(1S,2R,3S,5R)-2-(O-tert-butyldimethylsilyloxymethylen)-6,6-dimethyl-3-[(1R,2R)-1-ethoxy-2-phenyl-2-hydroxy-3-pentyn-1-sulfanyl]bicyclo[3.1.1]heptane

Base Information

• Chemical Name: (1S,2R,3S,5R)-2-(O-tert-butyldimethylsilyloxymethylen)-6,6-dimethyl-3-[(1R,2R)-1-ethoxy-2-phenyl-2-hydroxy-3-pentyn-1-sulfanyl]bicyclo[3.1.1]heptane
• CAS No.: 1357075-57-0
• Molecular Formula: C₂₉H₄₆O₃SSi
• Molecular Weight: 502.834

Synonyms:(1S,2R,3S,5R)-2-(O-tert-butyldimethylsilyloxymethylen)-6,6-dimethyl-3-[(1R,2R)-1-ethoxy-2-phenyl-2-hydroxy-3-pentyn-1-sulfanyl]bicyclo[3.1.1]heptane

Chemical Property of (1S,2R,3S,5R)-2-(O-tert-butyldimethylsilyloxymethylen)-6,6-dimethyl-3-[(1R,2R)-1-ethoxy-2-phenyl-2-hydroxy-3-pentyn-1-sulfanyl]bicyclo[3.1.1]heptane

Chemical Property:

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Technology Process of (1S,2R,3S,5R)-2-(O-tert-butyldimethylsilyloxymethylen)-6,6-dimethyl-3-[(1R,2R)-1-ethoxy-2-phenyl-2-hydroxy-3-pentyn-1-sulfanyl]bicyclo[3.1.1]heptane

There total 2 articles about (1S,2R,3S,5R)-2-(O-tert-butyldimethylsilyloxymethylen)-6,6-dimethyl-3-[(1R,2R)-1-ethoxy-2-phenyl-2-hydroxy-3-pentyn-1-sulfanyl]bicyclo[3.1.1]heptane 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: 96.0%

1-propynylmagnesium bromide (16466-97-0,13254-27-8) + (1S,2R,3S,5R,2'R)-6,6-dimethyl-3-(2'-ethoxy-1'-phenyl-1'-oxo-2'-ethylsulfanyl)-2-(O-t-butyl-dimethylsilyl-hydroxymethyl)-bicyclo[3.1.1]heptane (682352-11-0) → (1S,2R,3S,5R)-2-(O-tert-butyldimethylsilyloxymethylen)-6,6-dimethyl-3-[(1R,2R)-1-ethoxy-2-phenyl-2-hydroxy-3-pentyn-1-sulfanyl]bicyclo[3.1.1]heptane (1357075-57-0)

Guidance literature:

In tetrahydrofuran; at -78 ℃; for 2h; optical yield given as %de; Inert atmosphere;

DOI:10.1021/jo2016554

Reference yield:

1-propynylmagnesium bromide (16466-97-0,13254-27-8) + (1S,2R,3S,5R,2'S)-6,6-dimethyl-3-(2'-ethoxy-1'-phenyl-1'-oxo-2'-ethylsulfanyl)-2-(O-t-butyl-dimethylsilyl-hydroxymethyl)-bicyclo[3.1.1]heptane (682352-10-9) + (1S,2R,3S,5R,2'R)-6,6-dimethyl-3-(2'-ethoxy-1'-phenyl-1'-oxo-2'-ethylsulfanyl)-2-(O-t-butyl-dimethylsilyl-hydroxymethyl)-bicyclo[3.1.1]heptane (682352-11-0) → (1S,2R,3S,5R)-2-(O-tert-butyldimethylsilyloxymethylen)-6,6-dimethyl-3-[(1S,2S)-1-ethoxy-2-phenyl-2-hydroxy-3-pentyn-1-sulfanyl]bicyclo[3.1.1]heptane (1357075-58-1) + (1S,2R,3S,5R)-2-(O-tert-butyldimethylsilyloxymethylen)-6,6-dimethyl-3-[(1R,2R)-1-ethoxy-2-phenyl-2-hydroxy-3-pentyn-1-sulfanyl]bicyclo[3.1.1]heptane (1357075-57-0)

Guidance literature:

In ethanol; for 72h; pH=9; aq. buffer;

DOI:10.1039/c2ob06715c

Reference yield: 97.0%

(1S,2R,3S,5R)-2-(O-tert-butyldimethylsilyloxymethylen)-6,6-dimethyl-3-[(1R,2R)-1-ethoxy-2-phenyl-2-hydroxy-3-pentyn-1-sulfanyl]bicyclo[3.1.1]heptane (1357075-57-0) + methyl iodide (74-88-4) → (1S,2R,3S,5R)-2-(O-tert-butyldimethylsilyloxymethylen)-6,6-dimethyl-3-[(1R,2R)-2-methoxy-1-ethoxy-2-phenyl-3-pentyn-1-sulfanyl]bicyclo[3.1.1]heptane (1357075-59-2)

Guidance literature:

With sodium hydride; In tetrahydrofuran; mineral oil; at 20 ℃; for 2h; optical yield given as %de; Inert atmosphere;

DOI:10.1021/jo2016554

upstream raw materials:

1-propynylmagnesium bromide

(1S,2R,3S,5R,2'S)-6,6-dimethyl-3-(2'-ethoxy-1'-phenyl-1'-oxo-2'-ethylsulfanyl)-2-(O-t-butyl-dimethylsilyl-hydroxymethyl)-bicyclo[3.1.1]heptane

(1S,2R,3S,5R,2'R)-6,6-dimethyl-3-(2'-ethoxy-1'-phenyl-1'-oxo-2'-ethylsulfanyl)-2-(O-t-butyl-dimethylsilyl-hydroxymethyl)-bicyclo[3.1.1]heptane

Downstream raw materials:

(1R,2S)-1-(2-phenyl)cyclohexanyl (R)-2-methoxy-2-phenylpent-3-ynoate

(1R)-1-(1-phenyl)ethyl (R)-2-methoxy-2-phenylpent-3-ynoate

(1R,2S,5R)-1-isopulegoyl (R)-2-methoxy-2-phenylpent-3-ynoate

(1R,2S,5R)-1-isopulegoyl (S)-2-methoxy-2-phenylpent-3-ynoate

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