ethyl (3aR, 4R,6S,7R,7aS)-7-acetamido-6-amino-2,2-dimethylhexahydrobenzo[d][1,3]dioxole-4-carboxylate

Base Information

Chemical Name:ethyl (3aR, 4R,6S,7R,7aS)-7-acetamido-6-amino-2,2-dimethylhexahydrobenzo[d][1,3]dioxole-4-carboxylate
CAS No.:1224161-51-6
Molecular Formula:C₁₄H₂₄N₂O₅
Molecular Weight:300.355
Hs Code.:

Synonyms:ethyl (3aR, 4R,6S,7R,7aS)-7-acetamido-6-amino-2,2-dimethylhexahydrobenzo[d][1,3]dioxole-4-carboxylate

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Chemical Property of ethyl (3aR, 4R,6S,7R,7aS)-7-acetamido-6-amino-2,2-dimethylhexahydrobenzo[d][1,3]dioxole-4-carboxylate

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Technology Process of ethyl (3aR, 4R,6S,7R,7aS)-7-acetamido-6-amino-2,2-dimethylhexahydrobenzo[d][1,3]dioxole-4-carboxylate

There total 6 articles about ethyl (3aR, 4R,6S,7R,7aS)-7-acetamido-6-amino-2,2-dimethylhexahydrobenzo[d][1,3]dioxole-4-carboxylate 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:

: 1224161-50-5
(3aR,7R,7aS)-ethyl-7-acetamido-6-(hydroxyimino)-2,2-dimethyl-3a,6,7,7a-tetrahydrobenzo[d][1,3]dioxole-4-carboxylate

: 1349901-44-5
(1R,3S,4R,5R)-ethyl 4-acetamido-3-amino-5-hydroxycyclohexanecarboxylate

: 1224161-51-6
ethyl (3aR, 4R,6S,7R,7aS)-7-acetamido-6-amino-2,2-dimethylhexahydrobenzo[d][1,3]dioxole-4-carboxylate

Guidance literature:: With Rh/Al₂O₃; hydrogen; In ethanol; for 16h;
DOI:10.1002/adsc.200900844

Reference yield:

: 1173701-24-0
ethyl (3aS,4S,7R,7aS)-7-(acetylamino)-4-hydroxy-2,2-dimethyl-3a,4,7,7a-tetrahydro-1,3-benzodioxole-4-carboxylate

: 1349901-44-5
(1R,3S,4R,5R)-ethyl 4-acetamido-3-amino-5-hydroxycyclohexanecarboxylate

: 1224161-51-6
ethyl (3aR, 4R,6S,7R,7aS)-7-acetamido-6-amino-2,2-dimethylhexahydrobenzo[d][1,3]dioxole-4-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: chromium(VI) oxide / acetic anhydride / 0.08 h / 4 °C / Inert atmosphere

2: hydroxylamine hydrochloride / pyridine; ethanol; dichloromethane / 0 - 20 °C / Inert atmosphere

3: Rh/Al₂O₃; hydrogen / ethanol; water / 16 h / 3102.97 Torr

With chromium(VI) oxide; Rh/Al₂O₃; hydroxylamine hydrochloride; hydrogen; In pyridine; ethanol; dichloromethane; water; acetic anhydride;
DOI:10.1021/jo2018872

Reference yield:

: 1173701-22-8
(+)-ethyl (5S,6R)-5,6-dihydroxycyclohexa-1,3-dienecarboxylate

: 1349901-44-5
(1R,3S,4R,5R)-ethyl 4-acetamido-3-amino-5-hydroxycyclohexanecarboxylate

: 1224161-51-6
ethyl (3aR, 4R,6S,7R,7aS)-7-acetamido-6-amino-2,2-dimethylhexahydrobenzo[d][1,3]dioxole-4-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1: toluene-4-sulfonic acid / acetone / 20 °C / Inert atmosphere

2: sodium periodate / methanol / 16 h / 20 °C / Inert atmosphere

3: water; molybdenum hexacarbonyl / acetonitrile / 3 h / 80 °C

4: chromium(VI) oxide / acetic anhydride / 0.08 h / 4 °C / Inert atmosphere

5: hydroxylamine hydrochloride / pyridine; ethanol; dichloromethane / 0 - 20 °C / Inert atmosphere

6: Rh/Al₂O₃; hydrogen / ethanol; water / 16 h / 3102.97 Torr

With chromium(VI) oxide; sodium periodate; Rh/Al₂O₃; hydroxylamine hydrochloride; water; hydrogen; toluene-4-sulfonic acid; molybdenum hexacarbonyl; In pyridine; methanol; ethanol; dichloromethane; water; acetic anhydride; acetone; acetonitrile; 2: hetero-Diels-Alder cycloaddition;
DOI:10.1021/jo2018872