[(1S,2S,4R,6R,7S)-10,10-Dimethyl-4-((E)-styryl)-3,5-dioxa-tricyclo[5.2.1.0^2,6]dec-1-yl]-methanesulfonic acid phenyl ester

Base Information

• Chemical Name: [(1S,2S,4R,6R,7S)-10,10-Dimethyl-4-((E)-styryl)-3,5-dioxa-tricyclo[5.2.1.0^2,6]dec-1-yl]-methanesulfonic acid phenyl ester
• CAS No.: 220049-50-3
• Molecular Formula: C₂₅H₂₈O₅S
• Molecular Weight: 440.56

Synonyms:[(1S,2S,4R,6R,7S)-10,10-Dimethyl-4-((E)-styryl)-3,5-dioxa-tricyclo[5.2.1.0^2,6]dec-1-yl]-methanesulfonic acid phenyl ester

Chemical Property of [(1S,2S,4R,6R,7S)-10,10-Dimethyl-4-((E)-styryl)-3,5-dioxa-tricyclo[5.2.1.0^2,6]dec-1-yl]-methanesulfonic acid phenyl ester

Chemical Property:

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Technology Process of [(1S,2S,4R,6R,7S)-10,10-Dimethyl-4-((E)-styryl)-3,5-dioxa-tricyclo[5.2.1.0^2,6]dec-1-yl]-methanesulfonic acid phenyl ester

There total 5 articles about [(1S,2S,4R,6R,7S)-10,10-Dimethyl-4-((E)-styryl)-3,5-dioxa-tricyclo[5.2.1.0^2,6]dec-1-yl]-methanesulfonic acid phenyl ester 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:

(1S)-(7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl)methane sulfonic acid phenyl ester (108885-08-1) → [(1S,2S,4R,6R,7S)-10,10-Dimethyl-4-((E)-styryl)-3,5-dioxa-tricyclo[5.2.1.02,6]dec-1-yl]-methanesulfonic acid phenyl ester (220049-50-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 48 percent / H₂SeO₃ / dioxane

2: 51 percent / NaBH₄ / methanol

3: TsOH, MgSO₄ / benzene

With sodium tetrahydroborate; selenious acid; magnesium sulfate; toluene-4-sulfonic acid; In 1,4-dioxane; methanol; benzene;

DOI:10.1039/a806867d

Reference yield:

Camphorsulfonyl chloride (21286-54-4) → [(1S,2S,4R,6R,7S)-10,10-Dimethyl-4-((E)-styryl)-3,5-dioxa-tricyclo[5.2.1.02,6]dec-1-yl]-methanesulfonic acid phenyl ester (220049-50-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 81 percent / pyridine / 0 °C

2: 48 percent / H₂SeO₃ / dioxane

3: 51 percent / NaBH₄ / methanol

4: TsOH, MgSO₄ / benzene

With pyridine; sodium tetrahydroborate; selenious acid; magnesium sulfate; toluene-4-sulfonic acid; In 1,4-dioxane; methanol; benzene;

DOI:10.1039/a806867d

Reference yield:

((1S,4S)-7,7-Dimethyl-2,3-dioxo-bicyclo[2.2.1]hept-1-yl)-methanesulfonic acid phenyl ester (220049-46-7) → [(1S,2S,4R,6R,7S)-10,10-Dimethyl-4-((E)-styryl)-3,5-dioxa-tricyclo[5.2.1.02,6]dec-1-yl]-methanesulfonic acid phenyl ester (220049-50-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 51 percent / NaBH₄ / methanol

2: TsOH, MgSO₄ / benzene

With sodium tetrahydroborate; magnesium sulfate; toluene-4-sulfonic acid; In methanol; benzene;

DOI:10.1039/a806867d

upstream raw materials:

(E)-3-phenylpropenal

((1S,2S,3R,4S)-2,3-Dihydroxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-yl)-methanesulfonic acid phenyl ester

Camphorsulfonyl chloride

(1S)-(7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl)methane sulfonic acid phenyl ester

Downstream raw materials:

[(1S,2S,4R,6R,7S)-10,10-Dimethyl-4-((1R,2R)-2-phenyl-cyclopropyl)-3,5-dioxa-tricyclo[5.2.1.0^2,6]dec-1-yl]-methanesulfonic acid phenyl ester

[(1S,2S,4R,6R,7S)-10,10-Dimethyl-4-((1R,2R)-2-propyl-cyclopropyl)-3,5-dioxa-tricyclo[5.2.1.0^2,6]dec-1-yl]-methanesulfonic acid phenyl ester

[(1S,2S,4R,6R,7S)-10,10-Dimethyl-4-((1R,2R)-2-methyl-cyclopropyl)-3,5-dioxa-tricyclo[5.2.1.0^2,6]dec-1-yl]-methanesulfonic acid phenyl ester

[(1S,2S,4R,6R,7S)-10,10-Dimethyl-4-((E)-pent-1-enyl)-3,5-dioxa-tricyclo[5.2.1.0^2,6]dec-1-yl]-methanesulfonic acid phenyl ester

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