(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

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)-3,5,9,11,13-pentamethyltetradecan-7-on
CAS No.:476622-77-2
Molecular Formula:C₅₁H₇₈O₇Si₂
Molecular Weight:859.347
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)-3,5,9,11,13-pentamethyltetradecan-7-on

Synonyms:(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

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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)-3,5,9,11,13-pentamethyltetradecan-7-on

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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)-3,5,9,11,13-pentamethyltetradecan-7-on

There total 23 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)-3,5,9,11,13-pentamethyltetradecan-7-on 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:

: 476622-76-1
(2R,3S,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-6-{(4S,5R,6R)-6-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-2-((2R,4S,5S,6R)-5,6-dimethyl-2-phenyl-[1,3]dioxan-4-yl)-heptan-4-ol

: 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

Guidance literature:: With pyridine; Dess-Martin periodane; In dichloromethane; at 0 - 20 ℃; for 6h;
DOI:10.1021/ja020853m

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 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

Guidance literature:: Multi-step reaction with 7 steps

1.1: 2.29 g / imidazole / dimethylformamide / 4 h / 20 °C

2.1: 99 percent / p-toluenesulfonic acid monohydrate / 0.75 h / 20 °C

3.1: O₃; pyridine / methanol / -78 °C

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

4.1: 1.09 g / NaBH₄ / methanol / 0.5 h / 0 °C

5.1: 98 percent / I₂; triphenylphosphine; imidazole / CH₂Cl₂ / 12.25 h / 0 - 20 °C

6.1: t-BuLi / pentane; diethyl ether / 0.08 h / -78 °C

6.2: pentane; diethyl ether / 0.5 h / -78 °C

7.1: 79 mg / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 6 h / 0 - 20 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; iodine; tert.-butyl lithium; Dess-Martin periodane; ozone; triphenylphosphine; toluene-4-sulfonic acid; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; pentane;
DOI:10.1021/ja020853m

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 12 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; diethyl ether / 0.08 h / -78 °C

11.2: pentane; diethyl ether / 0.5 h / -78 °C

12.1: 79 mg / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 6 h / 0 - 20 °C

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