(1R,2R,6S,7R,8S)-4,4-Dimethyl-8-(toluene-4-sulfonyl)-3,5-dioxa-10-aza-tricyclo[5.2.1.0^2,6]decane-10-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (1R,2R,6S,7R,8S)-4,4-Dimethyl-8-(toluene-4-sulfonyl)-3,5-dioxa-10-aza-tricyclo[5.2.1.0^2,6]decane-10-carboxylic acid tert-butyl ester
• CAS No.: 205813-80-5
• Molecular Formula: C₂₁H₂₉NO₆S
• Molecular Weight: 423.53

Synonyms:(1R,2R,6S,7R,8S)-4,4-Dimethyl-8-(toluene-4-sulfonyl)-3,5-dioxa-10-aza-tricyclo[5.2.1.0^2,6]decane-10-carboxylic acid tert-butyl ester

Chemical Property of (1R,2R,6S,7R,8S)-4,4-Dimethyl-8-(toluene-4-sulfonyl)-3,5-dioxa-10-aza-tricyclo[5.2.1.0^2,6]decane-10-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

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• Pictogram(s):  
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Technology Process of (1R,2R,6S,7R,8S)-4,4-Dimethyl-8-(toluene-4-sulfonyl)-3,5-dioxa-10-aza-tricyclo[5.2.1.0^2,6]decane-10-carboxylic acid tert-butyl ester

There total 9 articles about (1R,2R,6S,7R,8S)-4,4-Dimethyl-8-(toluene-4-sulfonyl)-3,5-dioxa-10-aza-tricyclo[5.2.1.0^2,6]decane-10-carboxylic acid tert-butyl 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: 85.0%

(1R,2R,6S,7R)-4,4-Dimethyl-8-(toluene-4-sulfonyl)-3,5-dioxa-10-aza-tricyclo[5.2.1.02,6]dec-8-ene-10-carboxylic acid tert-butyl ester → (1R,2R,6S,7R,8R)-4,4-Dimethyl-8-(toluene-4-sulfonyl)-3,5-dioxa-10-aza-tricyclo[5.2.1.02,6]decane-10-carboxylic acid tert-butyl ester + (1R,2R,6S,7R,8S)-4,4-Dimethyl-8-(toluene-4-sulfonyl)-3,5-dioxa-10-aza-tricyclo[5.2.1.02,6]decane-10-carboxylic acid tert-butyl ester (205813-80-5)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃; for 2h;

DOI:10.1021/jo971907r

Reference yield:

N-tert-butyloxycarbonyl-pyrrole (5176-27-2) → (1R,2R,6S,7R,8S)-4,4-Dimethyl-8-(toluene-4-sulfonyl)-3,5-dioxa-10-aza-tricyclo[5.2.1.02,6]decane-10-carboxylic acid tert-butyl ester (205813-80-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 84 percent / 48 h / 80 - 85 °C

2: 48 percent / NaH / tetrahydrofuran / 2 h

3: 95 percent / NaBH₄ / tetrahydrofuran; methanol / 2 h / 70 °C

4: 95 percent / MeMgBr / toluene; tetrahydrofuran / 0.08 h / Ambient temperature

5: 89 percent / NMO, OsO₄, NaHCO₃ / tetrahydrofuran; 2-methyl-propan-2-ol; H₂O / 2.5 h / Ambient temperature

6: 97 percent / p-TsOH*H₂O / acetone / 0.5 h / Ambient temperature

7: 85 percent / NaBH₄ / methanol / 2 h / 0 °C

With sodium tetrahydroborate; osmium(VIII) oxide; N-methyl-2-indolinone; methylmagnesium bromide; sodium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; water; acetone; toluene; tert-butyl alcohol;

DOI:10.1021/jo971907r

Reference yield:

ethynyl p-tolyl sulfone (13894-21-8) → (1R,2R,6S,7R,8S)-4,4-Dimethyl-8-(toluene-4-sulfonyl)-3,5-dioxa-10-aza-tricyclo[5.2.1.02,6]decane-10-carboxylic acid tert-butyl ester (205813-80-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 84 percent / 48 h / 80 - 85 °C

2: 48 percent / NaH / tetrahydrofuran / 2 h

3: 95 percent / NaBH₄ / tetrahydrofuran; methanol / 2 h / 70 °C

4: 95 percent / MeMgBr / toluene; tetrahydrofuran / 0.08 h / Ambient temperature

5: 89 percent / NMO, OsO₄, NaHCO₃ / tetrahydrofuran; 2-methyl-propan-2-ol; H₂O / 2.5 h / Ambient temperature

6: 97 percent / p-TsOH*H₂O / acetone / 0.5 h / Ambient temperature

7: 85 percent / NaBH₄ / methanol / 2 h / 0 °C

With sodium tetrahydroborate; osmium(VIII) oxide; N-methyl-2-indolinone; methylmagnesium bromide; sodium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; water; acetone; toluene; tert-butyl alcohol;

DOI:10.1021/jo971907r

upstream raw materials:

N-tert-butyloxycarbonyl-pyrrole

ethynyl p-tolyl sulfone

7-tert-butoxycarbonyl-2-(p-tolylsulfonyl)-7-azabicyclo[2.2.1]hept-2,5-diene

(1R,4S,5S,6S)-5-((S)-2-Hydroxy-1-methyl-ethoxy)-6-(toluene-4-sulfonyl)-7-aza-bicyclo[2.2.1]hept-2-ene-7-carboxylic acid tert-butyl ester

Downstream raw materials:

[(3aR,4R,7aS)-2,2-Dimethyl-6-(toluene-4-sulfonyl)-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-4-yl]-carbamic acid tert-butyl ester

(-)-conduramine C₁

((1R,5S,6R)-5,6-Dihydroxy-cyclohex-3-enyl)-carbamic acid tert-butyl ester

((3aR,4R,6S,7S,7aS)-7-Hydroxy-2,2-dimethyl-6-phenylselanyl-hexahydro-benzo[1,3]dioxol-4-yl)-carbamic acid tert-butyl ester

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