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

Base Information

Chemical Name: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
CAS No.:653597-57-0
Molecular Formula:C₇₈H₈₅N₃O₁₅
Molecular Weight:1304.54
Hs Code.:

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 12 articles about 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 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: 91.0%

: 653597-43-4
2-azidoethyl 2,4,6-tri-O-benzyl-α-D-mannopyranoside

: 653597-49-0
ethyl (2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-(1->2)-3-O-allyl-4,6-di-O-benzyl-1-thio-α-D-mannopyranoside

: 653597-57-0
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

Guidance literature:: With 4 A molecular sieve; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; In diethyl ether; at 20 ℃; for 3h;
DOI:10.1081/CAR-120026459

Reference yield:

: 140428-83-7
2-azidoethyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside

: 653597-57-0
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

Guidance literature:: Multi-step reaction with 7 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

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; In methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1081/CAR-120026459

Reference yield:

: 142924-31-0
S-ethyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside

: 653597-57-0
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

Guidance literature:: Multi-step reaction with 7 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

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; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1081/CAR-120026459