1-O-benzyl-5-benzylamino-5-cyano-5-deoxy-2,3-O-(1-methylethylidene)-β-L-erythro-pentofuranose

Base Information

Chemical Name:1-O-benzyl-5-benzylamino-5-cyano-5-deoxy-2,3-O-(1-methylethylidene)-β-L-erythro-pentofuranose
CAS No.:1402155-09-2
Molecular Formula:C₂₃H₂₆N₂O₄
Molecular Weight:394.47
Hs Code.:

Synonyms:1-O-benzyl-5-benzylamino-5-cyano-5-deoxy-2,3-O-(1-methylethylidene)-β-L-erythro-pentofuranose

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Chemical Property of 1-O-benzyl-5-benzylamino-5-cyano-5-deoxy-2,3-O-(1-methylethylidene)-β-L-erythro-pentofuranose

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Technology Process of 1-O-benzyl-5-benzylamino-5-cyano-5-deoxy-2,3-O-(1-methylethylidene)-β-L-erythro-pentofuranose

There total 8 articles about 1-O-benzyl-5-benzylamino-5-cyano-5-deoxy-2,3-O-(1-methylethylidene)-β-L-erythro-pentofuranose 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: 80.0%

: 7677-24-9
trimethylsilyl cyanide

: 102919-04-0,102854-75-1
benzyl 2,3-O-isopropylidene-α-D-lyxo-pentodialdo-1,4-furanoside

: 100-46-9
benzylamine

: 1402155-09-2
1-O-benzyl-5-benzylamino-5-cyano-5-deoxy-2,3-O-(1-methylethylidene)-β-L-erythro-pentofuranose

Guidance literature:: benzyl 2,3-O-isopropylidene-α-D-lyxo-pentodialdo-1,4-furanoside; benzylamine; In acetonitrile; at 20 ℃; for 0.666667h; Molecular sieve;

trimethylsilyl cyanide; With copper(II) bis(trifluoromethanesulfonate); In acetonitrile; at 20 ℃; for 18h; optical yield given as %de; diastereoselective reaction; Molecular sieve;
DOI:10.1002/ejoc.201200587

Reference yield:

: 530-26-7
D-Mannose

: 1402155-09-2
1-O-benzyl-5-benzylamino-5-cyano-5-deoxy-2,3-O-(1-methylethylidene)-β-L-erythro-pentofuranose

Guidance literature:: Multi-step reaction with 5 steps

1.1: iodine / 2 h / 20 °C

2.1: 18-crown-6 ether; potassium hydroxide / tetrahydrofuran / 16 h / 20 °C

3.1: acetic acid / water / 18 h / 20 °C

4.1: silica-gel supported NaIO₄ / dichloromethane / 0.83 h / 20 °C

5.1: acetonitrile / 0.67 h / 20 °C / Molecular sieve

5.2: 18 h / 20 °C / Molecular sieve

With 18-crown-6 ether; iodine; acetic acid; potassium hydroxide; In tetrahydrofuran; dichloromethane; water; acetonitrile; 5.1: Strecker amino acid synthesis / 5.2: Strecker amino acid synthesis;
DOI:10.1002/ejoc.201200587

Reference yield:

: 7757-38-2,14131-84-1,23262-78-4,27108-13-0,33823-04-0,34685-42-2,57819-52-0,78039-08-4,78039-12-0,78964-16-6,94842-76-9,149342-31-4
2,3,5,6-di-O-isopropylidene-D-mannofuranose

: 1402155-09-2
1-O-benzyl-5-benzylamino-5-cyano-5-deoxy-2,3-O-(1-methylethylidene)-β-L-erythro-pentofuranose

Guidance literature:: Multi-step reaction with 4 steps

1.1: 18-crown-6 ether; potassium hydroxide / tetrahydrofuran / 16 h / 20 °C

2.1: acetic acid / water / 18 h / 20 °C

3.1: silica-gel supported NaIO₄ / dichloromethane / 0.83 h / 20 °C

4.1: acetonitrile / 0.67 h / 20 °C / Molecular sieve

4.2: 18 h / 20 °C / Molecular sieve

With 18-crown-6 ether; acetic acid; potassium hydroxide; In tetrahydrofuran; dichloromethane; water; acetonitrile; 4.1: Strecker amino acid synthesis / 4.2: Strecker amino acid synthesis;
DOI:10.1002/ejoc.201200587