[(2S,3S,4R,5R)-2-[(2E,4E,6E)-deca-2,4,6-trien-2-yl]-4-methoxy-5-methyloxan-3-yl] 2-aminoacetate

Base Information

• Chemical Name: [(2S,3S,4R,5R)-2-[(2E,4E,6E)-deca-2,4,6-trien-2-yl]-4-methoxy-5-methyloxan-3-yl] 2-aminoacetate
• CAS No.: 135357-96-9
• Molecular Formula: C19H31NO4
• Molecular Weight: 337.4537
• Wikidata: Q105105112
• Mol file: 135357-96-9.mol

Synonyms:restricticin;Ro 09-1470;Ro-09-1470

Chemical Property of [(2S,3S,4R,5R)-2-[(2E,4E,6E)-deca-2,4,6-trien-2-yl]-4-methoxy-5-methyloxan-3-yl] 2-aminoacetate

Chemical Property:

• Vapor Pressure: 8.7E-08mmHg at 25°C
• Boiling Point: 435.5°Cat760mmHg
• Flash Point: 123.8°C
• PSA: 70.78000
• Density: 1.04g/cm³
• LogP: 3.46590
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 337.22530847
• Heavy Atom Count: 24
• Complexity: 470

Purity/Quality:

RESTRICTICIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC=CC=CC=C(C)C1C(C(C(CO1)C)OC)OC(=O)CN
• Isomeric SMILES: CCC/C=C/C=C/C=C(\C)/[C@H]1[C@H]([C@@H]([C@@H](CO1)C)OC)OC(=O)CN

Technology Process of [(2S,3S,4R,5R)-2-[(2E,4E,6E)-deca-2,4,6-trien-2-yl]-4-methoxy-5-methyloxan-3-yl] 2-aminoacetate

There total 23 articles about [(2S,3S,4R,5R)-2-[(2E,4E,6E)-deca-2,4,6-trien-2-yl]-4-methoxy-5-methyloxan-3-yl] 2-aminoacetate 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: 61.0%

(2,2,2-Trichloro-ethoxycarbonylamino)-acetic acid (2S,3R,4S,5S)-4-methoxy-5-methyl-2-((1E,3E,5E)-1-methyl-nona-1,3,5-trienyl)-tetrahydro-pyran-3-yl ester → restricticin (135357-96-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 40 ℃; for 3h;

DOI:10.1016/S0040-4039(00)61633-7

Reference yield:

(2-Trimethylsilanyl-ethoxycarbonylamino)-acetic acid (2S,3R,4S,5S)-4-methoxy-5-methyl-2-((1E,3E,5E)-1-methyl-nona-1,3,5-trienyl)-tetrahydro-pyran-3-yl ester → restricticin (135357-96-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 40 ℃; for 2h; Yield given;

DOI:10.1016/0040-4039(96)01879-5

Reference yield:

((2S,3R,4S)-2-Benzyloxymethyl-4-methoxy-5-methylene-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane → restricticin (135357-96-9)

Guidance literature:

Multi-step reaction with 8 steps

1: H₂ / Pd-C / ethyl acetate

3: 75 percent / n-BuLi

4: 1.) DIBAH, 2.) water (pH 2-3) / 1.) toluene

5: 74 percent / n-BuLi / toluene / 5 °C

6: 32 percent / HCl(g) / methanol

7: 85 percent / ethyl-3-(3-dimethylamino)-propyl-carbodiimide, DMAP / CH₂Cl₂

8: 61 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 40 °C

With hydrogenchloride; dmap; n-butyllithium; tetrabutyl ammonium fluoride; water; hydrogen; diisobutylaluminium hydride; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; toluene;

DOI:10.1016/S0040-4039(00)61633-7

upstream raw materials:

(E)-4-(benzyloxy)-2-methylbut-2-enal

Restrictinol

(2S,3R,4S,5S)-2-((E)-3-Hydroxy-1-methyl-propenyl)-4-methoxy-5-methyl-tetrahydro-pyran-3-ol

(E)-3-((2S,3R,4S,5S)-3-Hydroxy-4-methoxy-5-methyl-tetrahydro-pyran-2-yl)-but-2-enal