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

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Chemical Name:S-phenyl (2R,3R,4R,5R,6E)-5-{[(tert-butyl)dimethylsilyl]oxy}-3-hydroxy-2-methoxy-8-methyl-4-[(2-naphthyl)methoxy]non-6-enethioate
CAS No.:442913-36-2
Molecular Formula:C₃₄H₄₆O₅SSi
Molecular Weight:594.888
Hs Code.:

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

There total 9 articles about S-phenyl (2R,3R,4R,5R,6E)-5-{[(tert-butyl)dimethylsilyl]oxy}-3-hydroxy-2-methoxy-8-methyl-4-[(2-naphthyl)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: 62.0%

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

: 442913-39-5
(2S,3R,4E)-3-{[(tert-butyl)dimethylsilyl]oxy}-6-methyl-2-[(2-naphthyl)methoxy]hept-4-enal

: 442913-36-2
S-phenyl (2R,3R,4R,5R,6E)-5-{[(tert-butyl)dimethylsilyl]oxy}-3-hydroxy-2-methoxy-8-methyl-4-[(2-naphthyl)methoxy]non-6-enethioate

Guidance literature:: [2-methoxy-1-(phenylsulfanyl)ethenyl]trimethylsilane; With tin(IV) chloride; In n-heptane; dichloromethane; at -78 ℃; for 0.75h;

(2S,3R,4E)-3-{[(tert-butyl)dimethylsilyl]oxy}-6-methyl-2-[(2-naphthyl)methoxy]hept-4-enal; In n-heptane; dichloromethane; at -78 ℃; for 1.5h;
DOI:10.1002/hlca.200290026

Reference yield:

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

: 442913-36-2
S-phenyl (2R,3R,4R,5R,6E)-5-{[(tert-butyl)dimethylsilyl]oxy}-3-hydroxy-2-methoxy-8-methyl-4-[(2-naphthyl)methoxy]non-6-enethioate

Guidance literature:: Multi-step reaction with 4 steps

1.1: iPrNEt; Et₂BOTf / CH₂Cl₂ / -78 °C / 1 Torr

1.2: tetrahydrofuran / 23 h / -40 °C

1.3: 70 percent / 1H-imidazole / CH₂Cl₂ / 11 h / 20 °C

2.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.2: 91 percent / tetrahydrofuran / 10 h / -40 °C

3.1: 99 percent / DIBAL / toluene / 0.75 h / -78 °C

4.1: SnCl₄ / heptane; CH₂Cl₂ / 0.75 h / -78 °C

4.2: 62 percent / heptane; CH₂Cl₂ / 1.5 h / -78 °C

With n-butyllithium; tin(IV) chloride; diisobutylaluminium hydride; N-isopropylethylamine; diethylboron trifluoromethanesulfonate; In tetrahydrofuran; hexane; n-heptane; dichloromethane; toluene;
DOI:10.1002/hlca.200290026

Reference yield:

: 72867-24-4
S-phenyl 2-methoxyethanethionate

: 442913-36-2
S-phenyl (2R,3R,4R,5R,6E)-5-{[(tert-butyl)dimethylsilyl]oxy}-3-hydroxy-2-methoxy-8-methyl-4-[(2-naphthyl)methoxy]non-6-enethioate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 76 percent / Et₃N / CH₂Cl₂ / 17 h / -10 °C

2.1: SnCl₄ / heptane; CH₂Cl₂ / 0.75 h / -78 °C

2.2: 62 percent / heptane; CH₂Cl₂ / 1.5 h / -78 °C

With tin(IV) chloride; triethylamine; In n-heptane; dichloromethane;
DOI:10.1002/hlca.200290026