(3R,4'S,5'R,4''R)-2-benzyl-3-(2',2',2'',2''-tetramethyl-[4',4'']bi[[1,3]dioxolanyl]-5'-yl)-4-methoxy-3,6-dihydro-2H-1,2-oxazine

Base Information

• Chemical Name: (3R,4'S,5'R,4''R)-2-benzyl-3-(2',2',2'',2''-tetramethyl-[4',4'']bi[[1,3]dioxolanyl]-5'-yl)-4-methoxy-3,6-dihydro-2H-1,2-oxazine
• CAS No.: 851959-99-4
• Molecular Formula: C₂₂H₃₁NO₆
• Molecular Weight: 405.491
• Mol file: 851959-99-4.mol

Synonyms:(3R,4'S,5'R,4''R)-2-benzyl-3-(2',2',2'',2''-tetramethyl-[4',4'']bi[[1,3]dioxolanyl]-5'-yl)-4-methoxy-3,6-dihydro-2H-1,2-oxazine

Chemical Property of (3R,4'S,5'R,4''R)-2-benzyl-3-(2',2',2'',2''-tetramethyl-[4',4'']bi[[1,3]dioxolanyl]-5'-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,5'R,4''R)-2-benzyl-3-(2',2',2'',2''-tetramethyl-[4',4'']bi[[1,3]dioxolanyl]-5'-yl)-4-methoxy-3,6-dihydro-2H-1,2-oxazine

There total 2 articles about (3R,4'S,5'R,4''R)-2-benzyl-3-(2',2',2'',2''-tetramethyl-[4',4'']bi[[1,3]dioxolanyl]-5'-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: 89.0%

Methoxyallene (13169-00-1) + C18H25NO5 (1104460-72-1,143539-91-7) → (3R,4'S,5'R,4''R)-2-benzyl-3-(2',2',2'',2''-tetramethyl-[4',4'']bi[[1,3]dioxolanyl]-5'-yl)-4-methoxy-3,6-dihydro-2H-1,2-oxazine (851959-99-4)

Guidance literature:

Methoxyallene; With n-butyllithium; In diethyl ether; hexane; at -40 ℃; for 0.25h; Inert atmosphere;

C₁₈H₂₅NO₅; With diethylaluminium chloride; In diethyl ether; hexane; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1021/ol802514m

Reference yield: 70.0%

1-methoxyallenyllithium (61186-66-1) + (Z)-N-(1-deoxy-2,3:4,5-di-O-isopropylidene-D-mannito-1-ylidene)benzylamine N-oxide (143539-91-7) → (3S,4'S,5'R,4''R)-2-benzyl-3-(2',2',2'',2''-tetramethyl-[4',4'']bi[[1,3]dioxolanyl]-5'-yl)-4-methoxy-3,6-dihydro-2H-1,2-oxazine + (3R,4'S,5'R,4''R)-2-benzyl-3-(2',2',2'',2''-tetramethyl-[4',4'']bi[[1,3]dioxolanyl]-5'-yl)-4-methoxy-3,6-dihydro-2H-1,2-oxazine (851959-99-4)

Guidance literature:

(Z)-N-(1-deoxy-2,3:4,5-di-O-isopropylidene-D-mannito-1-ylidene)benzylamine N-oxide; With diethylaluminium chloride; In diethyl ether; hexane; at 20 ℃; for 0.166667h;

1-methoxyallenyllithium; In diethyl ether; hexane; at -78 ℃; for 2h;

DOI:10.1002/ejoc.200400627

Reference yield: 88.0%

(3R,4'S,5'R,4''R)-2-benzyl-3-(2',2',2'',2''-tetramethyl-[4',4'']bi[[1,3]dioxolanyl]-5'-yl)-4-methoxy-3,6-dihydro-2H-1,2-oxazine (851959-99-4) → C16H23NO6 (1122571-95-2)

Guidance literature:

With indium(III) chloride; water; In acetonitrile; at 20 ℃; for 3h; chemoselective reaction;

DOI:10.1055/s-0028-1083628

upstream raw materials:

1-methoxyallenyllithium

(Z)-N-(1-deoxy-2,3:4,5-di-O-isopropylidene-D-mannito-1-ylidene)benzylamine N-oxide

Methoxyallene

C₁₈H₂₅NO₅

Downstream raw materials:

(4aS,6R,7S,8R,8aS)-1-benzyl-6-(hydroxymethyl)-4a-methoxyhexahydro-1H,3H-pyrano[3,2-c][1,2]oxazine-7,8-diol

(4aS,6R,7S,8R,8aS)-1-benzyl-4a-methoxy-6-[(1-methoxy-1-methylethoxy)methyl]hexahydro-1H,3H-pyrano[3,2-c][1,2]oxazine-7,8-diol

C₁₆H₂₃NO₆

C₂₂H₃₃NO₇