methyl 4-O-acetyl-3-O-benzyl-2-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-β-D-mannopyranoside

Base Information

Chemical Name:methyl 4-O-acetyl-3-O-benzyl-2-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-β-D-mannopyranoside
CAS No.:156917-64-5
Molecular Formula:C₂₇H₃₆O₁₄
Molecular Weight:584.574
Hs Code.:

Synonyms:methyl 4-O-acetyl-3-O-benzyl-2-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-β-D-mannopyranoside

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Chemical Property of methyl 4-O-acetyl-3-O-benzyl-2-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-β-D-mannopyranoside

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Technology Process of methyl 4-O-acetyl-3-O-benzyl-2-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-β-D-mannopyranoside

There total 6 articles about methyl 4-O-acetyl-3-O-benzyl-2-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-β-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:

: 40010-11-5,61277-64-3,65942-01-0,81371-52-0,81371-53-1,93714-01-3,108644-64-0,133268-63-0,133268-64-1,143005-10-1,143005-11-2
methyl β-D-glucopyranoside 3-benzyl ether

: 156917-64-5
methyl 4-O-acetyl-3-O-benzyl-2-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-β-D-mannopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: 75 percent / p-TsOH*H₂O / dimethylformamide / 16 h / 60 °C

2: 1.) Ac₂O, DMSO, 2.) Kieselgel 60, NaBH₄ / 1.) 20 h, 2.) CH₂Cl₂, MeOH, 0 deg C, 30 min

3: 89 percent / mol. sieves 4A, trimethylsilyl triflate / CH₂Cl₂ / 1.25 h / -40 °C

4: 69 percent / mol. sieves 3A, sodium cyanoborohydride, HCl/Et₂O / tetrahydrofuran / 2 h

5: 98 percent / pyridine / 16 h

6: 1.) 1,4-diazabicyclo<2.2.2>octane, tris(triphenylphosphine)rhodium(I) chloride, 2.) 1 M aq. HCl / 1.) EtOH, toluene, H₂O, reflux, 2 h, 2.) acetone, reflux, 30 min

With pyridine; 1,4-diaza-bicyclo[2.2.2]octane; hydrogenchloride; sodium tetrahydroborate; Wilkinson's catalyst; diethyl ether; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; 4 A molecular sieve; Kieselgel 60; acetic anhydride; sodium cyanoborohydride; toluene-4-sulfonic acid; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/0008-6215(94)80060-X

Reference yield:

: methyl 3-O-benzyl-4,6-O-prop-2-enylidene-2-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-β-D-mannopyranoside

: 156917-64-5
methyl 4-O-acetyl-3-O-benzyl-2-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-β-D-mannopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 69 percent / mol. sieves 3A, sodium cyanoborohydride, HCl/Et₂O / tetrahydrofuran / 2 h

2: 98 percent / pyridine / 16 h

3: 1.) 1,4-diazabicyclo<2.2.2>octane, tris(triphenylphosphine)rhodium(I) chloride, 2.) 1 M aq. HCl / 1.) EtOH, toluene, H₂O, reflux, 2 h, 2.) acetone, reflux, 30 min

With pyridine; 1,4-diaza-bicyclo[2.2.2]octane; hydrogenchloride; Wilkinson's catalyst; diethyl ether; 3 A molecular sieve; sodium cyanoborohydride; In tetrahydrofuran;
DOI:10.1016/0008-6215(94)80060-X

Reference yield:

: 156917-58-7
methyl 3-O-benzyl-4,6-O-prop-2-enylidene-β-D-glucopyranoside

: 156917-64-5
methyl 4-O-acetyl-3-O-benzyl-2-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-β-D-mannopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) Ac₂O, DMSO, 2.) Kieselgel 60, NaBH₄ / 1.) 20 h, 2.) CH₂Cl₂, MeOH, 0 deg C, 30 min

2: 89 percent / mol. sieves 4A, trimethylsilyl triflate / CH₂Cl₂ / 1.25 h / -40 °C

3: 69 percent / mol. sieves 3A, sodium cyanoborohydride, HCl/Et₂O / tetrahydrofuran / 2 h

4: 98 percent / pyridine / 16 h

5: 1.) 1,4-diazabicyclo<2.2.2>octane, tris(triphenylphosphine)rhodium(I) chloride, 2.) 1 M aq. HCl / 1.) EtOH, toluene, H₂O, reflux, 2 h, 2.) acetone, reflux, 30 min

With pyridine; 1,4-diaza-bicyclo[2.2.2]octane; hydrogenchloride; sodium tetrahydroborate; Wilkinson's catalyst; diethyl ether; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; 4 A molecular sieve; Kieselgel 60; acetic anhydride; sodium cyanoborohydride; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane;
DOI:10.1016/0008-6215(94)80060-X