2-N-acetyl-3,4-di-O-benzyl-6-O-prop-1-en-α-D-glucosaminopyranosyl-(1→3)-2-N-acetyl-4-O-benzyl-6-((N,N,-diisopropylamino)-2-cyanoethylphosphite)-α-D-glucosaminopyranosyl-(1→2)-benzyl (2R)-3-benzyloxypropanoate

Base Information

• Chemical Name: 2-N-acetyl-3,4-di-O-benzyl-6-O-prop-1-en-α-D-glucosaminopyranosyl-(1→3)-2-N-acetyl-4-O-benzyl-6-((N,N,-diisopropylamino)-2-cyanoethylphosphite)-α-D-glucosaminopyranosyl-(1→2)-benzyl (2R)-3-benzyloxypropanoate
• CAS No.: 1448013-24-8
• Molecular Formula: C₆₆H₈₃N₄O₁₅P
• Molecular Weight: 1203.38
• Mol file: 1448013-24-8.mol

Synonyms:2-N-acetyl-3,4-di-O-benzyl-6-O-prop-1-en-α-D-glucosaminopyranosyl-(1→3)-2-N-acetyl-4-O-benzyl-6-((N,N,-diisopropylamino)-2-cyanoethylphosphite)-α-D-glucosaminopyranosyl-(1→2)-benzyl (2R)-3-benzyloxypropanoate

Chemical Property of 2-N-acetyl-3,4-di-O-benzyl-6-O-prop-1-en-α-D-glucosaminopyranosyl-(1→3)-2-N-acetyl-4-O-benzyl-6-((N,N,-diisopropylamino)-2-cyanoethylphosphite)-α-D-glucosaminopyranosyl-(1→2)-benzyl (2R)-3-benzyloxypropanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-N-acetyl-3,4-di-O-benzyl-6-O-prop-1-en-α-D-glucosaminopyranosyl-(1→3)-2-N-acetyl-4-O-benzyl-6-((N,N,-diisopropylamino)-2-cyanoethylphosphite)-α-D-glucosaminopyranosyl-(1→2)-benzyl (2R)-3-benzyloxypropanoate

There total 20 articles about 2-N-acetyl-3,4-di-O-benzyl-6-O-prop-1-en-α-D-glucosaminopyranosyl-(1→3)-2-N-acetyl-4-O-benzyl-6-((N,N,-diisopropylamino)-2-cyanoethylphosphite)-α-D-glucosaminopyranosyl-(1→2)-benzyl (2R)-3-benzyloxypropanoate 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: 82.0%

2-N-acetyl-3,4-di-O-benzyl-6-O-prop-1-en-α-D-glucosaminopyranosyl-(1→3)-2-N-acetyl-4-O-benzyl-α-D-glucosaminopyranosyl-(1→2)-benzyl (2R)-3-benzyloxypropanoate (1448013-23-7) + N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite (102691-36-1) → 2-N-acetyl-3,4-di-O-benzyl-6-O-prop-1-en-α-D-glucosaminopyranosyl-(1→3)-2-N-acetyl-4-O-benzyl-6-((N,N,-diisopropylamino)-2-cyanoethylphosphite)-α-D-glucosaminopyranosyl-(1→2)-benzyl (2R)-3-benzyloxypropanoate (1448013-24-8)

Guidance literature:

With N,N'-diisopropylammonium tetrazolide; In dichloromethane; acetonitrile; at 0 - 20 ℃; for 3h; Molecular sieve;

DOI:10.1039/c3cc43545h

Reference yield:

2-N-acetyl-6-O-allyl-3,4-di-O-benzyl-α-D-glucosaminopyranosyl-(1→3)-2-N-acetyl-4-O-benzyl-6-O-levulinoyl-α-D-glucosaminopyranosyl-(1→2)-benzyl (2R)-3-benzyloxypropanoate (1448013-34-0) → 2-N-acetyl-3,4-di-O-benzyl-6-O-prop-1-en-α-D-glucosaminopyranosyl-(1→3)-2-N-acetyl-4-O-benzyl-6-((N,N,-diisopropylamino)-2-cyanoethylphosphite)-α-D-glucosaminopyranosyl-(1→2)-benzyl (2R)-3-benzyloxypropanoate (1448013-24-8)

Guidance literature:

Multi-step reaction with 3 steps

1: (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; hydrogen / tetrahydrofuran / 0.5 h

2: pyridine; hydrazine hydrate; acetic acid / dichloromethane / 0.42 h

3: N,N'-diisopropylammonium tetrazolide / dichloromethane; acetonitrile / 3 h / 0 - 20 °C / Molecular sieve

With pyridine; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; N,N'-diisopropylammonium tetrazolide; hydrogen; hydrazine hydrate; acetic acid; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1039/c3cc43545h

Reference yield:

benzyl (2R)-2-hydroxy-3-benzyloxypropanoate → 2-N-acetyl-3,4-di-O-benzyl-6-O-prop-1-en-α-D-glucosaminopyranosyl-(1→3)-2-N-acetyl-4-O-benzyl-6-((N,N,-diisopropylamino)-2-cyanoethylphosphite)-α-D-glucosaminopyranosyl-(1→2)-benzyl (2R)-3-benzyloxypropanoate (1448013-24-8)

Guidance literature:

Multi-step reaction with 7 steps

1: trimethylsilyl trifluoromethanesulfonate / dichloromethane; diethyl ether / 1 h / -20 - -10 °C / Molecular sieve

2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; aq. phosphate buffer / 1.5 h / 0 - 20 °C

3: trimethylsilyl trifluoromethanesulfonate / dichloromethane; diethyl ether / 1 h / -20 - -10 °C / Molecular sieve

4: pyridine / 24 h

5: (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; hydrogen / tetrahydrofuran / 0.5 h

6: pyridine; hydrazine hydrate; acetic acid / dichloromethane / 0.42 h

7: N,N'-diisopropylammonium tetrazolide / dichloromethane; acetonitrile / 3 h / 0 - 20 °C / Molecular sieve

With pyridine; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; trimethylsilyl trifluoromethanesulfonate; N,N'-diisopropylammonium tetrazolide; hydrogen; hydrazine hydrate; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; aq. phosphate buffer; diethyl ether; dichloromethane; acetonitrile;

DOI:10.1039/c3cc43545h

upstream raw materials:

2-N-acetyl-6-O-allyl-3,4-di-O-benzyl-α-D-glucosaminopyranosyl-(1→3)-2-N-acetyl-4-O-benzyl-6-O-levulinoyl-α-D-glucosaminopyranosyl-(1→2)-benzyl (2R)-3-benzyloxypropanoate

2-N-acetyl-3,4-di-O-benzyl-6-O-prop-1-en-α-D-glucosaminopyranosyl-(1→3)-2-N-acetyl-4-O-benzyl-α-D-glucosaminopyranosyl-(1→2)-benzyl (2R)-3-benzyloxypropanoate

N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite

O-benzyl-D-serine