[(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

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]dec-9-yl]-carbamic acid benzyl ester
• CAS No.: 133344-23-7
• Molecular Formula: C₂₄H₂₈N₂O₆S
• Molecular Weight: 472.562

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]dec-9-yl]-carbamic acid benzyl ester

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]dec-9-yl]-carbamic acid benzyl ester

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]dec-9-yl]-carbamic acid benzyl ester

There total 7 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]dec-9-yl]-carbamic acid benzyl 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: 76.0%

(1R,2R,6S,7R,9R)-9-Isocyanato-4,4-dimethyl-8-(toluene-4-sulfonyl)-3,5-dioxa-8-aza-tricyclo[5.2.1.02,6]decane (133344-22-6) + benzyl alcohol (100-51-6,185532-71-2) → [(1R,2R,6S,7R,9R)-4,4-Dimethyl-8-(toluene-4-sulfonyl)-3,5-dioxa-8-aza-tricyclo[5.2.1.02,6]dec-9-yl]-carbamic acid benzyl ester (133344-23-7)

Guidance literature:

In toluene; for 2h; 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]dec-9-yl]-carbamic acid benzyl ester (133344-23-7)

Guidance literature:

Multi-step reaction with 7 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

5: 89 percent / aq. NaN₃, tetramethyl ammonium bromide / CH₂Cl₂ / 25 °C

6: 100 percent / toluene / 0.5 h / Heating

7: 76 percent / toluene / 2 h / Heating

With sodium hydroxide; thionyl chloride; sodium azide; N-methyl-2-indolinone; tetramethylammonium bromide; osmium(VIII) oxide; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; acetone; toluene;

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]dec-9-yl]-carbamic acid benzyl ester (133344-23-7)

Guidance literature:

Multi-step reaction with 6 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

4: 89 percent / aq. NaN₃, tetramethyl ammonium bromide / CH₂Cl₂ / 25 °C

5: 100 percent / toluene / 0.5 h / Heating

6: 76 percent / toluene / 2 h / Heating

With sodium hydroxide; thionyl chloride; sodium azide; tetramethylammonium bromide; toluene-4-sulfonic acid; In methanol; dichloromethane; acetone; toluene;

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

upstream raw materials:

(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

benzyl alcohol

(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

Downstream raw materials:

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

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