(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

Base Information

Chemical Name:(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
CAS No.:1357075-59-2
Molecular Formula:C₃₀H₄₈O₃SSi
Molecular Weight:516.861
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 3 articles about (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 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: 97.0%

: 1357075-57-0
(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

: 74-88-4
methyl iodide

: 1357075-59-2
(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

Guidance literature:: With sodium hydride; In tetrahydrofuran; mineral oil; at 20 ℃; for 2h; optical yield given as %de; Inert atmosphere;
DOI:10.1021/jo2016554

Reference yield:

: 682352-10-9
(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

: 1357075-59-2
(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

Guidance literature:: Multi-step reaction with 2 steps

1: tetrahydrofuran / 2 h / -78 °C / Inert atmosphere

2: sodium hydride / tetrahydrofuran; mineral oil / 2 h / 20 °C / Inert atmosphere

With sodium hydride; In tetrahydrofuran; mineral oil;
DOI:10.1021/jo2016554

Reference yield:

: 682352-11-0
(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

: 1357075-59-2
(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

Guidance literature:: Multi-step reaction with 2 steps

1: tetrahydrofuran / 2 h / -78 °C / Inert atmosphere

2: sodium hydride / tetrahydrofuran; mineral oil / 2 h / 20 °C / Inert atmosphere

With sodium hydride; In tetrahydrofuran; mineral oil;
DOI:10.1021/jo2016554