S-phenyl (2R,3R,4R,5R,6E)-5-{[(tert-butyl)dimethylsilyl]oxy}-3-hydroxy-2-methoxy-8-methyl-4-[(phenyl)methoxy]non-6-enethioate

Base Information

Chemical Name:S-phenyl (2R,3R,4R,5R,6E)-5-{[(tert-butyl)dimethylsilyl]oxy}-3-hydroxy-2-methoxy-8-methyl-4-[(phenyl)methoxy]non-6-enethioate
CAS No.:442913-22-6
Molecular Formula:C₃₀H₄₄O₅SSi
Molecular Weight:544.828
Hs Code.:

Synonyms:S-phenyl (2R,3R,4R,5R,6E)-5-{[(tert-butyl)dimethylsilyl]oxy}-3-hydroxy-2-methoxy-8-methyl-4-[(phenyl)methoxy]non-6-enethioate

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Chemical Property of S-phenyl (2R,3R,4R,5R,6E)-5-{[(tert-butyl)dimethylsilyl]oxy}-3-hydroxy-2-methoxy-8-methyl-4-[(phenyl)methoxy]non-6-enethioate

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Technology Process of S-phenyl (2R,3R,4R,5R,6E)-5-{[(tert-butyl)dimethylsilyl]oxy}-3-hydroxy-2-methoxy-8-methyl-4-[(phenyl)methoxy]non-6-enethioate

There total 10 articles about S-phenyl (2R,3R,4R,5R,6E)-5-{[(tert-butyl)dimethylsilyl]oxy}-3-hydroxy-2-methoxy-8-methyl-4-[(phenyl)methoxy]non-6-enethioate 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: 73.0%

: 547742-43-8
[2-methoxy-1-(phenylsulfanyl)ethenyl]trimethylsilane

: 442913-27-1
(2S,3R,4E)-3-{[(tert-butyl)dimethylsilyl]oxy}-6-methyl-2-[(phenyl)methoxy]hept-4-enal

: S-phenyl (4S,5R,6E)-5-tertbutyldimethylsilyloxy-3-hydroxy-2-methoxy-8-methyl-4-phenylmethoxynon-6-enethioate

: 442913-22-6
S-phenyl (2R,3R,4R,5R,6E)-5-{[(tert-butyl)dimethylsilyl]oxy}-3-hydroxy-2-methoxy-8-methyl-4-[(phenyl)methoxy]non-6-enethioate

Guidance literature:: With tin(IV) chloride; In dichloromethane; at -78 ℃; for 0.5h;
DOI:10.1021/ol026101e

Reference yield: 73.0%

: 547742-43-8
[2-methoxy-1-(phenylsulfanyl)ethenyl]trimethylsilane

: 442913-27-1
(2S,3R,4E)-3-{[(tert-butyl)dimethylsilyl]oxy}-6-methyl-2-[(phenyl)methoxy]hept-4-enal

: 442913-22-6
S-phenyl (2R,3R,4R,5R,6E)-5-{[(tert-butyl)dimethylsilyl]oxy}-3-hydroxy-2-methoxy-8-methyl-4-[(phenyl)methoxy]non-6-enethioate

Guidance literature:: [2-methoxy-1-(phenylsulfanyl)ethenyl]trimethylsilane; With tin(IV) chloride; In n-heptane; dichloromethane; at -78 ℃; for 0.5h;

(2S,3R,4E)-3-{[(tert-butyl)dimethylsilyl]oxy}-6-methyl-2-[(phenyl)methoxy]hept-4-enal; In n-heptane; dichloromethane; at -78 ℃; for 4h;
DOI:10.1002/hlca.200290026

Reference yield:

: 24502-08-7
(E)-4-methylpent-2-enal

: 442913-22-6
S-phenyl (2R,3R,4R,5R,6E)-5-{[(tert-butyl)dimethylsilyl]oxy}-3-hydroxy-2-methoxy-8-methyl-4-[(phenyl)methoxy]non-6-enethioate

Guidance literature:: Multi-step reaction with 5 steps

1.1: DIPEA; diethylboron triflate / CH₂Cl₂ / 1 h / -78 °C

1.2: 85 percent / CH₂Cl₂ / 9 h / -50 °C

2.1: 94 percent / imidazole / dimethylformamide / 13 h / 20 °C

3.1: BiLi / tetrahydrofuran; hexane / 0.33 h / -78 °C

3.2: 93 percent / tetrahydrofuran; hexane / 5 h / -40 °C

4.1: 91 percent / DIBAL / toluene / 0.5 h / -78 °C

5.1: SnCl₄ / heptane; CH₂Cl₂ / 0.5 h / -78 °C

5.2: 73 percent / heptane; CH₂Cl₂ / 4 h / -78 °C

With 1H-imidazole; n-butyllithium; tin(IV) chloride; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; diethylboron trifluoromethanesulfonate; In tetrahydrofuran; hexane; n-heptane; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1002/hlca.200290026