(Z)-6-((S)-2-Benzyloxymethyl-1-methyl-cyclopent-2-enyl)-2-hydroxy-2-((R)-3-hydroxy-2-methyl-propyl)-4-methyl-hex-4-enenitrile

Base Information

Chemical Name:(Z)-6-((S)-2-Benzyloxymethyl-1-methyl-cyclopent-2-enyl)-2-hydroxy-2-((R)-3-hydroxy-2-methyl-propyl)-4-methyl-hex-4-enenitrile
CAS No.:871823-42-6
Molecular Formula:C₂₅H₃₅NO₃
Molecular Weight:397.558
Hs Code.:

Synonyms:(Z)-6-((S)-2-Benzyloxymethyl-1-methyl-cyclopent-2-enyl)-2-hydroxy-2-((R)-3-hydroxy-2-methyl-propyl)-4-methyl-hex-4-enenitrile

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (Z)-6-((S)-2-Benzyloxymethyl-1-methyl-cyclopent-2-enyl)-2-hydroxy-2-((R)-3-hydroxy-2-methyl-propyl)-4-methyl-hex-4-enenitrile

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Technology Process of (Z)-6-((S)-2-Benzyloxymethyl-1-methyl-cyclopent-2-enyl)-2-hydroxy-2-((R)-3-hydroxy-2-methyl-propyl)-4-methyl-hex-4-enenitrile

There total 17 articles about (Z)-6-((S)-2-Benzyloxymethyl-1-methyl-cyclopent-2-enyl)-2-hydroxy-2-((R)-3-hydroxy-2-methyl-propyl)-4-methyl-hex-4-enenitrile 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: 81.0%

: (Z)-6-((S)-2-Benzyloxymethyl-1-methyl-cyclopent-2-enyl)-2-((E)-2-ethoxy-vinyloxy)-4-methyl-2-[(R)-2-methyl-3-(tetrahydro-pyran-2-yloxy)-propyl]-hex-4-enenitrile

: 871823-42-6
(Z)-6-((S)-2-Benzyloxymethyl-1-methyl-cyclopent-2-enyl)-2-hydroxy-2-((R)-3-hydroxy-2-methyl-propyl)-4-methyl-hex-4-enenitrile

Guidance literature:: With methanol; pyridinium p-toluenesulfonate;
DOI:10.1016/j.tetlet.2005.09.106

Reference yield:

: (2S,3S)-2-(2,3-Dihydroxy-propyl)-3-hydroxy-2-methyl-cyclopentanone

: 871823-42-6
(Z)-6-((S)-2-Benzyloxymethyl-1-methyl-cyclopent-2-enyl)-2-hydroxy-2-((R)-3-hydroxy-2-methyl-propyl)-4-methyl-hex-4-enenitrile

Guidance literature:: Multi-step reaction with 11 steps

1.1: BF₃*Et₂O

2.1: 92 percent / Raney nickel

3.1: 100 percent / Dess-Martin periodinane

4.2: 86 percent / LDA

5.1: 95 percent / NaH

6.1: 100 percent / HIO₄ / ethyl acetate

7.1: 91 percent / NaH

8.1: 97 percent / MsCl; Et₃N; LiCl

9.1: 49 percent / NaHDMS

10.1: 81 percent / CH₃OH / PPTS

With methanol; boron trifluoride diethyl etherate; sodium hexamethyldisilazane; sodium hydride; Dess-Martin periodane; methanesulfonyl chloride; periodic acid; triethylamine; lithium chloride; pyridinium p-toluenesulfonate; nickel; In ethyl acetate; 8.1: Horner-Emmons reaction;
DOI:10.1016/j.tetlet.2005.09.106

Reference yield:

: 871823-25-5
(S)-2-(2,2-Dimethyl-[1,3]dioxolan-4-ylmethyl)-2-methyl-cyclopentanone

: 871823-42-6
(Z)-6-((S)-2-Benzyloxymethyl-1-methyl-cyclopent-2-enyl)-2-hydroxy-2-((R)-3-hydroxy-2-methyl-propyl)-4-methyl-hex-4-enenitrile

Guidance literature:: Multi-step reaction with 7 steps

1.2: 86 percent / LDA

2.1: 95 percent / NaH

3.1: 100 percent / HIO₄ / ethyl acetate

4.1: 91 percent / NaH

5.1: 97 percent / MsCl; Et₃N; LiCl

6.1: 49 percent / NaHDMS

7.1: 81 percent / CH₃OH / PPTS

With methanol; sodium hexamethyldisilazane; sodium hydride; methanesulfonyl chloride; periodic acid; triethylamine; lithium chloride; pyridinium p-toluenesulfonate; In ethyl acetate; 4.1: Horner-Emmons reaction;
DOI:10.1016/j.tetlet.2005.09.106