2-(4-methoxy-benzyl)-3-[4-(4-methoxy-benzyloxy)-butyl]-6-vinyl-[1,2]oxazinane-4-carboxylic acid methyl ester

Base Information

• Chemical Name: 2-(4-methoxy-benzyl)-3-[4-(4-methoxy-benzyloxy)-butyl]-6-vinyl-[1,2]oxazinane-4-carboxylic acid methyl ester
• CAS No.: 916728-14-8
• Molecular Formula: C₂₈H₃₇NO₆
• Molecular Weight: 483.605
• Mol file: 916728-14-8.mol

Synonyms:2-(4-methoxy-benzyl)-3-[4-(4-methoxy-benzyloxy)-butyl]-6-vinyl-[1,2]oxazinane-4-carboxylic acid methyl ester

Chemical Property of 2-(4-methoxy-benzyl)-3-[4-(4-methoxy-benzyloxy)-butyl]-6-vinyl-[1,2]oxazinane-4-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(4-methoxy-benzyl)-3-[4-(4-methoxy-benzyloxy)-butyl]-6-vinyl-[1,2]oxazinane-4-carboxylic acid methyl ester

There total 1 articles about 2-(4-methoxy-benzyl)-3-[4-(4-methoxy-benzyloxy)-butyl]-6-vinyl-[1,2]oxazinane-4-carboxylic acid methyl ester 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:

(S)-2-vinylcyclopropane-1,1-dicarboxylic acid dimethyl ester (53376-55-9) + N-(4-methoxybenzyl)hydroxylamine (51307-59-6) + 5-((4-methoxybenzyl)oxy)pentanal (131375-69-4) → 2-(4-methoxy-benzyl)-3-[4-(4-methoxy-benzyloxy)-butyl]-6-vinyl-[1,2]oxazinane-4-carboxylic acid methyl ester (916728-14-8)

Guidance literature:

N-(4-methoxybenzyl)hydroxylamine; 5-((4-methoxybenzyl)oxy)pentanal; With 4 A molecular sieve; ytterbium(III) triflate; In toluene; at 20 ℃; for 0.5h;

(S)-2-vinylcyclopropane-1,1-dicarboxylic acid dimethyl ester; In toluene; Heating;

With dimethyl sulfoxide; lithium chloride; at 160 ℃; for 2h;

DOI:10.1002/anie.200602569

Reference yield: 80.0%

2-(4-methoxy-benzyl)-3-[4-(4-methoxy-benzyloxy)-butyl]-6-vinyl-[1,2]oxazinane-4-carboxylic acid methyl ester (916728-14-8) → 4-hydroxy-2-(4-methoxy-benzyl)-3-[4-(4-methoxy-benzyloxy)-butyl]-6-vinyl-[1,2]oxazinane-4-carboxylic acid methyl ester

Guidance literature:

With potassium hexamethylsilazane; 2-[(4-methylphenyl)sulfonyl]-3-phenyl-oxaziridine; In tetrahydrofuran; for 2.5h; cooling;

DOI:10.1002/anie.200602569

Reference yield:

2-(4-methoxy-benzyl)-3-[4-(4-methoxy-benzyloxy)-butyl]-6-vinyl-[1,2]oxazinane-4-carboxylic acid methyl ester (916728-14-8) → 5-hydroxy-3-(4-methoxy-benzyl)-4-[4-(4-methoxy-benzyloxy)-butyl]-2-oxa-3-aza-bicyclo[3.3.1]non-7-en-6-one (916728-20-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 80 percent / KHMDS; 3-phenyl-2-(p-toluenesulfonyl)-oxaziridine / tetrahydrofuran / 2.5 h / cooling

2: 97 percent / LiAlH₄ / diethyl ether; tetrahydrofuran / 2 h / cooling

3: p-toluenesulfonic acid / dimethylsulfoxide / 48 h / 20 °C

4: 93 percent / aq. HCl / tetrahydrofuran / 48 h

5: 64 percent / o-iodobenzoic acid; dimethyl sulfoxide / 2 h / 20 °C

6: 76 percent / tetrahydrofuran / 3 h

7: 79 percent / o-iodobenzoic acid; dimethyl sulfoxide / 2 h

8: 74 percent / Grubbs' 2-nd generation catalyst / CH₂Cl₂ / 2 h / Heating

With hydrogenchloride; lithium aluminium tetrahydride; 2-Iodobenzoic acid; potassium hexamethylsilazane; toluene-4-sulfonic acid; dimethyl sulfoxide; 2-[(4-methylphenyl)sulfonyl]-3-phenyl-oxaziridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide;

DOI:10.1002/anie.200602569

upstream raw materials:

(S)-2-vinylcyclopropane-1,1-dicarboxylic acid dimethyl ester

N-(4-methoxybenzyl)hydroxylamine

5-((4-methoxybenzyl)oxy)pentanal

Downstream raw materials:

5-hydroxy-3-(4-methoxy-benzyl)-4-[4-(4-methoxy-benzyloxy)-butyl]-2-oxa-3-aza-bicyclo[3.3.1]non-7-en-6-one

4-hydroxy-2-(4-methoxy-benzyl)-3-[4-(4-methoxy-benzyloxy)-butyl]-6-vinyl-[1,2]oxazinane-4-carbaldehyde

10-(4-methoxy-benzyl)-11-[4-(4-methoxy-benzyloxy)-butyl]-2,9-dioxa-10-aza-tricyclo[6.3.1.0^1,5]dodeca-4,6-dien-3-one

4-hydroxymethyl-2-(4-methoxy-benzyl)-3-[4-(4-methoxy-benzyloxy)-butyl]-6-vinyl-[1,2]oxazinan-4-ol