(1R,2R,6S,7R,9R)-4,4-Dimethyl-8-(toluene-4-sulfonyl)-3,5-dioxa-8-aza-tricyclo[5.2.1.0^2,6]decane-9-carboxylic acid

Base Information

• Chemical Name: (1R,2R,6S,7R,9R)-4,4-Dimethyl-8-(toluene-4-sulfonyl)-3,5-dioxa-8-aza-tricyclo[5.2.1.0^2,6]decane-9-carboxylic acid
• CAS No.: 133344-19-1
• Molecular Formula: C₁₇H₂₁NO₆S
• Molecular Weight: 367.423

Synonyms:(1R,2R,6S,7R,9R)-4,4-Dimethyl-8-(toluene-4-sulfonyl)-3,5-dioxa-8-aza-tricyclo[5.2.1.0^2,6]decane-9-carboxylic acid

Chemical Property of (1R,2R,6S,7R,9R)-4,4-Dimethyl-8-(toluene-4-sulfonyl)-3,5-dioxa-8-aza-tricyclo[5.2.1.0^2,6]decane-9-carboxylic acid

Chemical Property:

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Technology Process of (1R,2R,6S,7R,9R)-4,4-Dimethyl-8-(toluene-4-sulfonyl)-3,5-dioxa-8-aza-tricyclo[5.2.1.0^2,6]decane-9-carboxylic acid

There total 3 articles about (1R,2R,6S,7R,9R)-4,4-Dimethyl-8-(toluene-4-sulfonyl)-3,5-dioxa-8-aza-tricyclo[5.2.1.0^2,6]decane-9-carboxylic acid 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: 96.0%

(1R,2R,6S,7R,9R)-4,4-Dimethyl-8-(toluene-4-sulfonyl)-3,5-dioxa-8-aza-tricyclo[5.2.1.02,6]decane-9-carboxylic acid ethyl ester (133344-18-0) → (1R,2R,6S,7R,9R)-4,4-Dimethyl-8-(toluene-4-sulfonyl)-3,5-dioxa-8-aza-tricyclo[5.2.1.02,6]decane-9-carboxylic acid (133344-19-1)

Guidance literature:

With sodium hydroxide; In methanol; at 25 ℃;

DOI:10.1016/S0040-4039(00)97035-7

Reference yield:

(1S,3S,4R)-2-(Toluene-4-sulfonyl)-2-aza-bicyclo[2.2.1]hept-5-ene-3-carboxylic acid ethyl ester (133344-08-8) → (1R,2R,6S,7R,9R)-4,4-Dimethyl-8-(toluene-4-sulfonyl)-3,5-dioxa-8-aza-tricyclo[5.2.1.02,6]decane-9-carboxylic acid (133344-19-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / NMO / OsO₄ / acetone; tetrahydrofuran / 1 h / 25 °C

2: 98 percent / TsOH / acetone / 0.25 h / 25 °C

3: 96 percent / 10percent aq. NaOH / methanol / 25 °C

With sodium hydroxide; N-methyl-2-indolinone; osmium(VIII) oxide; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; acetone;

DOI:10.1016/S0040-4039(00)97035-7

Reference yield:

(1S,3S,4S,5S,6R)-5,6-Dihydroxy-2-(toluene-4-sulfonyl)-2-aza-bicyclo[2.2.1]heptane-3-carboxylic acid ethyl ester → (1R,2R,6S,7R,9R)-4,4-Dimethyl-8-(toluene-4-sulfonyl)-3,5-dioxa-8-aza-tricyclo[5.2.1.02,6]decane-9-carboxylic acid (133344-19-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / TsOH / acetone / 0.25 h / 25 °C

2: 96 percent / 10percent aq. NaOH / methanol / 25 °C

With sodium hydroxide; toluene-4-sulfonic acid; In methanol; acetone;

DOI:10.1016/S0040-4039(00)97035-7

upstream raw materials:

(1R,2R,6S,7R,9R)-4,4-Dimethyl-8-(toluene-4-sulfonyl)-3,5-dioxa-8-aza-tricyclo[5.2.1.0^2,6]decane-9-carboxylic acid ethyl ester

(1S,3S,4R)-2-(Toluene-4-sulfonyl)-2-aza-bicyclo[2.2.1]hept-5-ene-3-carboxylic acid ethyl ester

Downstream raw materials:

(1R,2R,6S,7R,9R)-4,4-Dimethyl-8-(toluene-4-sulfonyl)-3,5-dioxa-8-aza-tricyclo[5.2.1.0^2,6]decane-9-carbonyl chloride

(+/-)-1-(4-toluenesulfonyl)amino-4-hydroxymethyl-2,3-isopropylidenedioxycyclopentane

(1R,2R,6S,7R,9R)-9-Isocyanato-4,4-dimethyl-8-(toluene-4-sulfonyl)-3,5-dioxa-8-aza-tricyclo[5.2.1.0^2,6]decane

[(1R,2R,6S,7R,9R)-4,4-Dimethyl-8-(toluene-4-sulfonyl)-3,5-dioxa-8-aza-tricyclo[5.2.1.0^2,6]dec-9-yl]-carbamic acid benzyl ester

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