(3S,4′S)-2-benzyl-3-(2′,2′-dimethyl-1′,3′-dioxolan-4′-yl)-4-methoxy-3,6-dihydro-2H-1,2-oxazine

Base Information

• Chemical Name: (3S,4′S)-2-benzyl-3-(2′,2′-dimethyl-1′,3′-dioxolan-4′-yl)-4-methoxy-3,6-dihydro-2H-1,2-oxazine
• CAS No.: 227622-58-4
• Molecular Formula: C₁₇H₂₃NO₄
• Molecular Weight: 305.374

Synonyms:(3S,4′S)-2-benzyl-3-(2′,2′-dimethyl-1′,3′-dioxolan-4′-yl)-4-methoxy-3,6-dihydro-2H-1,2-oxazine

Chemical Property of (3S,4′S)-2-benzyl-3-(2′,2′-dimethyl-1′,3′-dioxolan-4′-yl)-4-methoxy-3,6-dihydro-2H-1,2-oxazine

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Technology Process of (3S,4′S)-2-benzyl-3-(2′,2′-dimethyl-1′,3′-dioxolan-4′-yl)-4-methoxy-3,6-dihydro-2H-1,2-oxazine

There total 9 articles about (3S,4′S)-2-benzyl-3-(2′,2′-dimethyl-1′,3′-dioxolan-4′-yl)-4-methoxy-3,6-dihydro-2H-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%

1-methoxyallenyllithium (61186-66-1) + N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone (91190-38-4,111058-38-9,1165677-00-8) → (3S,4′S)-2-benzyl-3-(2′,2′-dimethyl-1′,3′-dioxolan-4′-yl)-4-methoxy-3,6-dihydro-2H-1,2-oxazine (227622-58-4)

Guidance literature:

In tetrahydrofuran; at -78 ℃; for 1h;

DOI:10.1021/ol0260573

Reference yield: 81.0%

1-methoxyallenyllithium (61186-66-1) + N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone (91190-38-4,111058-38-9,1165677-00-8) → (Z)-(4S)-4-(2'-methoxy-1',3'-butadienyl)-2,2-dimethyl-1,3-dioxolane + (E)-(4S)-4-(2'-methoxy-1',3'-butadienyl)-2,2-dimethyl-1,3-dioxolane + (3S,4′S)-2-benzyl-3-(2′,2′-dimethyl-1′,3′-dioxolan-4′-yl)-4-methoxy-3,6-dihydro-2H-1,2-oxazine (227622-58-4)

Guidance literature:

In tetrahydrofuran; hexane; at -78 ℃; for 1h;

DOI:10.1002/ejoc.200400627

Reference yield: 81.0%

1-methoxyallenyllithium (61186-66-1) + N-benzyl-1,2-O-isopropylidene-D-glyceraldehyde nitrone (91190-38-4,111058-38-9,1165677-00-8) → (3S,4′S)-2-benzyl-3-(2′,2′-dimethyl-1′,3′-dioxolan-4′-yl)-4-methoxy-3,6-dihydro-2H-1,2-oxazine (227622-58-4)

Guidance literature:

In tetrahydrofuran; at -78 ℃; for 2h; Inert atmosphere;

DOI:10.1002/chem.201001060

upstream raw materials:

Methoxyallene

N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone

1-methoxyallenyllithium

N-benzyl-1,2-O-isopropylidene-D-glyceraldehyde nitrone

Downstream raw materials:

(E)-(4R,4'R,5'S)-4-benzylamino-4-(5'-tert-butyldimethylsiloxymethyl-2',2'-dimethyl-1',3--dioxolan-4'-yl)-3-methoxybut-2-en-1-ol

(2aR,4aR,7aS,7bS)-7-benzyl-7b-methoxy-4,4-dimethylhexahydro-2H,4H-1,3,6-trioxa-7-azacyclopenta[cd]indene

(3S,4'S)-2-benzyl-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-3,4,5,6-tetrahydro-2H-1,2-oxazin-4-one

(3R,4S)-2-Benzyl-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-[1,2]oxazinan-4-ol

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