ethyl (2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-(1->4)-[(2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-(1->2)]-3-O-allyl-6-O-benzyl-1-thio-α-D-mannopyranoside

Base Information

Chemical Name:ethyl (2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-(1->4)-[(2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-(1->2)]-3-O-allyl-6-O-benzyl-1-thio-α-D-mannopyranoside
CAS No.:653597-52-5
Molecular Formula:C₇₀H₇₈O₁₃S
Molecular Weight:1159.45
Hs Code.:

Synonyms:ethyl (2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-(1->4)-[(2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-(1->2)]-3-O-allyl-6-O-benzyl-1-thio-α-D-mannopyranoside

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Chemical Property of ethyl (2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-(1->4)-[(2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-(1->2)]-3-O-allyl-6-O-benzyl-1-thio-α-D-mannopyranoside

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Technology Process of ethyl (2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-(1->4)-[(2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-(1->2)]-3-O-allyl-6-O-benzyl-1-thio-α-D-mannopyranoside

There total 5 articles about ethyl (2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-(1->4)-[(2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-(1->2)]-3-O-allyl-6-O-benzyl-1-thio-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: 61.0%

: 100-39-0
benzyl bromide

: 653597-51-4
ethyl (β-D-xylopyranosyl)-(1->4)-[(β-D-xylopyranosyl)-(1->2)]-3-O-allyl-6-O-benzyl-1-thio-α-D-mannopyranoside

: 653597-52-5
ethyl (2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-(1->4)-[(2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-(1->2)]-3-O-allyl-6-O-benzyl-1-thio-α-D-mannopyranoside

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 4h;
DOI:10.1081/CAR-120026459

Reference yield:

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

: 653597-52-5
ethyl (2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-(1->4)-[(2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-(1->2)]-3-O-allyl-6-O-benzyl-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: Bu₂SnO / methanol / 1 h / Heating

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

2.1: 75 percent / NaBH₃CN; molocular sieves 3 Angstroem / tetrahydrofuran / 0.5 h / 20 °C

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

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

4.1: 65 percent / NaOMe / methanol / 2 h / 20 °C

5.1: 61 percent / NaH / dimethylformamide / 4 h / 20 °C

With 2,6-di-tert-butyl-pyridine; 3 A molecular sieve; 4 A molecular sieve; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; di(n-butyl)tin oxide; sodium cyanoborohydride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1081/CAR-120026459

Reference yield:

: 319922-00-4
ethyl 3-O-allyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

: 653597-52-5
ethyl (2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-(1->4)-[(2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-(1->2)]-3-O-allyl-6-O-benzyl-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: 75 percent / NaBH₃CN; molocular sieves 3 Angstroem / tetrahydrofuran / 0.5 h / 20 °C

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

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

3.1: 65 percent / NaOMe / methanol / 2 h / 20 °C

4.1: 61 percent / NaH / dimethylformamide / 4 h / 20 °C

With 2,6-di-tert-butyl-pyridine; 3 A molecular sieve; 4 A molecular sieve; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; sodium cyanoborohydride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1081/CAR-120026459