2-azidoethyl (2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-(1->2)-(4,6-di-O-benzyl-α-D-mannopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-α-D-mannopyranoside

Base Information

• Chemical Name: 2-azidoethyl (2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-(1->2)-(4,6-di-O-benzyl-α-D-mannopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-α-D-mannopyranoside
• CAS No.: 653597-58-1
• Molecular Formula: C₇₅H₈₁N₃O₁₅
• Molecular Weight: 1264.48
• Mol file: 653597-58-1.mol

Synonyms:2-azidoethyl (2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-(1->2)-(4,6-di-O-benzyl-α-D-mannopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-α-D-mannopyranoside

Chemical Property of 2-azidoethyl (2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-(1->2)-(4,6-di-O-benzyl-α-D-mannopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-azidoethyl (2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-(1->2)-(4,6-di-O-benzyl-α-D-mannopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-α-D-mannopyranoside

There total 14 articles about 2-azidoethyl (2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-(1->2)-(4,6-di-O-benzyl-α-D-mannopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-α-D-mannopyranoside 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: 73.0%

2-azidoethyl (2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-(1->2)-(3-O-allyl-4,6-di-O-benzyl-α-D-mannopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-α-D-mannopyranoside (653597-57-0) → 2-azidoethyl (2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-(1->2)-(4,6-di-O-benzyl-α-D-mannopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-α-D-mannopyranoside (653597-58-1)

Guidance literature:

With palladium dichloride; In methanol; ethanol; for 5h;

DOI:10.1081/CAR-120026459

Reference yield:

2-azidoethyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside (140428-83-7) → 2-azidoethyl (2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-(1->2)-(4,6-di-O-benzyl-α-D-mannopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-α-D-mannopyranoside (653597-58-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 99 percent / NaOMe / methanol / 20 °C

2.1: 707 mg / p-TsOH / acetonitrile / 60 °C

3.1: Bu₂SnO / methanol / 1 h / Heating

3.2: 612 mg / CsF / dimethylformamide / 20 °C

4.1: 85 percent / acetic acid / 3 h / 70 °C

5.1: 88 percent / NaH / dimethylformamide / 0 - 20 °C

6.1: 82 percent / DDQ / CH₂Cl₂; H₂O / 3 h / 0 °C

7.1: 91 percent / molecular sieves 4 Angstroem; (dimethyl)(methylthio)sulfonium triflate / diethyl ether / 3 h / 20 °C

8.1: 73 percent / PdCl₂ / methanol; ethanol / 5 h

With 4 A molecular sieve; sodium methylate; sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; acetic acid; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium dichloride; In methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1081/CAR-120026459

Reference yield:

S-ethyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside (142924-31-0) → 2-azidoethyl (2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-(1->2)-(4,6-di-O-benzyl-α-D-mannopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-α-D-mannopyranoside (653597-58-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: Bu₂SnO / methanol / 1 h / Heating

1.2: 86 percent / CsF / dimethylformamide / 20 °C

2.1: silver triflate; 2,6-di-tert-butylpyridine; molecular sieves 4 Angstroem / CH₂Cl₂; toluene / 1 h / -40 °C

2.2: Et₃N / toluene; CH₂Cl₂ / 0.25 h / -40 °C

3.1: 3.37 g / NaOMe / methanol / 4 h / 20 °C

4.1: 87 percent / NaH / dimethylformamide / 1 h / 0 °C

5.1: 39 percent / AlCl₃; BH₃*NMe₃; molecular sieves 4 Angstroem / diethyl ether; CH₂Cl₂ / 1 h / 0 °C

6.1: 91 percent / NaH / dimethylformamide / 4 h / 0 °C

7.1: 91 percent / molecular sieves 4 Angstroem; (dimethyl)(methylthio)sulfonium triflate / diethyl ether / 3 h / 20 °C

8.1: 73 percent / PdCl₂ / methanol; ethanol / 5 h

With aluminium trichloride; 2,6-di-tert-butyl-pyridine; trimethylamine-borane; 4 A molecular sieve; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; di(n-butyl)tin oxide; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; palladium dichloride; In methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1081/CAR-120026459

upstream raw materials:

2-azidoethyl (2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-(1->2)-(3-O-allyl-4,6-di-O-benzyl-α-D-mannopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-α-D-mannopyranoside

2-azidoethyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside

S-ethyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside

ethyl 3-O-allyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside