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

Base Information

Chemical Name:ethyl (2S,3R,4R,5R,8R)-4-(benzyloxy)-2,3-isopropylidenedioxy-1,6-dioxa-7-azaspiro[4.5]decane-8-carboxylate
CAS No.:496808-12-9
Molecular Formula:C₂₀H₂₇NO₇
Molecular Weight:393.437
Hs Code.:

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

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

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

There total 4 articles about ethyl (2S,3R,4R,5R,8R)-4-(benzyloxy)-2,3-isopropylidenedioxy-1,6-dioxa-7-azaspiro[4.5]decane-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: 60.0%

: 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

: 496808-12-9
ethyl (2S,3R,4R,5R,8R)-4-(benzyloxy)-2,3-isopropylidenedioxy-1,6-dioxa-7-azaspiro[4.5]decane-8-carboxylate

Guidance literature:: With sodium cyanoborohydride; acetic acid; at 20 ℃; for 24h;
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

: 496808-12-9
ethyl (2S,3R,4R,5R,8R)-4-(benzyloxy)-2,3-isopropylidenedioxy-1,6-dioxa-7-azaspiro[4.5]decane-8-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

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

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

3: 60 percent / NaCNBH₃; glacial acetic acid / 24 h / 20 °C

With 3 A molecular sieve; sodium cyanoborohydride; sodium carbonate; acetic acid; 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:

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

: 496808-12-9
ethyl (2S,3R,4R,5R,8R)-4-(benzyloxy)-2,3-isopropylidenedioxy-1,6-dioxa-7-azaspiro[4.5]decane-8-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: 62 percent / Na₂CO₃ / CH₂Cl₂ / 72 h / 20 °C

2: 60 percent / NaCNBH₃; glacial acetic acid / 24 h / 20 °C

With sodium cyanoborohydride; sodium carbonate; acetic acid; In dichloromethane; 1: hetero-Diels-Alder addition;
DOI:10.1016/S0040-4020(02)01251-6