Carbamic acid, 5-(2,2-dimethyl-1,3-dioxolan-4-yl)-4-(phenylmethoxy)-1-(phenylmethyl)-3-pyrrolidinyl-, 1,1-dimethylethyl ester, 3S-3.alpha.,4.beta.,5.beta.(R*)-

Base Information

• Chemical Name: Carbamic acid, 5-(2,2-dimethyl-1,3-dioxolan-4-yl)-4-(phenylmethoxy)-1-(phenylmethyl)-3-pyrrolidinyl-, 1,1-dimethylethyl ester, 3S-3.alpha.,4.beta.,5.beta.(R*)-
• CAS No.: 163916-55-0
• Molecular Formula: C₂₈H₃₈N₂O₅
• Molecular Weight: 482.62
• Mol file: 163916-55-0.mol

Synonyms:Carbamic acid, 5-(2,2-dimethyl-1,3-dioxolan-4-yl)-4-(phenylmethoxy)-1-(phenylmethyl)-3-pyrrolidinyl-, 1,1-dimethylethyl ester, 3S-3.alpha.,4.beta.,5.beta.(R*)-

Chemical Property of Carbamic acid, 5-(2,2-dimethyl-1,3-dioxolan-4-yl)-4-(phenylmethoxy)-1-(phenylmethyl)-3-pyrrolidinyl-, 1,1-dimethylethyl ester, 3S-3.alpha.,4.beta.,5.beta.(R*)-

Chemical Property:

• Boiling Point: 574.4±50.0 °C(Predicted)
• PKA: 11.45±0.60(Predicted)
• PSA: 69.26000
• Density: 1.17±0.1 g/cm3(Predicted)
• LogP: 4.82980

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Carbamic acid, 5-(2,2-dimethyl-1,3-dioxolan-4-yl)-4-(phenylmethoxy)-1-(phenylmethyl)-3-pyrrolidinyl-, 1,1-dimethylethyl ester, 3S-3.alpha.,4.beta.,5.beta.(R*)-

There total 18 articles about Carbamic acid, 5-(2,2-dimethyl-1,3-dioxolan-4-yl)-4-(phenylmethoxy)-1-(phenylmethyl)-3-pyrrolidinyl-, 1,1-dimethylethyl ester, 3S-3.alpha.,4.beta.,5.beta.(R*)- 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) → 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:

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: 13 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

Downstream raw materials:

2-acetamido-5,6-di-O-acetyl-3-O-benzyl-1,4-(N-benzylimino)-1,2,4-trideoxy-D-glucitol

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