(+)-(2R,3R,4R,5S,S_S)-3,4-epoxy-4-(p-tolylsulfinyl)-5-vinyl-tetrahydrofuran-2-methanol

Base Information

• Chemical Name: (+)-(2R,3R,4R,5S,S_S)-3,4-epoxy-4-(p-tolylsulfinyl)-5-vinyl-tetrahydrofuran-2-methanol
• CAS No.: 219776-33-7
• Molecular Formula: C₁₄H₁₆O₄S
• Molecular Weight: 280.345

Synonyms:(+)-(2R,3R,4R,5S,S_S)-3,4-epoxy-4-(p-tolylsulfinyl)-5-vinyl-tetrahydrofuran-2-methanol

Chemical Property of (+)-(2R,3R,4R,5S,S_S)-3,4-epoxy-4-(p-tolylsulfinyl)-5-vinyl-tetrahydrofuran-2-methanol

Chemical Property:

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Technology Process of (+)-(2R,3R,4R,5S,S_S)-3,4-epoxy-4-(p-tolylsulfinyl)-5-vinyl-tetrahydrofuran-2-methanol

There total 6 articles about (+)-(2R,3R,4R,5S,S_S)-3,4-epoxy-4-(p-tolylsulfinyl)-5-vinyl-tetrahydrofuran-2-methanol 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: 47.0%

(+)-cis-4-(p-tolylsulfinyl)-5-vinyl-2,5-dihydrofuran-2-methanol (219776-32-6) → (+)-(2R,3R,4R,5S,SS)-3,4-epoxy-4-(p-tolylsulfinyl)-5-vinyl-tetrahydrofuran-2-methanol (219776-33-7) + (2R,3R,4R,5S)-3,4-epoxy-2-(p-tolylsulfonyl)-5-vinyl-tetrahydrofuran-2-methanol (219776-34-8)

Guidance literature:

With tert.-butylhydroperoxide; potassium hydride; In tetrahydrofuran; at -20 - 0 ℃; for 1h;

DOI:10.1021/jo0349173

Reference yield: 41.0%

(-)-(4E)-(3S,SS)-4-(p-tolylsulfinyl)hepta-1,4,6-trien-3-ol (219776-31-5) → (+)-(2R,3R,4R,5S,SS)-3,4-epoxy-4-(p-tolylsulfinyl)-5-vinyl-tetrahydrofuran-2-methanol (219776-33-7) + (2R,3R,4R,5S)-3,4-epoxy-2-(p-tolylsulfonyl)-5-vinyl-tetrahydrofuran-2-methanol (219776-34-8) + 3,4-epoxy-2-(p-tolylsulfonyl)-5-vinyl-tetrahydrofuran-2-methanol

Guidance literature:

With tert.-butylhydroperoxide; potassium hydride; In tetrahydrofuran; at -20 - 0 ℃; for 0.666667h;

DOI:10.1021/jo0349173

Reference yield: 10.0%

(-)-(4E)-(3S,SS)-4-(p-tolylsulfinyl)hepta-1,4,6-trien-3-ol (219776-31-5) → (+)-(2R,3R,4R,5S,SS)-3,4-epoxy-4-(p-tolylsulfinyl)-5-vinyl-tetrahydrofuran-2-methanol (219776-33-7) + (2R,3R,4R,5S)-3,4-epoxy-2-(p-tolylsulfonyl)-5-vinyl-tetrahydrofuran-2-methanol (219776-34-8) + (+)-cis-4-(p-tolylsulfinyl)-5-vinyl-2,5-dihydrofuran-2-methanol (219776-32-6)

Guidance literature:

With tert.-butylhydroperoxide; potassium hydride; In tetrahydrofuran; at -78 - 4 ℃; for 18h;

DOI:10.1021/jo0349173

upstream raw materials:

(-)-(4E)-(3S,S_S)-4-(p-tolylsulfinyl)hepta-1,4,6-trien-3-ol

(+)-cis-4-(p-tolylsulfinyl)-5-vinyl-2,5-dihydrofuran-2-methanol

(R)-(1,3-Butadienyl)-p-tolyl-sulfoxid

(+)-(4E)-(3R,S_S)-4-(p-tolylsulfinyl)hepta-1,4,6-trien-3-ol

Downstream raw materials:

(2R,3R,4R,5S)-3,4-epoxy-2-(p-tolylsulfonyl)-5-vinyl-tetrahydrofuran-2-methanol

tert-Butyl-diphenyl-[(1R,2R,4S,5R)-5-((S)-toluene-4-sulfinyl)-4-vinyl-3,6-dioxa-bicyclo[3.1.0]hex-2-ylmethoxy]-silane

(+)-(2S,4S,5S)-2-(tert-butyldiphenylsilyloxymethyl)-5-vinyltetrahydrofuran-4-ol

(-)-(1S,5S,7S)-7-(tert-butyldiphenylsilyloxymethyl)-2,6-dioxabicyclo[3.3.0^4,8]octan-3-ol

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