(3R,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: (3R,4'S)-2-benzyl-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-4-methoxy-3,6-dihydro-2H-1,2-oxazine
• CAS No.: 227622-64-2
• Molecular Formula: C₁₇H₂₃NO₄
• Molecular Weight: 305.374
• Mol file: 227622-64-2.mol

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about (3R,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: 77.0%

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 + (3R,4'S)-2-benzyl-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-4-methoxy-3,6-dihydro-2H-1,2-oxazine (227622-64-2)

Guidance literature:

N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone; With diethylaluminium chloride; In diethyl ether; hexane; at 20 ℃; for 0.166667h;

1-methoxyallenyllithium; In diethyl ether; hexane; at -78 ℃; for 1h;

DOI:10.1002/ejoc.200400627

Reference yield:

Methoxyallene (13169-00-1) + N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone (91190-38-4,111058-38-9,1165677-00-8) → (3R,4'S)-2-benzyl-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-4-methoxy-3,6-dihydro-2H-1,2-oxazine (227622-64-2) + (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:

With n-butyllithium; diethylaluminium chloride; Yield given; Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1.) Et₂O, 2.) Et₂O, -78 deg C, 2 h;

DOI:10.1055/s-1999-2662

Reference yield:

Methoxyallene (13169-00-1) + 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 + (3R,4'S)-2-benzyl-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-4-methoxy-3,6-dihydro-2H-1,2-oxazine (227622-64-2) + (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:

With n-butyllithium; Yield given; Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1.) THF, hexane, -40 deg C, 5 min, 2.) THF, hexane, -78 deg C, 1.5 h;

DOI:10.1055/s-1999-2662

upstream raw materials:

Methoxyallene

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

1-methoxyallenyllithium

Downstream raw materials:

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

(4aR,7S,7aR)-1-benzyl-4a-methoxyhexahydro-1H-furano[3,2-c][1,2]oxazin-7-ol

(R)-[Benzyl-(2-hydroperoxy-2-methoxy-ethoxy)-amino]-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-acetic acid methyl ester

(5R,4'S)-4-benzyl-7,7-dibromo-5-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-6-methoxy-3-oxa-4-azabicyclo[4.1.0]heptane