ethyl (1R,3S,4R,5R)-4-acetamido-3-(tert-butoxycarbonylamino)-5-hydroxycyclohexanecarboxylate

Base Information

Chemical Name:ethyl (1R,3S,4R,5R)-4-acetamido-3-(tert-butoxycarbonylamino)-5-hydroxycyclohexanecarboxylate
CAS No.:1224161-53-8
Molecular Formula:C₁₆H₂₈N₂O₆
Molecular Weight:344.408
Hs Code.:

Synonyms:ethyl (1R,3S,4R,5R)-4-acetamido-3-(tert-butoxycarbonylamino)-5-hydroxycyclohexanecarboxylate

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Chemical Property of ethyl (1R,3S,4R,5R)-4-acetamido-3-(tert-butoxycarbonylamino)-5-hydroxycyclohexanecarboxylate

Chemical Property:

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Technology Process of ethyl (1R,3S,4R,5R)-4-acetamido-3-(tert-butoxycarbonylamino)-5-hydroxycyclohexanecarboxylate

There total 9 articles about ethyl (1R,3S,4R,5R)-4-acetamido-3-(tert-butoxycarbonylamino)-5-hydroxycyclohexanecarboxylate 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: 50.0%

: 24424-99-5
di-tert-butyl dicarbonate

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

: 1224161-53-8
ethyl (1R,3S,4R,5R)-4-acetamido-3-(tert-butoxycarbonylamino)-5-hydroxycyclohexanecarboxylate

: 1224161-52-7
(3aR,6S,7R,7aS)-7-acetylamino-6-tert-butoxycarbonylamino-2,2-dimethyl-3a,6,7,7a-tetrahydrobenzo[1,3]dioxole-4-carboxylic acid ethyl ester

Guidance literature:: In dichloromethane; at 20 ℃; Inert atmosphere;
DOI:10.1002/adsc.200900844

Reference yield: 50.0%

: 24424-99-5
di-tert-butyl dicarbonate

: 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

: 1224161-53-8
ethyl (1R,3S,4R,5R)-4-acetamido-3-(tert-butoxycarbonylamino)-5-hydroxycyclohexanecarboxylate

: 1224161-52-7
(3aR,6S,7R,7aS)-7-acetylamino-6-tert-butoxycarbonylamino-2,2-dimethyl-3a,6,7,7a-tetrahydrobenzo[1,3]dioxole-4-carboxylic acid ethyl ester

Guidance literature:: (3aR,7R,7aS)-ethyl-7-acetamido-6-(hydroxyimino)-2,2-dimethyl-3a,6,7,7a-tetrahydrobenzo[d][1,3]dioxole-4-carboxylate; With Rh/Al₂O₃; hydrogen; In ethanol; water; for 16h; under 3102.97 Torr;

di-tert-butyl dicarbonate; In dichloromethane; at 20 ℃; for 6h; Inert atmosphere;
DOI:10.1021/jo2018872

Reference yield:

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

: 1224161-53-8
ethyl (1R,3S,4R,5R)-4-acetamido-3-(tert-butoxycarbonylamino)-5-hydroxycyclohexanecarboxylate

: 1224161-52-7
(3aR,6S,7R,7aS)-7-acetylamino-6-tert-butoxycarbonylamino-2,2-dimethyl-3a,6,7,7a-tetrahydrobenzo[1,3]dioxole-4-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: toluene-4-sulfonic acid / 20 °C

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

3: molybdenum hexacarbonyl / acetonitrile; water / 3 h / 85 °C

4: acetic anhydride; chromium(VI) oxide / dichloromethane / 0.08 h / 4 °C

5: hydroxylamine hydrochloride; pyridine / dichloromethane; ethanol / 17 h / 20 °C / Cooling with ice

6: hydrogen / 5% rhodium on activated aluminium oxide / ethanol / 16 h / 3102.97 Torr

7: dichloromethane / 6 h / 20 °C

With pyridine; chromium(VI) oxide; sodium periodate; hydroxylamine hydrochloride; hydrogen; acetic anhydride; toluene-4-sulfonic acid; molybdenum hexacarbonyl; 5% rhodium on activated aluminium oxide; In methanol; ethanol; dichloromethane; water; acetonitrile;