ethyl (2S,3R,4R,5R)-4-(benzyloxy)-2,3-isopropylidenedioxy-1,6-dioxa-7-azaspiro[4.5]dec-7-ene-8-carboxylate

Base Information

Chemical Name:ethyl (2S,3R,4R,5R)-4-(benzyloxy)-2,3-isopropylidenedioxy-1,6-dioxa-7-azaspiro[4.5]dec-7-ene-8-carboxylate
CAS No.:496808-11-8
Molecular Formula:C₂₀H₂₅NO₇
Molecular Weight:391.421
Hs Code.:

Synonyms:ethyl (2S,3R,4R,5R)-4-(benzyloxy)-2,3-isopropylidenedioxy-1,6-dioxa-7-azaspiro[4.5]dec-7-ene-8-carboxylate

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Chemical Property of ethyl (2S,3R,4R,5R)-4-(benzyloxy)-2,3-isopropylidenedioxy-1,6-dioxa-7-azaspiro[4.5]dec-7-ene-8-carboxylate

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Technology Process of ethyl (2S,3R,4R,5R)-4-(benzyloxy)-2,3-isopropylidenedioxy-1,6-dioxa-7-azaspiro[4.5]dec-7-ene-8-carboxylate

There total 3 articles about ethyl (2S,3R,4R,5R)-4-(benzyloxy)-2,3-isopropylidenedioxy-1,6-dioxa-7-azaspiro[4.5]dec-7-ene-8-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: 62.0%

: 176098-48-9
(3aR,4R,6aR)-4-(benzyloxy)-2,2-dimethyl-5-methylenetetrahydrofuro[2,3-d][1,3]dioxole

ethyl 3-bromo-2-(hydroxyimino)propanoate: 73472-94-3
ethyl 3-bromo-2-(hydroxyimino)propanoate

: 496808-11-8
ethyl (2S,3R,4R,5R)-4-(benzyloxy)-2,3-isopropylidenedioxy-1,6-dioxa-7-azaspiro[4.5]dec-7-ene-8-carboxylate

Guidance literature:: With sodium carbonate; In dichloromethane; at 20 ℃; for 72h;
DOI:10.1016/S0040-4020(02)01251-6

Reference yield:

: 29580-99-2
(3aR,4S,5R,6aR)-4-(benzyloxy)-5-(iodomethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

: 496808-11-8
ethyl (2S,3R,4R,5R)-4-(benzyloxy)-2,3-isopropylidenedioxy-1,6-dioxa-7-azaspiro[4.5]dec-7-ene-8-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: 87 percent / DBU; molecular sieves 3 Angstroem / dimethylsulfoxide / 3 h / Heating

2: 62 percent / Na₂CO₃ / CH₂Cl₂ / 72 h / 20 °C

With 3 A molecular sieve; sodium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; dimethyl sulfoxide; 2: hetero-Diels-Alder addition;
DOI:10.1016/S0040-4020(02)01251-6

Reference yield:

: 34370-91-7,59358-33-7,68354-70-1,70798-12-8,19139-80-1
3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose

: 496808-11-8
ethyl (2S,3R,4R,5R)-4-(benzyloxy)-2,3-isopropylidenedioxy-1,6-dioxa-7-azaspiro[4.5]dec-7-ene-8-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: 89 percent / I₂; PPh₃; imidazole / toluene / 2 h / Heating

2: 87 percent / DBU; molecular sieves 3 Angstroem / dimethylsulfoxide / 3 h / Heating

3: 62 percent / Na₂CO₃ / CH₂Cl₂ / 72 h / 20 °C

With 1H-imidazole; 3 A molecular sieve; iodine; sodium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; In dichloromethane; dimethyl sulfoxide; toluene; 3: hetero-Diels-Alder addition;
DOI:10.1016/S0040-4020(02)01251-6