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.alpha.(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.alpha.(R*)-
• CAS No.: 149625-46-7
• Molecular Formula: C₂₈H₃₈N₂O₅
• Molecular Weight: 482.62
• Mol file: 149625-46-7.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.alpha.(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.alpha.(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.alpha.(R*)-

There total 11 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.alpha.(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: 66.0%

3-O-benzyl-2-t-butyloxycarbonylamino-2-deoxy-5,6-O-isopropylidene-1,4-di-O-methanesulfonyl-D-glucitol (149625-45-6) + benzylamine (100-46-9) → 3-O-benzyl-1,4-(N-benzylimino)-2-t-butyloxycarbonylamino-1,2,4-trideoxy-5,6-O-isopropylidene-D-glucitol (149625-46-7)

Guidance literature:

at 70 ℃;

DOI:10.1016/S0040-4039(00)79188-X DOI:10.1016/S0040-4020(01)89338-8

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → 3-O-benzyl-1,4-(N-benzylimino)-2-t-butyloxycarbonylamino-1,2,4-trideoxy-5,6-O-isopropylidene-D-glucitol (149625-46-7)

Guidance literature:

Multi-step reaction with 3 steps

1: KHCO₃ / dioxane; H₂O / Ambient temperature

2: 82 percent / pyridine

3: 66 percent / 70 °C

With potassium hydrogencarbonate; In 1,4-dioxane; pyridine; water;

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

Reference yield:

2-methyl-(1,2-dideoxy-5,6-O-isopropylidene-α-D-glucofurano)-<2,1-d>-2-oxazoline (117177-19-2) → 3-O-benzyl-1,4-(N-benzylimino)-2-t-butyloxycarbonylamino-1,2,4-trideoxy-5,6-O-isopropylidene-D-glucitol (149625-46-7)

Guidance literature:

Multi-step reaction with 8 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: 82 percent / pyridine

8: 66 percent / 70 °C

With sodium hydroxide; sodium tetrahydroborate; sodium hydride; potassium hydrogencarbonate; acetic acid; In 1,4-dioxane; pyridine; methanol; water; N,N-dimethyl-formamide;

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-glucitol

benzylamine

di-tert-butyl dicarbonate

benzyl bromide

Downstream raw materials:

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