(1S,2S,6S,7S,8R,9S)-4,4-Dimethyl-9-(pyridine-2-sulfonyl)-3,5,10-trioxa-tricyclo[5.2.1.0^2,6]decane-8-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

Base Information

• Chemical Name: (1S,2S,6S,7S,8R,9S)-4,4-Dimethyl-9-(pyridine-2-sulfonyl)-3,5,10-trioxa-tricyclo[5.2.1.0^2,6]decane-8-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester
• CAS No.: 110390-53-9
• Molecular Formula: C₂₅H₃₅NO₇S
• Molecular Weight: 493.621

Synonyms:

Chemical Property of (1S,2S,6S,7S,8R,9S)-4,4-Dimethyl-9-(pyridine-2-sulfonyl)-3,5,10-trioxa-tricyclo[5.2.1.0^2,6]decane-8-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,6S,7S,8R,9S)-4,4-Dimethyl-9-(pyridine-2-sulfonyl)-3,5,10-trioxa-tricyclo[5.2.1.0^2,6]decane-8-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

There total 4 articles about (1S,2S,6S,7S,8R,9S)-4,4-Dimethyl-9-(pyridine-2-sulfonyl)-3,5,10-trioxa-tricyclo[5.2.1.0^2,6]decane-8-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl 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,2R,3S,4S,5S,6R)-5,6-Dihydroxy-3-(pyridine-2-sulfonyl)-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester + acetone (67-64-1) → (1S,2S,6S,7S,8R,9S)-4,4-Dimethyl-9-(pyridine-2-sulfonyl)-3,5,10-trioxa-tricyclo[5.2.1.02,6]decane-8-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester (110390-53-9)

Guidance literature:

With toluene-4-sulfonic acid; In various solvent(s); at 70 ℃; for 6h; Yield given;

DOI:10.1248/cpb.35.433

Reference yield:

(1R,2R,3S,4S)-3-((S)-Pyridine-2-sulfinyl)-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester (121467-52-5) → (1S,2S,6S,7S,8R,9S)-4,4-Dimethyl-9-(pyridine-2-sulfonyl)-3,5,10-trioxa-tricyclo[5.2.1.02,6]decane-8-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester (110390-53-9)

Guidance literature:

Multi-step reaction with 3 steps

1: OsO₄/Me₃NO / 12 h / Ambient temperature

2: p-toluenesulfonic acid / various solvent(s) / 6 h / 70 °C

3: m-CPBA

With osmium(VIII) oxide; trimethylamine-N-oxide; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; In various solvent(s);

DOI:10.1248/cpb.35.433

Reference yield:

(1'R,2'S,5'R)-menthyl (1S,2R,3S,4S,5S,6S)-5,6-dihydroxy-3-<(S)S-2-pyridylsulphinyl>-7-oxabicyclo<2.2.1>heptane-2-carboxylate (136340-68-6) → (1S,2S,6S,7S,8R,9S)-4,4-Dimethyl-9-(pyridine-2-sulfonyl)-3,5,10-trioxa-tricyclo[5.2.1.02,6]decane-8-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester (110390-53-9)

Guidance literature:

Multi-step reaction with 2 steps

1: p-toluenesulfonic acid / various solvent(s) / 6 h / 70 °C

2: m-CPBA

With toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; In various solvent(s);

DOI:10.1248/cpb.35.433

upstream raw materials:

(1'R,2'S,5'R)-menthyl (1S,2R,3S,4S,5S,6S)-5,6-(isopropylidenedioxy)-3-<(S)_S-2-pyridylsulphinyl>-7-oxabicyclo<2.2.1>heptane

acetone

(1R,2R,3S,4S)-3-((S)-Pyridine-2-sulfinyl)-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

(1'R,2'S,5'R)-menthyl (1S,2R,3S,4S,5S,6S)-5,6-dihydroxy-3-<(S)_S-2-pyridylsulphinyl>-7-oxabicyclo<2.2.1>heptane-2-carboxylate

Downstream raw materials:

showdomycin

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