(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

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-carbonyl chloride
• CAS No.: 133344-20-4
• Molecular Formula: C₁₇H₂₀ClNO₅S
• Molecular Weight: 385.869

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-carbonyl chloride

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-carbonyl chloride

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-carbonyl chloride

There total 4 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-carbonyl chloride 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: 100.0%

(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) → (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-carbonyl chloride (133344-20-4)

Guidance literature:

With thionyl chloride; for 0.25h; Heating;

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-carbonyl chloride (133344-20-4)

Guidance literature:

Multi-step reaction with 4 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

4: 100 percent / SOCl₂ / 0.25 h / Heating

With sodium hydroxide; thionyl chloride; 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-carbonyl chloride (133344-20-4)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: 100 percent / SOCl₂ / 0.25 h / Heating

With sodium hydroxide; thionyl chloride; 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

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

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

Downstream raw materials:

(+/-)-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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