phenylmethyl (4S)-4-(2-methylpropyl)-6-oxo-1,3-oxazinane-3-carboxylate

Base Information

• Chemical Name: phenylmethyl (4S)-4-(2-methylpropyl)-6-oxo-1,3-oxazinane-3-carboxylate
• CAS No.: 922705-34-8
• Molecular Formula: C₁₆H₂₁NO₄
• Molecular Weight: 291.347
• Mol file: 922705-34-8.mol

Synonyms:phenylmethyl (4S)-4-(2-methylpropyl)-6-oxo-1,3-oxazinane-3-carboxylate

Chemical Property of phenylmethyl (4S)-4-(2-methylpropyl)-6-oxo-1,3-oxazinane-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenylmethyl (4S)-4-(2-methylpropyl)-6-oxo-1,3-oxazinane-3-carboxylate

There total 3 articles about phenylmethyl (4S)-4-(2-methylpropyl)-6-oxo-1,3-oxazinane-3-carboxylate 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: 68.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + N-Benzyloxycarbonyl-L-Homoleucine (118247-68-0) → phenylmethyl (4S)-4-(2-methylpropyl)-6-oxo-1,3-oxazinane-3-carboxylate (922705-34-8)

Guidance literature:

With 4 A molecular sieve; camphor-10-sulfonic acid; In toluene; at 90 ℃; for 4h;

DOI:10.1021/jo0700326

Reference yield:

Z-Leu-OH (2018-66-8) → phenylmethyl (4S)-4-(2-methylpropyl)-6-oxo-1,3-oxazinane-3-carboxylate (922705-34-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: ClCOOEt; N-methylmorpholine / tetrahydrofuran / 0.25 h / -15 °C

1.2: tetrahydrofuran; CH₂Cl₂ / -15 - 20 °C

2.1: CF₃COOAg / dioxane; H₂O / 0.5 h / sonication

3.1: 31 percent / CSA; AcOH / toluene / 90 °C

With 4-methyl-morpholine; chloroformic acid ethyl ester; camphor-10-sulfonic acid; silver trifluoroacetate; acetic acid; In tetrahydrofuran; 1,4-dioxane; water; toluene; 2.1: Wolff rearrangement;

DOI:10.1002/hlca.200690235

Reference yield:

(3-diazo-1-(S)-(2-methylpropyl)-2-oxopropyl)carbamic acid benzyl ester (102123-81-9) → phenylmethyl (4S)-4-(2-methylpropyl)-6-oxo-1,3-oxazinane-3-carboxylate (922705-34-8)

Guidance literature:

Multi-step reaction with 2 steps

1: CF₃COOAg / dioxane; H₂O / 0.5 h / sonication

2: 31 percent / CSA; AcOH / toluene / 90 °C

camphor-10-sulfonic acid; silver trifluoroacetate; acetic acid; In 1,4-dioxane; water; toluene; 1: Wolff rearrangement;

DOI:10.1002/hlca.200690235

upstream raw materials:

formaldehyd

N-Benzyloxycarbonyl-L-Homoleucine

Z-Leu-OH

(3-diazo-1-(S)-(2-methylpropyl)-2-oxopropyl)carbamic acid benzyl ester

Downstream raw materials:

(4S,5S)-N-benzyloxycarbonyl-5-hydroxy-4-isobutyl-1,3-oxazinan-6-one

(4S,5R)-N-benzyloxycarbonyl-4-isobutyl-5-methyl-1,3-oxazinan-6-one

(2S,3S)-3-Benzyloxycarbonylamino-2-hydroxy-5-methyl-hexanoic acid

(4S,5R)-N-benzyloxycarbonyl-5-(4-nitrobenzoyloxy)-4-(2-methylpropyl)-1,3-oxazinan-6-one