2H-1,3-Oxazin-2-one, 6-(2,2-dimethyl-1,3-dioxolan-4-yl)tetrahydro-5-(phenylmethoxy)-4-(phenylmethyl)aminomethyl-, 4S-4.alpha.,5.alpha.,6.alpha.(S*)-

Base Information

• Chemical Name: 2H-1,3-Oxazin-2-one, 6-(2,2-dimethyl-1,3-dioxolan-4-yl)tetrahydro-5-(phenylmethoxy)-4-(phenylmethyl)aminomethyl-, 4S-4.alpha.,5.alpha.,6.alpha.(S*)-
• CAS No.: 163707-62-8
• Molecular Formula: C₂₄H₃₀N₂O₅
• Molecular Weight: 426.513
• Mol file: 163707-62-8.mol

Synonyms:2H-1,3-Oxazin-2-one, 6-(2,2-dimethyl-1,3-dioxolan-4-yl)tetrahydro-5-(phenylmethoxy)-4-(phenylmethyl)aminomethyl-, 4S-4.alpha.,5.alpha.,6.alpha.(S*)-

Chemical Property of 2H-1,3-Oxazin-2-one, 6-(2,2-dimethyl-1,3-dioxolan-4-yl)tetrahydro-5-(phenylmethoxy)-4-(phenylmethyl)aminomethyl-, 4S-4.alpha.,5.alpha.,6.alpha.(S*)-

Chemical Property:

• Boiling Point: 608.7±55.0 °C(Predicted)
• PKA: 10.78±0.70(Predicted)
• Density: 1.22±0.1 g/cm3(Predicted)

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2H-1,3-Oxazin-2-one, 6-(2,2-dimethyl-1,3-dioxolan-4-yl)tetrahydro-5-(phenylmethoxy)-4-(phenylmethyl)aminomethyl-, 4S-4.alpha.,5.alpha.,6.alpha.(S*)-

There total 18 articles about 2H-1,3-Oxazin-2-one, 6-(2,2-dimethyl-1,3-dioxolan-4-yl)tetrahydro-5-(phenylmethoxy)-4-(phenylmethyl)aminomethyl-, 4S-4.alpha.,5.alpha.,6.alpha.(S*)- 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: 13.0%

3-O-benzyl-2-t-butyloxycarbonylamino-2-deoxy-5,6-O-isopropylidene-1,4-di-O-methanesulfonyl-D-galactitol (163877-41-6) → 1,2-diamino-1,3-di-N,O-benzyl-2,4-N,O-carbonyl-1,2-deoxy-5,6-O-isopropylidene-D-glucitol (163707-62-8) + 2-amino-3-O-benzyl-2,4-N,O-carbonyl-2-deoxy-5,6-O-isopropylidene-1-O-methanesulfonyl-D-glucitol (163707-63-9) + 3-O-benzyl-1,4-(N-benzylimino)-2-t-butyloxycarbonylamino-5,6-O-isopropylidene-1,2,4-trideoxy-D-glucitol (163916-55-0)

Guidance literature:

With benzylamine; at 50 ℃; for 17h;

DOI:10.1016/S0040-4020(01)89338-8

Reference yield: 13.0%

3-O-benzyl-2-t-butyloxycarbonylamino-2-deoxy-5,6-O-isopropylidene-1,4-di-O-methanesulfonyl-D-galactitol (163877-41-6) + benzylamine (100-46-9) → 1,2-diamino-1,3-di-N,O-benzyl-2,4-N,O-carbonyl-1,2-deoxy-5,6-O-isopropylidene-D-glucitol (163707-62-8) + 2-amino-3-O-benzyl-2,4-N,O-carbonyl-2-deoxy-5,6-O-isopropylidene-1-O-methanesulfonyl-D-glucitol (163707-63-9) + 3-O-benzyl-1,4-(N-benzylimino)-2-t-butyloxycarbonylamino-5,6-O-isopropylidene-1,2,4-trideoxy-D-glucitol (163916-55-0)

Guidance literature:

at 50 ℃; for 17h;

DOI:10.1016/S0040-4020(01)89338-8

Reference yield:

benzyl bromide (100-39-0) → 1,2-diamino-1,3-di-N,O-benzyl-2,4-N,O-carbonyl-1,2-deoxy-5,6-O-isopropylidene-D-glucitol (163707-62-8)

Guidance literature:

Multi-step reaction with 16 steps

1: 80percent oily NaH / dimethylformamide / Ambient temperature

2: 10percent aq. HOAc / methanol / 7 h / Ambient temperature

3: NaBH₄ / methanol / 1 h / Ambient temperature

4: pyridine / Ambient temperature

5: 1M aq. NaOH / methanol / 7 h / Heating

6: KHCO₃ / dioxane; H₂O / Ambient temperature

7: 85 percent / 4-dimethylaminopyridine / pyridine / Ambient temperature

8: 97 percent / 4-dimethylaminopyridine / pyridine / Ambient temperature

9: 94 percent / triethylamine / dimethylformamide / 40 h / 120 °C

10: 1M aq. NaOH / dioxane / 15 h / Heating

11: KHCO₃ / dioxane; H₂O / Ambient temperature

12: 100 percent / pyridine / 4 h / Ambient temperature

13: 67 percent / p-toluenesulfonic acid, dimethoxypropane / acetone / 6 h / Ambient temperature

14: 91 percent / NaOMe / methanol / 3.5 h / Ambient temperature

15: 83 percent / 4-dimethylaminopyridine / pyridine / Ambient temperature

16: 11 percent / benzylamine / 17 h / 50 °C

With dmap; sodium hydroxide; sodium tetrahydroborate; dimethoxypropane; sodium methylate; sodium hydride; potassium hydrogencarbonate; toluene-4-sulfonic acid; acetic acid; triethylamine; benzylamine; In 1,4-dioxane; pyridine; methanol; water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4020(01)89338-8

upstream raw materials:

3-O-benzyl-2-t-butyloxycarbonylamino-2-deoxy-5,6-O-isopropylidene-1,4-di-O-methanesulfonyl-D-galactitol

benzylamine

benzyl bromide

2-methyl-(1,2-dideoxy-5,6-O-isopropylidene-α-D-glucofurano)-<2,1-d>-2-oxazoline

Refernces