropylidenedioxy)-7-methylene-3,5,9,11,13-pentamethyltetradecane

Guidance literature:: Multi-step reaction with 11 steps

1.1: 92 percent / aq. HCl / methanol / 20 °C

2.1: 2,4-lutidine / CH₂Cl₂ / -78 °C

3.1: O₃ / methanol; pyridine

3.2: Me₂S / methanol; pyridine

4.1: 87 percent / TiCl₄ / CH₂Cl₂ / -78 - -30 °C

5.1: HF*pyridine; pyridine / tetrahydrofuran / 1 h / 0 °C

6.1: 2.29 g / imidazole / dimethylformamide / 4 h / 20 °C

7.1: 99 percent / p-toluenesulfonic acid monohydrate / 0.75 h / 20 °C

8.1: O₃; pyridine / methanol / -78 °C

8.2: Me₂S / methanol / 4 h / -78 - 20 °C

9.1: 1.09 g / NaBH₄ / methanol / 0.5 h / 0 °C

10.1: 98 percent / I₂; triphenylphosphine; imidazole / CH₂Cl₂ / 12.25 h / 0 - 20 °C

11.1: t-BuLi / pentane / 0.5 h / -78 - 20 °C

11.2: ZnCl₂ / tetrahydrofuran; pentane / 0.25 h / -78 °C

11.3: 82 percent / Pd(PPh₃)4; LiCl / tetrahydrofuran; pentane / -78 - 0 °C

With pyridine; 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; 2,4-lutidine; iodine; tert.-butyl lithium; titanium tetrachloride; pyridine hydrogenfluoride; ozone; triphenylphosphine; toluene-4-sulfonic acid; In tetrahydrofuran; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; pentane;
DOI:10.1021/ja020853m