(R)-2-[(S)-1-phenylethylamino]-2-C-(3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)acetonitrile

Base Information

• Chemical Name: (R)-2-[(S)-1-phenylethylamino]-2-C-(3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)acetonitrile
• CAS No.: 1352561-99-9
• Molecular Formula: C₃₇H₄₀N₂O₄
• Molecular Weight: 576.736

Synonyms:(R)-2-[(S)-1-phenylethylamino]-2-C-(3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)acetonitrile

Chemical Property of (R)-2-[(S)-1-phenylethylamino]-2-C-(3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)acetonitrile

Chemical Property:

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Technology Process of (R)-2-[(S)-1-phenylethylamino]-2-C-(3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)acetonitrile

There total 5 articles about (R)-2-[(S)-1-phenylethylamino]-2-C-(3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)acetonitrile 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:

trimethylsilyl cyanide (7677-24-9) + (S)-1-phenyl-ethylamine (2627-86-3) + 3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl formaldehyde (208585-09-5) → (S)-2-[(S)-1-phenylethylamino]-2-C-(3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)acetonitrile + (R)-2-[(S)-1-phenylethylamino]-2-C-(3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)acetonitrile (1352561-99-9)

Guidance literature:

(S)-1-phenyl-ethylamine; 3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl formaldehyde; In dichloromethane; at 0 ℃; for 1h; Molecular sieve; Inert atmosphere;

trimethylsilyl cyanide; With methanol; In dichloromethane; at 0 - 20 ℃; optical yield given as %de; diastereoselective reaction; Molecular sieve; Inert atmosphere;

DOI:10.1016/j.carres.2011.10.023

Reference yield:

benzyl bromide (100-39-0) → (S)-2-[(S)-1-phenylethylamino]-2-C-(3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)acetonitrile + (R)-2-[(S)-1-phenylethylamino]-2-C-(3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)acetonitrile (1352561-99-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride / N,N-dimethyl-formamide

2.1: palladium on activated charcoal; hydrogen / 760.05 Torr

3.1: pyridine; sodium hypophosphite; acetic acid / water / 3 h / 20 °C / Cooling with ice

4.1: dichloromethane / 1 h / 0 °C / Molecular sieve; Inert atmosphere

4.2: 0 - 20 °C / Molecular sieve; Inert atmosphere

With pyridine; sodium hypophosphite; palladium on activated charcoal; hydrogen; sodium hydride; acetic acid; In dichloromethane; water; N,N-dimethyl-formamide; 4.1: Strecker reaction / 4.2: Strecker reaction;

DOI:10.1016/j.carres.2011.10.023

Reference yield:

β-D-glucopyranosyl cyanide (3737-60-8) → (S)-2-[(S)-1-phenylethylamino]-2-C-(3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)acetonitrile + (R)-2-[(S)-1-phenylethylamino]-2-C-(3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)acetonitrile (1352561-99-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride / N,N-dimethyl-formamide

2.1: palladium on activated charcoal; hydrogen / 760.05 Torr

3.1: pyridine; sodium hypophosphite; acetic acid / water / 3 h / 20 °C / Cooling with ice

4.1: dichloromethane / 1 h / 0 °C / Molecular sieve; Inert atmosphere

4.2: 0 - 20 °C / Molecular sieve; Inert atmosphere

With pyridine; sodium hypophosphite; palladium on activated charcoal; hydrogen; sodium hydride; acetic acid; In dichloromethane; water; N,N-dimethyl-formamide; 4.1: Strecker reaction / 4.2: Strecker reaction;

DOI:10.1016/j.carres.2011.10.023

upstream raw materials:

1-cyano-3,4,6-tri-O-benzyl-D-glucal

trimethylsilyl cyanide

(S)-1-phenyl-ethylamine

3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl formaldehyde

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