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

Base Information

Chemical Name:(R)-2-[(S)-1-phenylethylamino]-2-C-(3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl)acetonitrile
CAS No.:1352561-38-6
Molecular Formula:C₃₇H₄₀N₂O₄
Molecular Weight:576.736
Hs Code.:

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

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

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

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

: 1320325-11-8
3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl formaldehyde

: 2627-86-3
(S)-1-phenyl-ethylamine

: 75-86-5
2-hydroxy-2-methylpropanenitrile

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

: 1352561-38-6
(R)-2-[(S)-1-phenylethylamino]-2-C-(3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl)acetonitrile

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

2-hydroxy-2-methylpropanenitrile; With triethylamine; In tetrahydrofuran; at 0 - 20 ℃; optical yield given as %de; diastereoselective reaction; Molecular sieve; Inert atmosphere;
DOI:10.1016/j.carres.2011.10.023

Reference yield:

: 1320325-00-5
1-cyano-3,4,6-tri-O-benzyl-D-galactal

: 1352561-38-6
(R)-2-[(S)-1-phenylethylamino]-2-C-(3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl)acetonitrile

Guidance literature:: Multi-step reaction with 3 steps

1.1: palladium on activated charcoal; hydrogen / 760.05 Torr

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

3.1: tetrahydrofuran / 1 h / 0 °C / Molecular sieve; Inert atmosphere

3.2: 0 - 20 °C / Molecular sieve; Inert atmosphere

With pyridine; sodium hypophosphite; palladium on activated charcoal; hydrogen; acetic acid; In tetrahydrofuran; water; 3.1: Strecker reaction / 3.2: Strecker reaction;
DOI:10.1016/j.carres.2011.10.023

Reference yield:

: 100-39-0
benzyl bromide

: 1352561-38-6
(R)-2-[(S)-1-phenylethylamino]-2-C-(3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl)acetonitrile

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: tetrahydrofuran / 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 tetrahydrofuran; water; N,N-dimethyl-formamide; 4.1: Strecker reaction / 4.2: Strecker reaction;
DOI:10.1016/j.carres.2011.10.023