(3S,5S,6R)-3-(3-Butenyl)-2-oxo-5,6-diphenyl-4-Morpholinecarboxylic Acid tert-Butyl Ester

Base Information

• Chemical Name: (3S,5S,6R)-3-(3-Butenyl)-2-oxo-5,6-diphenyl-4-Morpholinecarboxylic Acid tert-Butyl Ester
• CAS No.: 144542-72-3
• Molecular Formula: C₂₅H₂₉NO₄
• Molecular Weight: 407.51
• Mol file: 144542-72-3.mol

Synonyms:(3S,5S,6R)-4-(tert-butyloxycarbonyl)-5,6-diphenyl-3-(3'-butenyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

Chemical Property of (3S,5S,6R)-3-(3-Butenyl)-2-oxo-5,6-diphenyl-4-Morpholinecarboxylic Acid tert-Butyl Ester

Chemical Property:

• Solubility.: Dichloromethane

Purity/Quality:

(3S,5S,6R)-3-(3-Butenyl)-2-oxo-5,6-diphenyl-4-morpholinecarboxylicAcidtert-ButylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (3S,5S,6R)-3-(3-Butenyl)-2-oxo-5,6-diphenyl-4-morpholinecarboxylic Acid tert-Butyl Ester is a reactant used in the preparation of collagen cross-link pyridinolines.

Technology Process of (3S,5S,6R)-3-(3-Butenyl)-2-oxo-5,6-diphenyl-4-Morpholinecarboxylic Acid tert-Butyl Ester

There total 1 articles about (3S,5S,6R)-3-(3-Butenyl)-2-oxo-5,6-diphenyl-4-Morpholinecarboxylic Acid tert-Butyl 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: 89.0%

4-iodobut-1-ene (7766-51-0) + tert-butyl (2R,3S)-6-oxo-2,3-diphenylmorpholine-4-carboxylate (112741-49-8,173397-90-5) → (3S,5S,6R)-4-(tert-butyloxycarbonyl)-5,6-diphenyl-3-(3'-butenyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one (144542-72-3)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hexamethyldisilazane; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1016/0040-4020(95)00976-0

Reference yield: 88.7%

(3S,5S,6R)-4-(tert-butyloxycarbonyl)-5,6-diphenyl-3-(3'-butenyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one (144542-72-3) → tert-butyl (3S,5S,6R)-3-(2-((RS)oxiran-2-yl)ethyl)-2-oxo-5,6-diphenylmorpholine-4-carboxylate (937183-38-5)

Guidance literature:

With phosphate buffer; 3-chloro-benzenecarboperoxoic acid; In 1,2-dichloro-ethane; at 20 ℃; for 12h; pH=7;

DOI:10.1016/j.tetasy.2004.06.004

Reference yield:

(3S,5S,6R)-4-(tert-butyloxycarbonyl)-5,6-diphenyl-3-(3'-butenyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one (144542-72-3) → (2S,5R)-5-hydroxylysine monohydrochloride (93923-90-1,2219-28-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 88.7 percent / mCPBA; phosphate buffer / 1,2-dichloro-ethane / 12 h / 20 °C / pH 7

2.1: 47 percent / AcOH; NaI / tetrahydrofuran / 1 h / 20 °C

3.1: 81 percent / NaN₃ / dimethylformamide / 12 h / 20 °C

4.1: CF₃COOH / H₂O / 1 h / 20 °C

4.2: 88 percent / HCl; H₂ / Pd/C / methanol; H₂O / 24 h / 25 °C

With sodium azide; phosphate buffer; acetic acid; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; sodium iodide; In tetrahydrofuran; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tetasy.2004.06.004

upstream raw materials:

4-iodobut-1-ene

tert-butyl (2R,3S)-6-oxo-2,3-diphenylmorpholine-4-carboxylate

Downstream raw materials:

(3S,5S,6R)-4-(tert-butoxycarbonyl)-5,6-diphenyl-3-(2'-carbonylethyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

tert-butyl (3S,5S,6R)-3-(2-((RS)oxiran-2-yl)ethyl)-2-oxo-5,6-diphenylmorpholine-4-carboxylate

(2S,5S)-5-hydroxylysine hydrochloride

(2S,5R)-5-hydroxylysine monohydrochloride

Refernces

• 1、 Allevi, Pietro,Anastasia, Mario. "A practical and simple synthesis of (2S,5R)- and (2S,5S)-5-hydroxylysine and of a related α-amino acid required for the synthesis of the collagen cross-link pyridinoline". . p. 2091 - 2096. Retrieved 2007/10/03.
• 2、 Williams, Robert M.,Yuan, Chenguang. "Asymmetric Synthesis of 2,6-Diaminopimelic Acids". . p. 6519 - 6527. Retrieved 2007/10/02.