(2R,3R,4S,7S)-allyl-3-((3R,4R)-3,4-bis(tert-butyldimethylsilyloxy)pentanoyloxy)-7-(3-(tert-butyldimethylsilyloxy)phenyl)-7-methoxy-2,4-dimethylheptanoate

Base Information

Chemical Name:(2R,3R,4S,7S)-allyl-3-((3R,4R)-3,4-bis(tert-butyldimethylsilyloxy)pentanoyloxy)-7-(3-(tert-butyldimethylsilyloxy)phenyl)-7-methoxy-2,4-dimethylheptanoate
CAS No.:1450899-63-4
Molecular Formula:C₄₂H₇₈O₈Si₃
Molecular Weight:795.333
Hs Code.:

(2R,3R,4S,7S)-allyl-3-((3R,4R)-3,4-bis(tert-butyldimethylsilyloxy)pentanoyloxy)-7-(3-(tert-butyldimethylsilyloxy)phenyl)-7-methoxy-2,4-dimethylheptanoate

Synonyms:(2R,3R,4S,7S)-allyl-3-((3R,4R)-3,4-bis(tert-butyldimethylsilyloxy)pentanoyloxy)-7-(3-(tert-butyldimethylsilyloxy)phenyl)-7-methoxy-2,4-dimethylheptanoate

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Chemical Property of (2R,3R,4S,7S)-allyl-3-((3R,4R)-3,4-bis(tert-butyldimethylsilyloxy)pentanoyloxy)-7-(3-(tert-butyldimethylsilyloxy)phenyl)-7-methoxy-2,4-dimethylheptanoate

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Technology Process of (2R,3R,4S,7S)-allyl-3-((3R,4R)-3,4-bis(tert-butyldimethylsilyloxy)pentanoyloxy)-7-(3-(tert-butyldimethylsilyloxy)phenyl)-7-methoxy-2,4-dimethylheptanoate

There total 12 articles about (2R,3R,4S,7S)-allyl-3-((3R,4R)-3,4-bis(tert-butyldimethylsilyloxy)pentanoyloxy)-7-(3-(tert-butyldimethylsilyloxy)phenyl)-7-methoxy-2,4-dimethylheptanoate 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: 40.0%

: 1450899-61-2
(2R,3R,4S,7S)-allyl-7-(3-(tert-butyldimethylsilyloxy)phenyl)-3-hydroxy-7-methoxy-2,4-dimethylheptanoate

: 1450899-57-6
(+)-(3R,4R)-3,4-bis((tert-butyldimethylsilyl)oxy)pentanoic acid

: 1450899-63-4
(2R,3R,4S,7S)-allyl-3-((3R,4R)-3,4-bis(tert-butyldimethylsilyloxy)pentanoyloxy)-7-(3-(tert-butyldimethylsilyloxy)phenyl)-7-methoxy-2,4-dimethylheptanoate

Guidance literature:: (+)-(3R,4R)-3,4-bis((tert-butyldimethylsilyl)oxy)pentanoic acid; With dmap; 2,4,6-trichlorobenzoyl chloride; In toluene; at 20 ℃; for 2h; Inert atmosphere;

(2R,3R,4S,7S)-allyl-7-(3-(tert-butyldimethylsilyloxy)phenyl)-3-hydroxy-7-methoxy-2,4-dimethylheptanoate; In toluene; at 20 ℃; for 4h; Inert atmosphere;
DOI:10.1021/jo401248n

Reference yield:

: 1450899-59-8
(2R,3R,4S,7S)-7-(3-(tert-butyldimethylsilyloxy)phenyl)-3-hydroxy-7-methoxy-2,4-dimethylheptanoic acid

: 1450899-63-4
(2R,3R,4S,7S)-allyl-3-((3R,4R)-3,4-bis(tert-butyldimethylsilyloxy)pentanoyloxy)-7-(3-(tert-butyldimethylsilyloxy)phenyl)-7-methoxy-2,4-dimethylheptanoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 48 h / 0 - 20 °C / Inert atmosphere

2.1: dmap; 2,4,6-trichlorobenzoyl chloride / toluene / 2 h / 20 °C / Inert atmosphere

2.2: 4 h / 20 °C / Inert atmosphere

With dmap; 2,4,6-trichlorobenzoyl chloride; potassium carbonate; In N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo401248n

Reference yield:

: 96013-95-5
3-(tert-butyl-dimethyl-sylanyloxy)benzaldehyde

: 1450899-63-4
(2R,3R,4S,7S)-allyl-3-((3R,4R)-3,4-bis(tert-butyldimethylsilyloxy)pentanoyloxy)-7-(3-(tert-butyldimethylsilyloxy)phenyl)-7-methoxy-2,4-dimethylheptanoate

Guidance literature:: Multi-step reaction with 11 steps

1.1: tetrahydrofuran / 1.08 h / -10 °C / Inert atmosphere

2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide; dichloromethane / 3.08 h / 0 - 20 °C / Inert atmosphere

3.1: titanium tetrachloride; titanium(IV) isopropylate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.58 h / Inert atmosphere

3.2: 0.58 h / -5 °C / Inert atmosphere

4.1: dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / dichloromethane; toluene / 5 h / -5 - 0 °C / Inert atmosphere

5.1: 2,6-di-tert-butyl-pyridine / dichloromethane / 18.08 h / 0 - 20 °C / Inert atmosphere

6.1: sodium tetrahydroborate / tetrahydrofuran; water / 14 h / 20 °C

7.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide; dichloromethane / 3.08 h / 0 - 20 °C / Inert atmosphere

8.1: D-Prolin / N,N-dimethyl-formamide / 48 h / 2 °C / Inert atmosphere

9.1: 2-methyl-but-2-ene; sodium chlorite; sodium dihydrogenphosphate / water; tert-butyl alcohol / 1 h / 0 °C

10.1: potassium carbonate / N,N-dimethyl-formamide / 48 h / 0 - 20 °C / Inert atmosphere

11.1: dmap; 2,4,6-trichlorobenzoyl chloride / toluene / 2 h / 20 °C / Inert atmosphere

11.2: 4 h / 20 °C / Inert atmosphere

With titanium(IV) isopropylate; dmap; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; 2,6-di-tert-butyl-pyridine; 2-methyl-but-2-ene; dimethylsulfide borane complex; 2,4,6-trichlorobenzoyl chloride; titanium tetrachloride; potassium carbonate; N-ethyl-N,N-diisopropylamine; D-Prolin; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
DOI:10.1021/jo401248n