(3R,4R,4aR,5R,6S)-3-benzyloxy-5,6-isopropylidenedioxy-4-methoxyhexahydropyrrolo[1,2-b][1,2]oxazine

Base Information

Chemical Name:(3R,4R,4aR,5R,6S)-3-benzyloxy-5,6-isopropylidenedioxy-4-methoxyhexahydropyrrolo[1,2-b][1,2]oxazine
CAS No.:1608130-44-4
Molecular Formula:C₁₈H₂₅NO₅
Molecular Weight:335.4
Hs Code.:

Synonyms:(3R,4R,4aR,5R,6S)-3-benzyloxy-5,6-isopropylidenedioxy-4-methoxyhexahydropyrrolo[1,2-b][1,2]oxazine

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (3R,4R,4aR,5R,6S)-3-benzyloxy-5,6-isopropylidenedioxy-4-methoxyhexahydropyrrolo[1,2-b][1,2]oxazine

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Technology Process of (3R,4R,4aR,5R,6S)-3-benzyloxy-5,6-isopropylidenedioxy-4-methoxyhexahydropyrrolo[1,2-b][1,2]oxazine

There total 4 articles about (3R,4R,4aR,5R,6S)-3-benzyloxy-5,6-isopropylidenedioxy-4-methoxyhexahydropyrrolo[1,2-b][1,2]oxazine 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: 81.0%

: 1608130-36-4
(3R,4R,4aR,5R,6S)-5,6-isopropylidenedioxy-4-methoxyhexahydropyrrolo[1,2-b][1,2]oxazin-3-ol

: 100-39-0
benzyl bromide

: 1608130-44-4
(3R,4R,4aR,5R,6S)-3-benzyloxy-5,6-isopropylidenedioxy-4-methoxyhexahydropyrrolo[1,2-b][1,2]oxazine

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃; Inert atmosphere;
DOI:10.1002/ejoc.201301406 DOI:10.1002/ejoc.201301406

Reference yield:

: 1449739-97-2
(4aS,5R,6S)-5,6-isopropylidenedioxy-4-methoxy-4a,5,6,7-tetrahydro-2H-pyrrolo[1,2-b][1,2]oxazine

: 1608130-44-4
(3R,4R,4aR,5R,6S)-3-benzyloxy-5,6-isopropylidenedioxy-4-methoxyhexahydropyrrolo[1,2-b][1,2]oxazine

Guidance literature:: Multi-step reaction with 2 steps

1.1: borane-THF / tetrahydrofuran / 3 h / -30 - 20 °C / Inert atmosphere

1.2: -10 - 20 °C / Inert atmosphere

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C / Inert atmosphere

With borane-THF; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil;
DOI:10.1002/ejoc.201301406

Reference yield:

: 213598-50-6
(3S,4R)-3,4-O-isopropylidenedioxy-1-pyrroline-N-oxide

: 1608130-44-4
(3R,4R,4aR,5R,6S)-3-benzyloxy-5,6-isopropylidenedioxy-4-methoxyhexahydropyrrolo[1,2-b][1,2]oxazine

Guidance literature:: Multi-step reaction with 4 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.08 h / -40 °C / Inert atmosphere

1.2: 2 h / -78 °C / Inert atmosphere

2.1: magnesium sulfate / diethyl ether / 36 h / 20 °C / Inert atmosphere

3.1: borane-THF / tetrahydrofuran / 3 h / -30 - 20 °C / Inert atmosphere

3.2: -10 - 20 °C / Inert atmosphere

4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C / Inert atmosphere

With n-butyllithium; borane-THF; sodium hydride; magnesium sulfate; In tetrahydrofuran; diethyl ether; hexane; N,N-dimethyl-formamide; mineral oil;
DOI:10.1002/ejoc.201301406