(3S,4R,5S)-methyl 4-(benzyloxycarbonylamino)-5-((R)-1,4-dioxaspiro[4.5]decan-2-yl)tetrahydrofuran-3-carboxylate

Base Information

Chemical Name:(3S,4R,5S)-methyl 4-(benzyloxycarbonylamino)-5-((R)-1,4-dioxaspiro[4.5]decan-2-yl)tetrahydrofuran-3-carboxylate
CAS No.:1393571-25-9
Molecular Formula:C₂₂H₂₉NO₇
Molecular Weight:419.475
Hs Code.:

Synonyms:(3S,4R,5S)-methyl 4-(benzyloxycarbonylamino)-5-((R)-1,4-dioxaspiro[4.5]decan-2-yl)tetrahydrofuran-3-carboxylate

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Chemical Property of (3S,4R,5S)-methyl 4-(benzyloxycarbonylamino)-5-((R)-1,4-dioxaspiro[4.5]decan-2-yl)tetrahydrofuran-3-carboxylate

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Technology Process of (3S,4R,5S)-methyl 4-(benzyloxycarbonylamino)-5-((R)-1,4-dioxaspiro[4.5]decan-2-yl)tetrahydrofuran-3-carboxylate

There total 6 articles about (3S,4R,5S)-methyl 4-(benzyloxycarbonylamino)-5-((R)-1,4-dioxaspiro[4.5]decan-2-yl)tetrahydrofuran-3-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:

: 186581-53-3,908094-01-9,334-88-3
diazomethane

: C₂₁H₂₇NO₇

: 1393571-25-9
(3S,4R,5S)-methyl 4-(benzyloxycarbonylamino)-5-((R)-1,4-dioxaspiro[4.5]decan-2-yl)tetrahydrofuran-3-carboxylate

Guidance literature:: In diethyl ether; at 0 ℃; for 0.25h;
DOI:10.1016/j.tetlet.2012.05.126

Reference yield:

: 1393571-19-1
2-nitro-1-((R)-1,4-dioxaspiro[4.5]decan-2-yl)ethanol

: 1393571-25-9
(3S,4R,5S)-methyl 4-(benzyloxycarbonylamino)-5-((R)-1,4-dioxaspiro[4.5]decan-2-yl)tetrahydrofuran-3-carboxylate

Guidance literature:: Multi-step reaction with 7 steps

1.1: methanesulfonyl chloride; triethylamine / dichloromethane / 0.75 h / -30 °C

2.1: sodium hydride / dichloromethane / 1 h / 0 °C / Inert atmosphere

3.1: phenyl isocyanate; triethylamine / benzene / 72 h / 20 °C / Inert atmosphere

4.1: lithium aluminium tetrahydride / diethyl ether / 6.25 h / 0 - 20 °C

4.2: 0 °C

5.1: sodium hydrogencarbonate / water; ethyl acetate / 2 h / 20 °C

6.1: sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; potassium bromide / dichloromethane / 1 h / 0 °C / Brine

7.1: diethyl ether / 0.25 h / 0 °C

With sodium hypochlorite; lithium aluminium tetrahydride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrabutyl ammonium fluoride; sodium hydride; sodium hydrogencarbonate; phenyl isocyanate; methanesulfonyl chloride; triethylamine; potassium bromide; In diethyl ether; dichloromethane; water; ethyl acetate; benzene; 2.1: Michael addition;
DOI:10.1016/j.tetlet.2012.05.126

Reference yield:

: 1393571-23-7
(6S)-6-((R)-1,4-dioxaspiro[4.5]decan-2-yl)-3,3a,4,6-tetrahydrofuro[3,4-c]isoxazole

: 1393571-25-9
(3S,4R,5S)-methyl 4-(benzyloxycarbonylamino)-5-((R)-1,4-dioxaspiro[4.5]decan-2-yl)tetrahydrofuran-3-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: lithium aluminium tetrahydride / diethyl ether / 6.25 h / 0 - 20 °C

1.2: 0 °C

2.1: sodium hydrogencarbonate / water; ethyl acetate / 2 h / 20 °C

3.1: sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; potassium bromide / dichloromethane / 1 h / 0 °C / Brine

4.1: diethyl ether / 0.25 h / 0 °C

With sodium hypochlorite; lithium aluminium tetrahydride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; potassium bromide; In diethyl ether; dichloromethane; water; ethyl acetate;
DOI:10.1016/j.tetlet.2012.05.126