(R)-2-((S)-1-phenylethylamino)-2-C-(3,4,6-tri-O-benzyl-2-deoxy-D-lyxo-hex-1-enopyranosyl)acetonitrile

Base Information

Chemical Name:(R)-2-((S)-1-phenylethylamino)-2-C-(3,4,6-tri-O-benzyl-2-deoxy-D-lyxo-hex-1-enopyranosyl)acetonitrile
CAS No.:1352561-35-3
Molecular Formula:C₃₇H₃₈N₂O₄
Molecular Weight:574.72
Hs Code.:

Synonyms:(R)-2-((S)-1-phenylethylamino)-2-C-(3,4,6-tri-O-benzyl-2-deoxy-D-lyxo-hex-1-enopyranosyl)acetonitrile

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Chemical Property of (R)-2-((S)-1-phenylethylamino)-2-C-(3,4,6-tri-O-benzyl-2-deoxy-D-lyxo-hex-1-enopyranosyl)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-D-lyxo-hex-1-enopyranosyl)acetonitrile

There total 6 articles about (R)-2-((S)-1-phenylethylamino)-2-C-(3,4,6-tri-O-benzyl-2-deoxy-D-lyxo-hex-1-enopyranosyl)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:

: 7677-24-9
trimethylsilyl cyanide

: 1352561-46-6
N-((S)-1-phenylethyl)-(3,4,6-tri-O-benzyl-2-deoxy-D-lyxo-hex-2-enopyranosyl)formaldimine

: (S)-2-((S)-1-phenylethylamino)-2-C-(3,4,6-tri-O-benzyl-2-deoxy-D-lyxo-hex-1-enopyranosyl)acetonitrile

: 1352561-35-3
(R)-2-((S)-1-phenylethylamino)-2-C-(3,4,6-tri-O-benzyl-2-deoxy-D-lyxo-hex-1-enopyranosyl)acetonitrile

Guidance literature:: With methanol; C₃₁H₅₀N₄O₄S; 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:

: 7677-24-9
trimethylsilyl cyanide

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

: 1-C-formyl-3,4,6-tri-O-benzyl-D-galactal

: (S)-2-((S)-1-phenylethylamino)-2-C-(3,4,6-tri-O-benzyl-2-deoxy-D-lyxo-hex-1-enopyranosyl)acetonitrile

: 1352561-35-3
(R)-2-((S)-1-phenylethylamino)-2-C-(3,4,6-tri-O-benzyl-2-deoxy-D-lyxo-hex-1-enopyranosyl)acetonitrile

Guidance literature:: (S)-1-phenyl-ethylamine; 1-C-formyl-3,4,6-tri-O-benzyl-D-galactal; 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:

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

: (S)-2-((S)-1-phenylethylamino)-2-C-(3,4,6-tri-O-benzyl-2-deoxy-D-lyxo-hex-1-enopyranosyl)acetonitrile

: 1352561-35-3
(R)-2-((S)-1-phenylethylamino)-2-C-(3,4,6-tri-O-benzyl-2-deoxy-D-lyxo-hex-1-enopyranosyl)acetonitrile

Guidance literature:: Multi-step reaction with 2 steps

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

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

2.2: 0 - 20 °C / Molecular sieve; Inert atmosphere

With pyridine; sodium hypophosphite; acetic acid; In dichloromethane; water; 2.1: Strecker reaction / 2.2: Strecker reaction;
DOI:10.1016/j.carres.2011.10.023